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Hotels in Montaione

October 2026
5
November 2026

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This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Where to stay in Montaione?

A person performing a yoga pose on a wooden deck with a view of a landscape.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

1. Castelfalfi

Castelfalfi
Montaione
$829
$923 total
includes taxes & fees
Oct 23 - Oct 24
Castelfalfi
An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".
A buffet setup with various food items and a view of the outdoors through large windows.
A hotel room with a bathtub, a bed, a desk, and a window with curtains.
A stone building with a paved entrance and a decorative archway with red flowers.

2. Hotel le Macine

Hotel le Macine
Montaione
$84
$97 total
includes taxes & fees
Oct 8 - Oct 9
Hotel le Macine
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A stone building with a tiled patio, surrounded by neatly trimmed hedges and tall trees.

3. Borgo san Benedetto

Borgo san Benedetto
Montaione
$176
$201 total
includes taxes & fees
Oct 29 - Oct 30
Borgo san Benedetto
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A rural village with stone buildings, a paved road, and a vineyard in the foreground.

4. Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$90
$103 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta Castellare di Tonda
A kitchen with wooden cabinets, a dining table with chairs, and a hanging light fixture.
A courtyard with stone buildings, a grassy area, and a brick wall.
A bed with a headboard, two bedside lamps, and a patterned bedspread in a room with stone walls.
A stone building with a patio area featuring outdoor furniture and a table.

5. Toscana Vacanze

Toscana Vacanze
MONTAIONE
$165
$286 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
A restaurant with brick arches, wooden ceiling beams, and tables set for dining.
A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.
A table set for dining outdoors with a view of the garden and trees.

6. Boccioleto Resort&Spa

Boccioleto Resort&Spa
Montaione
$77
$91 total
includes taxes & fees
Oct 20 - Oct 21
Boccioleto Resort&Spa
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

7. Villa Sestilia

Villa Sestilia
Montaione
$163
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.
A pool area with lounge chairs and a view of the countryside.
A landscaped garden with a fountain, stone pathways, and a view of distant hills during twilight.
A stone building with a rustic garden, a hanging light fixture, and a gravel path.

8. il Casale del Cotone

il Casale del Cotone
San Gimignano
$173
$196 total
includes taxes & fees
Oct 31 - Nov 1
il Casale del Cotone
A dining area with a table set for four, overlooking a scenic landscape.
A buffet setup with various food items and a seating area with wicker chairs and tables.
A room with a bed, a wooden table, a chair, and a window with curtains.
A pool with a view of rolling hills and distant buildings.

9. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
$113
$130 total
includes taxes & fees
Nov 2 - Nov 3
Poderi Arcangelo
A stone building with an arched entrance, ivy-covered walls, and potted plants.
A room with a stone floor, a sofa, a chair, and a bookshelf.
A cozy kitchen with a wooden bench, a dining table, and a view of a garden through arched windows.
A cozy room with a glass door leading to a pool area, a wooden bench, and a table with glasses and a bottle.

10. Mormoraia

Mormoraia
San Gimignano
$277
$310 total
includes taxes & fees
Nov 4 - Nov 5
Mormoraia
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A courtyard with a lawn, seating area, and a weeping willow tree.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

11. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
$126
$145 total
includes taxes & fees
Oct 14 - Oct 15
LHP Certaldo Resort
A modern interior with a bar area, pendant lighting, and a vase with flowers on a counter.
A pathway flanked by tall, slender trees leading to a distant point.
A spacious living area with a fireplace, comfortable seating, and an arched doorway.
A dining area with a table set for two, overlooking a vineyard.

12. Tenuta Bartoli

Tenuta Bartoli
San Gimignano
$460
$512 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta Bartoli
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.
A historic square with stone buildings, a central fountain, and a tower.
A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.
A lobby with a reception desk, a staircase, and seating areas.

13. La Cisterna

La Cisterna
San Gimignano City Centre
$99
$116 total
includes taxes & fees
Nov 5 - Nov 6
La Cisterna
A table set for dining with a view of a hilltop town.
A stone-walled room with a large bathtub, wooden beams, and a view through a window.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery.
A stone-walled room with a hot tub, wooden beams, and a view of the outdoors.

14. La Collegiata

La Collegiata
San Gimignano
$121
$141 total
includes taxes & fees
Oct 30 - Oct 31
La Collegiata
A historic street with a hotel entrance featuring an arched doorway and potted plants.
An outdoor dining area with stone walls, potted plants, and a table set for two.
A cozy bar area with brick arches, white leather chairs, and a bar counter stocked with bottles.
A breakfast setting with croissants, fruit salad, and a cup of coffee on a table.

15. Hotel L' Antico Pozzo San Gimignano

Hotel L' Antico Pozzo San Gimignano
San Gimignano City Centre
$101
$118 total
includes taxes & fees
Nov 4 - Nov 5
Hotel L' Antico Pozzo San Gimignano
A stone building with a swimming pool, outdoor seating, and a waterfall feature.
A well-lit outdoor area with a stone building, tall trees, and a pathway leading to the entrance.
A gravel driveway leading to a stone building with a garden and tall trees.
A buffet setup with various food items and beverages, wooden crates, and a stone wall background.

16. Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery
San Gimignano
$164
$186 total
includes taxes & fees
Nov 1 - Nov 2
Tenuta Sovestro - Agriturismo e Winery
A stone building with a swimming pool, outdoor seating, and trees.
A restaurant with a brick floor, white furniture, and a chalkboard menu.
A stone building with a tiled roof, outdoor seating area with lounge chairs, and a gravel path.
A view through a window of a stone wall with two towers, one with a pointed roof and the other with a rounded top.

17. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
$117
$134 total
includes taxes & fees
Oct 6 - Oct 7
Il Castagnolo Country B&B
A dining table with a view of a pool and landscaped garden.
A table set for breakfast with a scenic view of hills and trees.
A hotel with a swimming pool, outdoor seating, and a view of the surrounding town.
A room with a fireplace, a table with a tray of food, and two lamps on either side of the fireplace.

18. Relais Santa Chiara Hotel by Double Hospitality

Relais Santa Chiara Hotel by Double Hospitality
San Gimignano
$105
$123 total
includes taxes & fees
Oct 20 - Oct 21
Relais Santa Chiara Hotel by Double Hospitality
A gated entrance with tall cypress trees, a paved path leading to a building with a yellow facade, and a mountain in the background.
A large estate with a swimming pool, surrounded by lush greenery and rolling hills.
A swimming pool with a stone building in the background, surrounded by trees and outdoor seating.
A bedroom with a bed, a desk, and a chair. There is a window with curtains, a painting on the wall, and a view of greenery outside.

19. Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
San Gimignano
$171
$195 total
includes taxes & fees
Oct 16 - Oct 17
Hotel Casolare Le Terre Rosse
An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.
A reception desk with a curved design, a framed painting above it, a potted plant to the right, and a window with curtains.
A desk with a book titled 'The Ancestors' Tale' by Richard Dawkins, a magazine, a pen, and a pair of glasses.
A bedroom with a bed, a desk, a chair, and a window with a view of buildings.

20. Hotel Leon Bianco

Hotel Leon Bianco
San Gimignano City Centre
$109
$126 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Leon Bianco
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A person performing a yoga pose on a wooden deck with a view of a landscape.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

Castelfalfi

Castelfalfi
Montaione
$1,321
per night
$2,930 total
includes taxes & fees
Castelfalfi
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A rural village with stone buildings, a paved road, and a vineyard in the foreground.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$100
per night
$226 total
includes taxes & fees
Tenuta Castellare di Tonda
Exterior
A stone building with a tiled roof, a chessboard in the foreground, and a bench to the right.
Private kitchen
Pool

Chalet in Tuscany With Pool and Scenic Views

Chalet in Tuscany With Pool and Scenic Views
Montaione
$160
per night
$357 total
includes taxes & fees
Sign in for extra savings
Chalet in Tuscany With Pool and Scenic Views
A poolside area with lounge chairs and umbrellas, a book on a towel, and a pool in the background.
A wine bottle, a glass of red wine, and sunflowers on a table.
A bedroom with a bed, a desk, a chair, a TV, and a window with curtains.
A garden path with a stone sculpture, a tall cypress tree, and flower beds.

Agriturismo Poggio Pistolese

Agriturismo Poggio Pistolese
Montaione
$21 off
$85
per night
$193 total
includes taxes & fees
Agriturismo Poggio Pistolese
Private kitchen
Living area
Private kitchen
Room

Borghetto Vitae

Borghetto Vitae
Montaione
$117 off
$528
per night
$1,168 total
includes taxes & fees
Borghetto Vitae
A swimming pool with sun loungers and umbrellas, surrounded by greenery and hills.
A black car parked on a gravel path with a stone wall and greenery in the background.
A yellow villa with a stone facade, a well-maintained lawn, and a large potted plant with red flowers in the foreground.
A dining area with a wooden table and chairs, a green sofa, and a kitchen in the background.

Agriturismo Belmonte Vacanze

Agriturismo Belmonte Vacanze
Montaione
$27 off
$260
per night
$578 total
includes taxes & fees
Agriturismo Belmonte Vacanze
A swimming pool with lounge chairs and umbrellas, surrounded by a hedge.
A two-story building with a patio area, outdoor seating, and a small dog.
A bedroom with a bed, bedside tables, a wardrobe, a mirror, and a dresser.
An outdoor dining area with brick walls, checkered tablecloths, and black metal chairs.

La Fornace Di Montaione

La Fornace Di Montaione
Montaione
La Fornace Di Montaione
An outdoor seating area with a table and chairs, a potted plant, and a building with a stone facade and green shutters.
A stone building with a bell tower, a paved courtyard, and a small tree.
A bedroom with a bed, a window with curtains, a wooden wardrobe, and a painting on the wall.
A wooden gazebo with benches on a grassy hill, surrounded by trees.

Agriturismo Il Poggio

Agriturismo Il Poggio
Montaione
Agriturismo Il Poggio
An outdoor seating area with tables and chairs, surrounded by greenery and a wooden pergola structure.
A two-story house with a stone facade, a balcony, and a well-maintained garden with hedges and trees.
A room with two beds, a wooden table, a chair, a window with curtains, and a cabinet.
A dining area with a wooden table and chairs, a television on a cabinet, and a view through a glass door.

La Fiaba At Belmonte

La Fiaba At Belmonte
Montaione
La Fiaba At Belmonte
An outdoor seating area with white plastic chairs and tables, a large umbrella, and a stone building with arched windows.
A brick house with a patio area featuring outdoor seating and a large umbrella.
A bedroom with a stone wall, a bed with floral bedding, two bedside lamps, and towels on the bed.
A rustic building with a brick facade, a pool area, and a wooden fence.

Charming Retreat in Montaione

Charming Retreat in Montaione
Montaione
$70
per night
$285 total
includes taxes & fees
Sign in for extra savings
Charming Retreat in Montaione
A stone building with a tiled roof, a wooden door, and a small garden with a palm tree.
A rustic kitchen with wooden cabinets, a dining table with chairs, and a staircase leading to an upper level.
A stone house with a brick chimney, surrounded by lush greenery and trees.
An outdoor seating area with white plastic chairs and tables, a large umbrella, and a stone building with arched windows.

Romola Retreat: Tuscan Escape

Romola Retreat: Tuscan Escape
Montaione
$68
per night
$281 total
includes taxes & fees
Sign in for extra savings
Romola Retreat: Tuscan Escape
A brick house with a patio area featuring outdoor seating and a large umbrella.
Dining
A patio area with outdoor seating, a pergola, and a view of a hilly landscape.
A paved garden pathway with neatly trimmed hedges and tall trees.

Montaione Oasis: Shared Villa

Montaione Oasis: Shared Villa
Montaione
$147
per night
$534 total
includes taxes & fees
Sign in for extra savings
Montaione Oasis: Shared Villa
Exterior
A swimming pool with a pergola, lounge chairs, and umbrellas.
A stone house with a brick chimney, surrounded by lush greenery and trees.
Private kitchen

Apartment in Tuscany With Pool and Garden

Apartment in Tuscany With Pool and Garden
Montaione
$126
per night
$281 total
includes taxes & fees
Sign in for extra savings
Apartment in Tuscany With Pool and Garden
Garden
Exterior
Dining
Dining

Apartment With Pool and Countryside Views

Apartment With Pool and Countryside Views
Montaione
$157
per night
$349 total
includes taxes & fees
Sign in for extra savings
Apartment With Pool and Countryside Views
A stone building with a tiled roof, a wooden door, and a small garden with a palm tree.
A chessboard set outdoors with large chess pieces, surrounded by greenery and trees.
An outdoor seating area with white plastic chairs and tables, a large umbrella, and a stone building with arched windows.
A swimming pool with a brick deck, a brick building with arched windows, and a white fence.

Farmhouse in Tuscany With Pool & Scenic Views

Farmhouse in Tuscany With Pool & Scenic Views
Montaione
$136
per night
$522 total
includes taxes & fees
Sign in for extra savings
Farmhouse in Tuscany With Pool & Scenic Views

Check out pet-friendly hotels in Montaione

A person performing a yoga pose on a wooden deck with a view of a landscape.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

Castelfalfi

Castelfalfi
Montaione
$829
$923 total
includes taxes & fees
Oct 23 - Oct 24
Castelfalfi
An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".
A buffet setup with various food items and a view of the outdoors through large windows.
A hotel room with a bathtub, a bed, a desk, and a window with curtains.
A stone building with a paved entrance and a decorative archway with red flowers.

Hotel le Macine

Hotel le Macine
Montaione
$84
$97 total
includes taxes & fees
Oct 8 - Oct 9
Hotel le Macine
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A stone building with a tiled patio, surrounded by neatly trimmed hedges and tall trees.

Borgo san Benedetto

Borgo san Benedetto
Montaione
$176
$201 total
includes taxes & fees
Oct 29 - Oct 30
Borgo san Benedetto
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A rural village with stone buildings, a paved road, and a vineyard in the foreground.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$90
$103 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta Castellare di Tonda
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

Villa Sestilia

Villa Sestilia
Montaione
$163
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
A restaurant with brick arches, wooden ceiling beams, and tables set for dining.
A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.
A table set for dining outdoors with a view of the garden and trees.

Boccioleto Resort&Spa

Boccioleto Resort&Spa
Montaione
$77
$91 total
includes taxes & fees
Oct 20 - Oct 21
Boccioleto Resort&Spa
View all properties

You may also like hotels with pools in Montaione

A person performing a yoga pose on a wooden deck with a view of a landscape.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

Castelfalfi

Castelfalfi
Montaione
$829
$923 total
includes taxes & fees
Oct 23 - Oct 24
Castelfalfi
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A stone building with a tiled patio, surrounded by neatly trimmed hedges and tall trees.

Borgo san Benedetto

Borgo san Benedetto
Montaione
$176
$201 total
includes taxes & fees
Oct 29 - Oct 30
Borgo san Benedetto
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
A restaurant with brick arches, wooden ceiling beams, and tables set for dining.
A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.
A table set for dining outdoors with a view of the garden and trees.

Boccioleto Resort&Spa

Boccioleto Resort&Spa
Montaione
$77
$91 total
includes taxes & fees
Oct 20 - Oct 21
Boccioleto Resort&Spa
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A rural village with stone buildings, a paved road, and a vineyard in the foreground.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$90
$103 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta Castellare di Tonda
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

Villa Sestilia

Villa Sestilia
Montaione
$163
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
View all properties

Go beyond your typical stay in Montaione

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Pool
Pool
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Pet friendly
Pet friendly
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Hot tub
Hot tub
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Spa
Spa
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Family friendly
Family friendly
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Farm
Farm
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Apart­ment
Apart­ment
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Apart hotel
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Villa
Villa
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Campsite
Campsite
Our prices for hotels in Montaione are cheapest in January

Price trends for hotels in Montaione

Pricing is based on two traveler single night rates
View properties in October

October

High 20°C / low 11°C. Sunny most days.
20°
11°
14°
7°
10°
3°
9°
2°
11°
2°
15°
4°
18°
8°
22°
11°
27°
15°
31°
18°
31°
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26°
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Monthly weather averages (˚C)

Top landmarks in Montaione

Castelfalfi Golf Course

9.6/10 (11 reviews)
You might want to practice your swing at Castelfalfi Golf Course, a golf course located 0.5 mi (0.9 km) from central Castelfalfi.
See properties

Monastery of San Vivaldo

9.2/10 (5 reviews)
Monastery of San Vivaldo is in the heart of San Vivaldo, so why not stop by during your stay.
See properties

Learn more about Montaione

The region around Montaione is home to attractions such as Castelfalfi Golf Course and Casa del Boccaccio.

See all hotels in Montaione
A historical building with a covered porch, columns, and a bell tower, surrounded by trees and a grassy area.

Check out reviews of Montaione hotels guests love

A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.
A round bar area with a central light fixture and a variety of bottles and glasses.
A stone building with a tiled roof, a gravel path leading to a wooden archway, and a sign reading "LA FONTE".
A stone-walled room with a bench and a small shelf.

Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany
Volterra

10/10 Exceptional

United States
Nithiwadee
Borgo Pignano Volterra Tuscany
A glass table with two wine glasses and a lantern on a patio with potted plants and a view of the city skyline at dusk.
A spacious living room with a high ceiling, stone walls, a wooden floor, a sofa, a coffee table, and a dog lying on the floor.
A two-story building with a yellow facade, arched windows, and a garden with various plants and flowers.
A rustic dining area with a stone fireplace, wooden beams, and a long table set for dining.

Agriturismo Il Segreto di Pietrafitta

Agriturismo Il Segreto di Pietrafitta
San Gimignano

10/10 Exceptional

United States
Vicki
Agriturismo Il Segreto di Pietrafitta
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.
A vineyard landscape with rows of grapevines and a person holding a glass.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti

10/10 Exceptional

United States
Anonymous traveler
Locanda le Piazze
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
A restaurant with brick arches, wooden ceiling beams, and tables set for dining.
A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.
A table set for dining outdoors with a view of the garden and trees.

Boccioleto Resort&Spa

Boccioleto Resort&Spa
Montaione

10/10 Exceptional

United States
Gadi
Boccioleto Resort&Spa
A person performing a yoga pose on a wooden deck with a view of a landscape.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A historic stone castle with a fortified wall, a courtyard, and surrounding lush green hills.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

Castelfalfi

Castelfalfi
Montaione

10/10 Exceptional

United States
Ann
Castelfalfi
An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".
A buffet setup with various food items and a view of the outdoors through large windows.
A hotel room with a bathtub, a bed, a desk, and a window with curtains.
A stone building with a paved entrance and a decorative archway with red flowers.

Hotel le Macine

Hotel le Macine
Montaione

10/10 Exceptional

United States
Michael
Hotel le Macine
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A rural village with stone buildings, a paved road, and a vineyard in the foreground.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione

10/10 Exceptional

United States
Thiago
Tenuta Castellare di Tonda
A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.
A pool area with lounge chairs and a view of the countryside.
A landscaped garden with a fountain, stone pathways, and a view of distant hills during twilight.
A stone building with a rustic garden, a hanging light fixture, and a gravel path.

il Casale del Cotone

il Casale del Cotone
San Gimignano

10/10 Exceptional

United States
Salvatore
il Casale del Cotone
An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.
A reception desk with a curved design, a framed painting above it, a potted plant to the right, and a window with curtains.
A desk with a book titled 'The Ancestors' Tale' by Richard Dawkins, a magazine, a pen, and a pair of glasses.
A bedroom with a bed, a desk, a chair, and a window with a view of buildings.

Hotel Leon Bianco

Hotel Leon Bianco
San Gimignano City Centre

10/10 Exceptional

United States
Todd
Hotel Leon Bianco
A couple sitting at an outdoor table with a view of the countryside.
A breakfast tray with bread, eggs, and a flower by a window.
A cozy room with a large window, a tray of breakfast items, and a bed with a blanket.
A rectangular swimming pool with lounge chairs and umbrellas, surrounded by tall trees and a clear sky.

Fonte de' Medici

Fonte de' Medici
San Casciano in Val di Pesa

10/10 Exceptional

United States
Sandra
Fonte de' Medici
A historic building with a courtyard, featuring a large tree, outdoor seating, and a well-lit entrance.
An outdoor swimming pool area with a stone wall, a pergola, and lounge chairs.
A spacious living room with a fireplace, a staircase, and a view of the outdoors.
A spacious room with a high arched brick ceiling, a central dining area with white table and chairs, and a patterned rug on the floor.

Giardino della Pieve Relais

Giardino della Pieve Relais
Cascina

10/10 Exceptional

United States
Daniel
Giardino della Pieve Relais
A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.
A swimming pool with clear water, surrounded by lounge chairs and trees.
A kitchen area with a marble countertop, a stone wall, and a sign reading "Cooking Class".
A bedroom with a bed, bedside tables, a rug, and a view of the outdoors.

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti
San Casciano in Val di Pesa

10/10 Exceptional

United States
Sarah
Salvadonica - Borgo del Chianti
An aerial view of a vineyard estate with terraced vineyards, a central building with multiple rooms, and a swimming pool.
A stone-walled building with a rustic appearance, surrounded by lush greenery and trees.
A stone building with a stone wall and gate, a circular stone bench with a swing, and a view of the landscape.
A rustic dining area with stone walls, wooden beams, and tiled flooring. There are several tables and chairs arranged for dining.

Hotel Pescille by Double Hospitality

Hotel Pescille by Double Hospitality
San Gimignano

10/10 Exceptional

United States
Jonathan
Hotel Pescille by Double Hospitality
A person sitting by a swimming pool with a stone building in the background.
A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.
A stone building with a wooden door and an arched window.
An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais
Tavarnelle Val di Pesa

10/10 Exceptional

United States
Alyssa
Hotel Borgo di Cortefreda Relais
A pool with a view of a lush valley and distant buildings.
A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.
A courtyard with stone buildings, arched doorways, and potted plants.
A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti

10/10 Exceptional

United States
Scott
Castello Vicchiomaggio
A stone building with a swimming pool, outdoor seating, and trees.
A restaurant with a brick floor, white furniture, and a chalkboard menu.
A stone building with a tiled roof, outdoor seating area with lounge chairs, and a gravel path.
A view through a window of a stone wall with two towers, one with a pointed roof and the other with a rounded top.

Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano

10/10 Exceptional

United States
Anonymous traveler
Il Castagnolo Country B&B
A spacious indoor area with arched windows, wooden furniture, and hanging plants.
An outdoor dining area with tables set for a meal, large windows, and a stone wall in the background.
A stone pathway leading to a terrace with potted plants and flowers, overlooking a hillside with houses.
A swimming pool with a clear blue water surface, surrounded by a brick deck and a grassy area with trees.

Relais Villa Olmo

Relais Villa Olmo
Impruneta

10/10 Exceptional

United States
Anonymous traveler
Relais Villa Olmo
Outdoor pool
A dining area with a brick fireplace, a table set with plates and bowls, and a bookshelf with books and decorative items.
A kitchen counter with various food items and kitchenware.
A room with a bed, bedside table, lamp, and a window with curtains.

Residenza Il Colle

Residenza Il Colle
Impruneta

10/10 Exceptional

United States
Alessandro
Residenza Il Colle

Frequently Asked Questions

What accommodations do travelers like in Montaione?

Guests like Castelfalfi, Boccioleto Resort&Spa and Tenuta Castellare di Tonda.

Can I book a refundable hotel in Montaione?

If you're looking for the flexibility to change your plans to Montaione, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Montaione if I want a vacation home instead of a hotel?

If you're looking for a good alternative to a hotel, look over our selection of 49 vacation homes. You can also book one of 115 apartments or 59 villas.

What will the weather in Montaione be like during my trip?

August and July are typically the warmest months in Montaione when the average temp is 73°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.

Why should I book my Montaione hotel with Hotels.com?

There are lots of reasons to book your Montaione trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.