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Hotels in Montaione

November 2026
December 2026

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Check prices for these dates

This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Where to stay in Montaione?

An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".
A hallway with a large painting of a rural scene, a cushioned bench, and a view of the outdoors through a glass door.
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.

1. Hotel le Macine

Hotel le Macine
Montaione
$84
$97 total
includes taxes & fees
Oct 27 - Oct 28
Hotel le Macine
A person performing a yoga pose on a wooden deck with a view of a landscape.
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.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

2. Castelfalfi

Castelfalfi
Montaione
$826
$920 total
includes taxes & fees
Oct 24 - Oct 25
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 tiled patio, surrounded by neatly trimmed hedges and tall trees.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A bedroom with a bed, a bedside table, a lamp, and a view of an outdoor dining area.

3. Borgo san Benedetto

Borgo san Benedetto
Montaione
$160
$182 total
includes taxes & fees
Nov 22 - Nov 23
Borgo san Benedetto
A two-story building with a tiled roof, surrounded by trees and a well-maintained lawn.
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.

4. Boccioleto Resort&Spa - Place of Charme

Boccioleto Resort&Spa - Place of Charme
Montaione
$64
$77 total
includes taxes & fees
Oct 29 - Oct 30
Boccioleto Resort&Spa - Place of Charme
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A restaurant with a wooden bar, tables set for dining, and a view of the outdoors.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.

5. Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$82
$94 total
includes taxes & fees
Oct 29 - Oct 30
Tenuta Castellare di Tonda
A stone building with a garden, two white lounge chairs, and a pergola.
A room with two wooden beds with floral bedding, a brick wall, a window, and a radiator.
A stone building with a sloped roof, surrounded by well-maintained grass and a few trees.
A dining area with a brick wall, a table with chairs, a vase of flowers, and a window with curtains.

6. Toscana Vacanze

Toscana Vacanze
MONTAIONE
$148
$267 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

7. Villa Sestilia

Villa Sestilia
Montaione
$162
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
A poolside area with lounge chairs and umbrellas, surrounded by a landscaped garden with red flowers.
A buffet setup with various food items and a seating area with wicker chairs and tables.
A bedroom with a bed, two windows, a stone wall, and a view of the countryside.
A large estate with multiple buildings, a swimming pool, and extensive vineyard fields.

8. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
$108
$124 total
includes taxes & fees
Nov 8 - Nov 9
Poderi Arcangelo
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
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.

9. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
$120
$138 total
includes taxes & fees
Oct 25 - Oct 26
LHP Certaldo Resort
A stone building with an arched entrance, ivy-covered walls, and potted plants.
A kitchen with a herringbone tile floor, a breakfast bar with fruit and bread, and a view of a garden through a glass door.
A cozy room with a glass door leading to a pool area, a wooden bench, and a table with glasses and a bottle.
A cozy kitchen with a wooden bench, a dining table, and a view of a garden through arched windows.

10. Mormoraia

Mormoraia
San Gimignano
$243
$273 total
includes taxes & fees
Nov 21 - Nov 22
Mormoraia
A bedroom with a large bed, two bedside tables, a mirror, and a chandelier.
A stone building with a tiled roof, outdoor seating area with lounge chairs, and a gravel path.
A bedroom with a bed, a lamp, a chandelier, and curtains.
A stone building with a swimming pool, outdoor seating, and trees.

11. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
$93
$108 total
includes taxes & fees
Nov 13 - Nov 14
Il Castagnolo Country B&B
A poolside view with lounge chairs and umbrellas, a clear sky, and a distant landscape.
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a view of trees.
An outdoor seating area with a table, two sofas, and an umbrella.
A modern indoor pool area with a glass wall, lounge chairs, and a jacuzzi.

12. Tenuta Bartoli

Tenuta Bartoli
San Gimignano
$459
$511 total
includes taxes & fees
Oct 25 - Oct 26
Tenuta Bartoli
A patio area with round tables and chairs, outdoor dining setup, and a view of a cityscape in the background.
A view through a window of a well-maintained garden with neatly trimmed hedges and tall trees.
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.

13. La Collegiata

La Collegiata
San Gimignano
$151
$174 total
includes taxes & fees
Oct 30 - Oct 31
La Collegiata
A pool area with lounge chairs and umbrellas, a view of a hilltop town with historic buildings.
An aerial view of a residential property with multiple buildings, a swimming pool, and a well-maintained garden.
A hotel room with a bed, a bedside table with a lamp, a small table with two glasses, and a chair.
A buffet table with various food items and a sign reading 'TORRELUCENT'.

14. Cappuccina Country Resort

Cappuccina Country Resort
San Gimignano
$191
$218 total
includes taxes & fees
Oct 24 - Oct 25
Cappuccina Country Resort
A round table with a white tablecloth, surrounded by metal chairs, under a white umbrella.
A cozy bar area with brick arches, white leather chairs, and a bar counter stocked with bottles.
A historic street with a hotel entrance featuring an arched doorway and potted plants.
A bedroom with a bed, a desk with a chair, a fireplace, and a window with a view of buildings.

15. Hotel L' Antico Pozzo San Gimignano

Hotel L' Antico Pozzo San Gimignano
San Gimignano City Centre
$103
$120 total
includes taxes & fees
Nov 4 - Nov 5
Hotel L' Antico Pozzo San Gimignano
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.
A lobby with a reception desk, a staircase, and seating areas.
A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.
A table set for dining with a view of a vineyard.

16. La Cisterna

La Cisterna
San Gimignano City Centre
$89
$105 total
includes taxes & fees
Nov 21 - Nov 22
La Cisterna
A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.
A restaurant with multiple tables and chairs, a wall decorated with plates, and a buffet area with food items.
A pool area with lounge chairs and a view of the countryside.
A stone building with a rustic garden, a hanging light fixture, and a gravel path.

17. il Casale del Cotone

il Casale del Cotone
San Gimignano
$198
$223 total
includes taxes & fees
Nov 1 - Nov 2
il Casale del Cotone
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.
An outdoor dining area with multiple tables and chairs, surrounded by buildings with balconies and a staircase.
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.

18. Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
San Gimignano
$165
$188 total
includes taxes & fees
Oct 24 - Oct 25
Hotel Casolare Le Terre Rosse
An outdoor courtyard with stone walls, arched doorways, and potted plants.
A courtyard with a hanging planter, potted plants, and a brick wall.
A pool with a view of a vineyard and hills.
A view of a traditional brick building with arched doorways and wooden shutters.

19. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
$86
$100 total
includes taxes & fees
Oct 27 - Oct 28
Residenza d'Epoca Palazzo Buonaccorsi
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 two-story building with a yellow facade, arched windows, and a garden with various plants and flowers.
A swimming pool with a view of a historic city on a hill.
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.

20. Agriturismo Il Segreto di Pietrafitta

Agriturismo Il Segreto di Pietrafitta
San Gimignano
$188
$212 total
includes taxes & fees
Oct 24 - Oct 25
Agriturismo Il Segreto di Pietrafitta
View all properties

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A person performing a yoga pose on a wooden deck with a view of a landscape.
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.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

Castelfalfi

Castelfalfi
Montaione
$1,020
per night
$1,133 total
includes taxes & fees
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 tiled patio, surrounded by neatly trimmed hedges and tall trees.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A bedroom with a bed, a bedside table, a lamp, and a view of an outdoor dining area.

Borgo san Benedetto

Borgo san Benedetto
Montaione
$8 off
$160
per night
$182 total
includes taxes & fees
Borgo san Benedetto
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

Villa Sestilia

Villa Sestilia
Montaione
$162
per night
$182 total
includes taxes & fees
Villa Sestilia
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

Check out pet-friendly hotels in Montaione

A person performing a yoga pose on a wooden deck with a view of a landscape.
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.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

Castelfalfi

Castelfalfi
Montaione
$826
$920 total
includes taxes & fees
Oct 24 - Oct 25
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 tiled patio, surrounded by neatly trimmed hedges and tall trees.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A bedroom with a bed, a bedside table, a lamp, and a view of an outdoor dining area.

Borgo san Benedetto

Borgo san Benedetto
Montaione
$160
$182 total
includes taxes & fees
Nov 22 - Nov 23
Borgo san Benedetto
An outdoor patio with a table and chairs, a stone building with a balcony, and a sign that reads "Cucco".
A hallway with a large painting of a rural scene, a cushioned bench, and a view of the outdoors through a glass door.
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 27 - Oct 28
Hotel le Macine
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A restaurant with a wooden bar, tables set for dining, and a view of the outdoors.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$82
$94 total
includes taxes & fees
Oct 29 - Oct 30
Tenuta Castellare di Tonda
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

Villa Sestilia

Villa Sestilia
Montaione
$162
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
A two-story building with a tiled roof, surrounded by trees and a well-maintained lawn.
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.

Boccioleto Resort&Spa - Place of Charme

Boccioleto Resort&Spa - Place of Charme
Montaione
$64
$77 total
includes taxes & fees
Oct 29 - Oct 30
Boccioleto Resort&Spa - Place of Charme
A stone building with a garden, two white lounge chairs, and a pergola.
A room with two wooden beds with floral bedding, a brick wall, a window, and a radiator.
A stone building with a sloped roof, surrounded by well-maintained grass and a few trees.
A dining area with a brick wall, a table with chairs, a vase of flowers, and a window with curtains.

Toscana Vacanze

Toscana Vacanze
MONTAIONE
$148
$267 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
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 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.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

Castelfalfi

Castelfalfi
Montaione
$826
$920 total
includes taxes & fees
Oct 24 - Oct 25
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 tiled patio, surrounded by neatly trimmed hedges and tall trees.
A stone building with a garden featuring tall trees, a swimming pool, and lounge chairs with blue umbrellas.
A bedroom with a bed, a bedside table, a lamp, and a view of an outdoor dining area.

Borgo san Benedetto

Borgo san Benedetto
Montaione
$160
$182 total
includes taxes & fees
Nov 22 - Nov 23
Borgo san Benedetto
A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.
A restaurant with a wooden bar, tables set for dining, and a view of the outdoors.
A swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$82
$94 total
includes taxes & fees
Oct 29 - Oct 30
Tenuta Castellare di Tonda
A two-story building with a tiled roof, surrounded by trees and a well-maintained lawn.
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.

Boccioleto Resort&Spa - Place of Charme

Boccioleto Resort&Spa - Place of Charme
Montaione
$64
$77 total
includes taxes & fees
Oct 29 - Oct 30
Boccioleto Resort&Spa - Place of Charme
A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.
A wine cellar with wooden shelves stocked with various bottles and glasses.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.
A swimming pool with a clear blue water, surrounded by greenery and a building in the background.

Villa Sestilia

Villa Sestilia
Montaione
$162
$182 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sestilia
A stone building with a garden, two white lounge chairs, and a pergola.
A room with two wooden beds with floral bedding, a brick wall, a window, and a radiator.
A stone building with a sloped roof, surrounded by well-maintained grass and a few trees.
A dining area with a brick wall, a table with chairs, a vase of flowers, and a window with curtains.

Toscana Vacanze

Toscana Vacanze
MONTAIONE
$148
$267 total
includes taxes & fees
Oct 30 - Oct 31
Toscana Vacanze
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
spa image
Spa
Spa
Family friendly image
Family friendly
Family friendly
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Farm
Farm
Apartment image
Apart­ment
Apart­ment
apart-hotel image
Apart hotel
Apart hotel
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Resort
Resort
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Villa
Villa
campsite image
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°
18°
26°
15°
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 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 two-story building with a yellow facade, arched windows, and a garden with various plants and flowers.
A swimming pool with a view of a historic city on a hill.
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.

Agriturismo Il Segreto di Pietrafitta

Agriturismo Il Segreto di Pietrafitta
San Gimignano

10/10 Exceptional

United States
Vicki
Agriturismo Il Segreto di Pietrafitta
A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.
A stone-walled room with a bench and a small shelf.
A swimming pool with clear water, surrounded by stone walls and lush greenery, overlooking a scenic landscape.
A round bar area with a central light fixture and a variety of bottles and glasses.

Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany
Volterra

10/10 Exceptional

United States
Nithiwadee
Borgo Pignano Volterra Tuscany
A table with a bottle of wine, two glasses, and a plate of food on a balcony overlooking a historic cityscape.
A reception sign for a taste and shop, surrounded by greenery and a gravel path leading to buildings.
A room with a window, a radiator, a chair, a table with a lamp and a book, and a bottle.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

Tenuta Guardastelle

Tenuta Guardastelle
San Gimignano

10/10 Exceptional

United States
Paige
Tenuta Guardastelle
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.
A restaurant with stone walls, wooden furniture, and a wine cellar.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti

10/10 Exceptional

United States
Patrick
Fattoria di Vegi
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A modern hotel room with a large bed, a wooden bench, a small table with towels and a hat, a plant, and a bathroom visible through an open door.
An outdoor patio with tables and chairs, umbrellas, and a view of the countryside.
An interior with a bar area, seating, and a large window.

Laqua Vineyard

Laqua Vineyard
Terricciola

10/10 Exceptional

United States
nocham
Laqua Vineyard
A stone building with a tiled pathway leading to a large planter.
A stone building with a tiled roof, arched windows, and a well-maintained lawn.
A bottle of wine and two glasses on a windowsill with a vineyard view.
A terrace with wicker furniture, a pool, and a vineyard view.

La pietra del cabreo

La pietra del cabreo
Greve in Chianti

10/10 Exceptional

United States
Russell
La pietra del cabreo
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

Castello La Leccia

Castello La Leccia
Castellina in Chianti

10/10 Exceptional

United States
Sarah
Castello La Leccia
A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.
A bedroom with a large bed, a bedside table, and a chair.
A pool area with a view of a hilly landscape.
A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti

10/10 Exceptional

United States
William
Borgo Del Cabreo
A person performing a yoga pose on a wooden deck with a view of a landscape.
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.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

Castelfalfi

Castelfalfi
Montaione

10/10 Exceptional

United States
Ann
Castelfalfi
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A spacious living room with a large window offering a view of the countryside. There are two armchairs, a sofa, and a coffee table with a vase of flowers.
An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.
A dining area with stone walls, wooden beams, and round tables set for a meal.

Villa Le Calvane

Villa Le Calvane
Montespertoli

10/10 Exceptional

United States
Anonymous traveler
Villa Le Calvane
A round table with a white tablecloth, two white chairs, and a vase of flowers on a terrace with a stone wall and a scenic view of green hills.
A spa area with a stone ceiling, a hot tub, and a seating area.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.
A poolside area with lounge chairs and a stone building in the background.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti

10/10 Exceptional

United States
Jacqueline
Palazzo Squarcialupi
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
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.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti

10/10 Exceptional

United States
Anonymous traveler
Locanda le Piazze
A stone building with an arched entrance, ivy-covered walls, and potted plants.
A kitchen with a herringbone tile floor, a breakfast bar with fruit and bread, and a view of a garden through a glass door.
A cozy room with a glass door leading to a pool area, a wooden bench, and a table with glasses and a bottle.
A cozy kitchen with a wooden bench, a dining table, and a view of a garden through arched windows.

Mormoraia

Mormoraia
San Gimignano

10/10 Exceptional

United States
Emily
Mormoraia
An aerial view of a historic estate with multiple buildings, a swimming pool, and terraced vineyards.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.
A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa

10/10 Exceptional

United States
Candy Perque
COMO Castello Del Nero
A stone building with a patio area featuring a table and chairs under a large umbrella.
A stone building with a garden, outdoor seating, and a large tree.
A spacious indoor area with arched windows, wooden furniture, and hanging plants.
A rectangular swimming pool with a tiled border, surrounded by lounge chairs and umbrellas, set against a backdrop of rolling hills and trees.

Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta

10/10 Exceptional

United States
Anonymous traveler
Relais Villa Olmo - Place of Charme
A pool area with lounge chairs and umbrellas, surrounded by greenery and buildings.
An aerial view of a vineyard estate with terraced fields, a swimming pool, and a curved building with a tiled roof.
A man and a woman in a restaurant with a stone wall and a wooden table.
A table set outdoors with wine glasses and cutlery, surrounded by greenery and trees.

Hotel Sovestro

Hotel Sovestro
San Gimignano

10/10 Exceptional

United States
Mikhail
Hotel Sovestro
A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.
A bedroom with a bed, bedside tables, a rug, and a view of the outdoors.
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".

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti
San Casciano in Val di Pesa

10/10 Exceptional

United States
Sarah
Salvadonica - Borgo del Chianti

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.