A historical building with a covered porch, columns, and a bell tower, surrounded by trees and a grassy area.

Hotels in Montaione

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

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 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.

1. Hotel le Macine

Montaione

$107

$122 total

includes taxes & fees

Oct 1 - Oct 2

A modern bathroom with a hot tub, a glass shower enclosure, and a brick wall.

A two-story building with a tiled roof, a central entrance, and a small balcony.

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.

2. Boccioleto Resort&Spa

Montaione

$98

$115 total

includes taxes & fees

Sep 28 - Sep 29

A person performing a yoga pose on a wooden deck with a view of a landscape.

A spacious interior with arched brick ceilings, a central dining area, and a cozy seating arrangement.

A modern hotel lobby with a reflective floor, arched seating areas, and a central column.

A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

3. Castelfalfi

Montaione

$839

$934 total

includes taxes & fees

Oct 23 - Oct 24

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 rural village with stone buildings, a paved road, and a vineyard in the foreground.

A restaurant with a wooden bar, tables set for dining, and a view of the outdoors.

4. Tenuta Castellare di Tonda

Montaione

$104

$117 total

includes taxes & fees

Oct 27 - Oct 28

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 stone building with a tiled patio, surrounded by neatly trimmed hedges and tall trees.

A bedroom with a bed, a bedside table, a lamp, and a view of an outdoor dining area.

5. Borgo san Benedetto

Montaione

$182

$207 total

includes taxes & fees

Oct 25 - Oct 26

A wine cellar with wooden shelves stocked with various bottles and glasses.

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.

6. Villa Sestilia

Montaione

$195

$218 total

includes taxes & fees

Oct 12 - Oct 13

A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent 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.

A table set for dining with a view of a vineyard.

7. La Cisterna

San Gimignano City Centre

$95

$111 total

includes taxes & fees

Oct 28 - Oct 29

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 kitchen with a herringbone tile floor, a breakfast bar with fruit and bread, and a view of a garden through a glass door.

8. Mormoraia

San Gimignano

$280

$314 total

includes taxes & fees

Oct 20 - Oct 21

A gated entrance with tall cypress trees, a paved path leading to a building with a yellow facade, and a mountain in the background.

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

A swimming pool with a stone building in the background, surrounded by trees and outdoor seating.

A large estate with a swimming pool, surrounded by lush greenery and rolling hills.

9. Hotel Casolare Le Terre Rosse

San Gimignano

$173

$197 total

includes taxes & fees

Oct 14 - Oct 15

A large building with a swimming pool, surrounded by greenery and outdoor lighting.

A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.

A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

10. LHP Certaldo Resort

Certaldo

$120

$138 total

includes taxes & fees

Oct 12 - Oct 13

A modern interior with a bar area, pendant lighting, and a vase with flowers on a counter.

An outdoor seating area with a table, two sofas, and an umbrella.

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.

11. Tenuta Bartoli

San Gimignano

$466

$518 total

includes taxes & fees

Oct 1 - Oct 2

A restaurant with brick ceilings, glass bar counters, and multiple seating areas.

A courtyard with outdoor seating, a Christmas tree, and a building with arched windows and a tiled roof.

A stone building with an arched entrance, outdoor seating, and a gravel courtyard.

A bar area with a long counter, shelves with bottles, and a brick ceiling.

12. Borgo Di Colleoli Resort

Palaia

$153

$173 total

includes taxes & fees

Sep 30 - Oct 1

A garden with tall cypress trees, a variety of flowering plants, and a clear sky.

A well-maintained garden with a stone pathway leading to a house with a tiled roof and a porch.

A spa room with a hot tub, wooden flooring, and a decorative window.

A villa with a swimming pool, surrounded by lush greenery and hills.

13. Relais Sassa al Sole

San Miniato

$213

$234 total

includes taxes & fees

Oct 2 - Oct 3

A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.

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.

A stone building with a tiled roof, a gravel path leading to a wooden archway, and a sign reading "LA FONTE".

14. Borgo Pignano Volterra Tuscany

Volterra

$518

$575 total

includes taxes & fees

Oct 22 - Oct 23

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.

An outdoor dining area with stone walls, potted plants, and a table set for two.

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

San Gimignano City Centre

$127

$147 total

includes taxes & fees

Oct 4 - Oct 5

A table set for dining with a view of a hilltop town.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery.

A view through a window of a well-maintained garden with neatly trimmed hedges and tall trees.

A stone-walled room with a large bathtub, wooden beams, and a view through a window.

16. La Collegiata

San Gimignano

$198

$226 total

includes taxes & fees

Oct 9 - Oct 10

A dining table with a view of a pool and landscaped garden.

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.

A garden area with potted plants, a red scooter, and a white umbrella.

17. Relais Santa Chiara Hotel by Double Hospitality

San Gimignano

$106

$125 total

includes taxes & fees

Oct 20 - Oct 21

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

A yellow building with stone pillars, multiple windows, and a statue in the garden.

18. Villa San Lucchese

Poggibonsi

$125

$144 total

includes taxes & fees

Oct 2 - Oct 3

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 pool with a view of rolling hills and distant buildings.

A bedroom with a bed, a desk, a TV, and a window with curtains.

19. Poderi Arcangelo

San Gimignano

$126

$144 total

includes taxes & fees

Oct 23 - Oct 24

A stone building with a sign reading "hotel s.ino" and a door with a wrought iron gate.

An outdoor patio with stone walls, a stone lamp post, and a table with chairs.

A narrow street with stone buildings, a wooden bench with flowers, and a cobblestone path.

A hotel lobby with a wooden reception desk, a black leather sofa, and a dining area in the background.

20. Hotel San Lino

Volterra

$102

$119 total

includes taxes & fees

Oct 21 - Oct 22

View all properties

Get last-minute hotel deals in Montaione and save more

Next weekend

Tenuta Castellare di Tonda

Montaione

$110

per night

$250 total

includes taxes & fees

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 rustic building with a brick facade, a pool area, and a wooden fence.

A chessboard set up in a garden with a building in the background.

Charming Retreat in Montaione

Montaione

$84

per night

$316 total

includes taxes & fees

Castelfalfi

Montaione

$1,336

per night

$2,962 total

includes taxes & fees

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 dining area with a wooden table and chairs, a green sofa, and a kitchen 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.

Agriturismo Belmonte Vacanze

Montaione

$19 off

$185

per night

$413 total

includes taxes & fees

Villa Sestilia

Montaione

$227

per night

$505 total

includes taxes & fees

Borghetto Vitae

Montaione

$119 off

$534

per night

$1,182 total

includes taxes & fees

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

A modern living room with a dining area, wooden flooring, a sofa, a coffee table, and a large window.

A large, two-story house with a tiled roof, surrounded by lush greenery and vineyards.

A modern kitchen with wooden cabinets, a dining area with a round table, and a built-in bench.

Correggiolo Romantic Apartment Pool Montaione Toscana

Montaione

$228

per night

$711 total

includes taxes & fees

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

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

Montaione

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.

Montaione

$195

$218 total

includes taxes & fees

Oct 12 - Oct 13

View all properties

Go beyond your typical stay in Montaione

Our prices for hotels in Montaione are cheapest in January

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

Check out reviews of Montaione hotels guests love

Castelfalfi

Montaione

10/10 Exceptional

Ann

Hotel le Macine

Montaione

10/10 Exceptional

Michael

Boccioleto Resort&Spa

Montaione

10/10 Exceptional

We stayed at Boccioleto Resort & Spa for five nights with our two kids and absolutely loved it. The hotel is stunning, surrounded by greenery, with spacious rooms and a pool overlooking breathtaking views. The staff is impeccable—always warm, attentive, and genuinely committed to making every guest feel special. You can really sense the team’s effort to create an unforgettable experience. Breakfast was delicious, and if we had more time, we would have gladly extended our stay.

Gadi