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Hotels in Montaione

October 2026
10
November 2026

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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
$825
$918 total
includes taxes & fees
Oct 30 - Oct 31
Castelfalfi
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 stone building with a paved entrance and a decorative archway with red flowers.
A buffet setup with various food items and a view of the outdoors through large windows.

2. Hotel le Macine

Hotel le Macine
Montaione
$83
$96 total
includes taxes & fees
Oct 14 - Oct 15
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 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
$176
$200 total
includes taxes & fees
Nov 5 - Nov 6
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 restaurant with a wooden bar, tables set for dining, and a view of the outdoors.

4. Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione
$90
$102 total
includes taxes & fees
Oct 11 - Oct 12
Tenuta Castellare di Tonda
A kitchen with wooden cabinets, a dining table with chairs, and a hanging light fixture.
A stone building with a patio area featuring outdoor furniture and a table.
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.

5. Toscana Vacanze

Toscana Vacanze
MONTAIONE
$148
$267 total
includes taxes & fees
Nov 3 - Nov 4
Toscana Vacanze
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
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.
A two-story building with a tiled roof, a central entrance, and a small balcony.

6. Boccioleto Resort&Spa - Place of Charme

Boccioleto Resort&Spa - Place of Charme
Montaione
$74
$88 total
includes taxes & fees
Oct 20 - Oct 21
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 swimming pool with a clear blue water, surrounded by greenery and a building in the background.
A rustic dining area with stone walls, wooden tables, and hanging light fixtures.
A bedroom with a large ornate mirror, a wooden dresser with decorative items, and a bed with white bedding.

7. Villa Sestilia

Villa Sestilia
Montaione
$162
$182 total
includes taxes & fees
Nov 5 - Nov 6
Villa Sestilia
A dining area with a table set for four, overlooking a scenic landscape.
A large estate with multiple buildings, a swimming pool, and extensive vineyard fields.
A buffet setup with various food items and a seating area with wicker chairs and tables.
A cozy living room with leather armchairs, a fireplace, and a stone wall.

8. Poderi Arcangelo

Poderi Arcangelo
San Gimignano
$108
$124 total
includes taxes & fees
Nov 8 - Nov 9
Poderi Arcangelo
A stone building with a tiled roof, surrounded by well-maintained gardens and vineyards.
A stone building with a rustic garden, a hanging light fixture, and a gravel path.
A pool area with lounge chairs and a view of the countryside.
A restaurant with multiple tables and chairs, a wall decorated with plates, and a buffet area with food items.

9. il Casale del Cotone

il Casale del Cotone
San Gimignano
$155
$177 total
includes taxes & fees
Nov 2 - Nov 3
il Casale del Cotone
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 courtyard with a lawn, seating area, and a weeping willow tree.

10. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
$127
$147 total
includes taxes & fees
Oct 18 - Oct 19
LHP Certaldo Resort
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.
A table set for dining with a view of a vineyard.
A lobby with a reception desk, a staircase, and seating areas.
A historic square with stone buildings, a central fountain, and a tower.

11. La Cisterna

La Cisterna
San Gimignano City Centre
$99
$116 total
includes taxes & fees
Nov 7 - Nov 8
La Cisterna
A modern interior with a bar area, pendant lighting, and a vase with flowers on a counter.
A dining area with a table set for two, overlooking a vineyard.
A spacious living area with a fireplace, comfortable seating, and an arched doorway.
An outdoor seating area with a table, two sofas, and an umbrella.

12. Tenuta Bartoli

Tenuta Bartoli
San Gimignano
$458
$510 total
includes taxes & fees
Oct 13 - Oct 14
Tenuta Bartoli
A stone building with an arched entrance, ivy-covered walls, and potted plants.
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.
A room with a stone floor, a sofa, a chair, and a bookshelf.

13. Mormoraia

Mormoraia
San Gimignano
$275
$308 total
includes taxes & fees
Oct 20 - Oct 21
Mormoraia
A table set for dining with a view of a hilltop town.
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.

14. La Collegiata

La Collegiata
San Gimignano
$159
$182 total
includes taxes & fees
Oct 30 - Oct 31
La Collegiata
A stone building with a swimming pool, outdoor seating, and a waterfall feature.
A rustic stone building with a wooden ceiling and a view of a vineyard.
A well-lit outdoor area with a stone building, tall trees, and a pathway leading to the entrance.
A buffet setup with various food items and beverages, wooden crates, and a stone wall background.

15. Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery
San Gimignano
$153
$174 total
includes taxes & fees
Nov 8 - Nov 9
Tenuta Sovestro - Agriturismo e Winery
A stone building with a swimming pool, outdoor seating, and trees.
A bedroom with a bed, a lamp, a chandelier, and curtains.
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.

16. Il Castagnolo Country B&B

Il Castagnolo Country B&B
San Gimignano
$116
$133 total
includes taxes & fees
Oct 12 - Oct 13
Il Castagnolo Country B&B
A historic street with a hotel entrance featuring an arched doorway and potted plants.
A breakfast setting with croissants, fruit salad, and a cup of coffee on a table.
A cozy bar area with brick arches, white leather chairs, and a bar counter stocked with bottles.
An outdoor dining area with stone walls, potted plants, and a table set for two.

17. 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 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 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.
An outdoor dining area with multiple tables and chairs, surrounded by buildings with balconies and a staircase.

18. Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse
San Gimignano
$171
$195 total
includes taxes & fees
Oct 24 - Oct 25
Hotel Casolare Le Terre Rosse
A garden with tall cypress trees, a variety of flowering plants, and a clear sky.
A spa room with a hot tub, wooden flooring, and a decorative window.
A well-maintained garden with a stone pathway leading to a house with a tiled roof and a porch.
A villa with a swimming pool, surrounded by lush greenery and hills.

19. Relais Sassa al Sole

Relais Sassa al Sole
San Miniato
$209
$230 total
includes taxes & fees
Oct 18 - Oct 19
Relais Sassa al Sole
A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.
A bedroom with a bed, a nightstand, a vase with dried plants, and a wall mural of a landscape.
A dining table set with plates, cutlery, and glasses, surrounded by potted plants and a view of trees.
A vineyard estate with terraced fields, a central building with a swimming pool, and a road leading through the property.

20. Hotel Le Colline

Hotel Le Colline
San Gimignano
$94
$110 total
includes taxes & fees
Oct 27 - Oct 28
Hotel Le Colline
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Go beyond your typical stay in Montaione

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Pet friendly
Pet friendly
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Pool
Pool
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Hot tub
Hot tub
spa image
Spa
Spa
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Family friendly
Family friendly
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Villa
Villa
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Resort
Resort
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Farm
Farm
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Apart­ment
Apart­ment
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Apart hotel
Apart hotel
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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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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 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 hallway with a large painting of a rural scene, a cushioned bench, and a view of the outdoors through a glass door.
A stone building with a paved entrance and a decorative archway with red flowers.
A buffet setup with various food items and a view of the outdoors through large windows.

Hotel le Macine

Hotel le Macine
Montaione

10/10 Exceptional

United States
Michael
Hotel le Macine
A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.
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.
A two-story building with a tiled roof, a central entrance, and a small balcony.

Boccioleto Resort&Spa - Place of Charme

Boccioleto Resort&Spa - Place of Charme
Montaione

10/10 Exceptional

United States
Gadi
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 swimming pool with lounge chairs and a terracotta pot.
A room with a curved sofa, patterned walls, and a circular floor design.
A restaurant with a wooden bar, tables set for dining, and a view of the outdoors.

Tenuta Castellare di Tonda

Tenuta Castellare di Tonda
Montaione

10/10 Exceptional

United States
Thiago
Tenuta Castellare di Tonda
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 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".

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 swimming pool with a view of a historic city on a hill.
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 table with a bottle of wine, two glasses, and a plate of food on a balcony overlooking a historic cityscape.
A room with a window, a radiator, a chair, a table with a lamp and a book, and a bottle.
A reception sign for a taste and shop, surrounded by greenery and a gravel path leading to buildings.
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 poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
An interior with a bar area, seating, and a large window.
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.

Laqua Vineyard

Laqua Vineyard
Terricciola

10/10 Exceptional

United States
nocham
Laqua Vineyard
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 restaurant with stone walls, wooden furniture, and a wine cellar.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti

10/10 Exceptional

United States
Patrick
Fattoria di Vegi
A stone building with a circular window and a door, surrounded by purple flowers.
A terrace with wicker furniture, a pool, and a vineyard view.
A stone building with a tiled pathway leading to a large planter.
A bottle of wine and two glasses on a windowsill with 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 pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
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 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 rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.
A pool area with a view of a hilly landscape.

Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti

10/10 Exceptional

United States
William
Borgo Del Cabreo
A stone building with a swimming pool, outdoor seating, and a waterfall feature.
A rustic stone building with a wooden ceiling and a view of a vineyard.
A well-lit outdoor area with a stone building, tall trees, and a pathway leading to the entrance.
A buffet setup with various food items and beverages, wooden crates, and a stone wall background.

Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery
San Gimignano

10/10 Exceptional

United States
Jennifer Olson
Tenuta Sovestro - Agriturismo e Winery
An outdoor dining area with wicker chairs and tables, white tablecloths, 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.
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A bar area with a dark bar counter, red chairs, and a fireplace.

Villa Le Calvane

Villa Le Calvane
Montespertoli

10/10 Exceptional

United States
Anonymous traveler
Villa Le Calvane
A stone building with an arched entrance, ivy-covered walls, and potted plants.
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.
A room with a stone floor, a sofa, a chair, and a bookshelf.

Mormoraia

Mormoraia
San Gimignano

10/10 Exceptional

United States
Emily
Mormoraia
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 vineyard landscape with rows of grapevines and a person holding a glass.
A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti

10/10 Exceptional

United States
Anonymous traveler
Locanda le Piazze

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.