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

Hotels in Montaione

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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 stone building with a paved entrance and a decorative archway with red flowers.

A hotel room with a bathtub, a bed, a desk, and a window with curtains.

A buffet setup with various food items and a view of the outdoors through large windows.

1. Hotel le Macine

Montaione

$107

$122 total

includes taxes & fees

Oct 14 - Oct 15

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

A table set for dining outdoors with a view of the garden and trees.

2. Boccioleto Resort&Spa

Montaione

$87

$103 total

includes taxes & fees

Sep 28 - Sep 29

A cozy outdoor patio with stone flooring, wooden tables and chairs, and a variety of potted plants and flowers.

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

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.

3. Borgo san Benedetto

Montaione

$181

$206 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

4. Castelfalfi

Montaione

$838

$933 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 restaurant with a wooden bar, tables set for dining, and a view of the outdoors.

A room with a curved sofa, patterned walls, and a circular floor design.

A swimming pool with lounge chairs and a terracotta pot.

5. Tenuta Castellare di Tonda

Montaione

$104

$118 total

includes taxes & fees

Oct 8 - Oct 9

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.

6. Villa Sestilia

Montaione

$195

$217 total

includes taxes & fees

Oct 14 - Oct 15

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 table set for dining with a view of a vineyard.

A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.

7. La Cisterna

San Gimignano City Centre

$103

$120 total

includes taxes & fees

Oct 24 - Oct 25

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 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.

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

8. Hotel Casolare Le Terre Rosse

San Gimignano

$173

$197 total

includes taxes & fees

Oct 14 - Oct 15

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 pathway flanked by tall, slender trees leading to a distant point.

A spacious living area with a fireplace, comfortable seating, and an arched doorway.

9. Tenuta Bartoli

San Gimignano

$465

$518 total

includes taxes & fees

Oct 1 - Oct 2

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

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

An aerial view of a villa with a swimming pool, surrounded by lush greenery and terraced gardens.

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

10. Borgo Di Colleoli Resort

Palaia

$153

$173 total

includes taxes & fees

Sep 29 - Sep 30

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.

A bedroom with a bed, a desk with a chair, a fireplace, and a window with a view of buildings.

11. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

$127

$147 total

includes taxes & fees

Oct 18 - Oct 19

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

12. LHP Certaldo Resort

Certaldo

$119

$138 total

includes taxes & fees

Oct 25 - Oct 26

An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.

A gym with treadmills, weight machines, and free weights.

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.

13. Hotel Leon Bianco

San Gimignano City Centre

$128

$148 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

A wedding reception table set outdoors with floral arrangements and candles.

14. Relais Sassa al Sole

San Miniato

$212

$234 total

includes taxes & fees

Oct 2 - Oct 3

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

15. Relais Santa Chiara Hotel by Double Hospitality

San Gimignano

$106

$125 total

includes taxes & fees

Oct 25 - Oct 26

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 stone-walled room with a bench and a small shelf.

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

16. Borgo Pignano Volterra Tuscany

Volterra

$517

$575 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

An outdoor seating area with tables and chairs under a tent, surrounded by potted plants and a stone wall.

17. Hotel San Lino

Volterra

$101

$118 total

includes taxes & fees

Oct 22 - Oct 23

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 large estate with multiple buildings, a swimming pool, and extensive vineyard fields.

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

18. Poderi Arcangelo

San Gimignano

$126

$144 total

includes taxes & fees

Oct 23 - Oct 24

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

A stone-walled room with a hot tub, wooden beams, and a view of the outdoors.

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

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

19. La Collegiata

San Gimignano

$198

$225 total

includes taxes & fees

Oct 9 - Oct 10

A stone building with a swimming pool, outdoor seating, and trees.

A view through a window of a stone wall with two towers, one with a pointed roof and the other with a rounded top.

A stone building with a tiled roof, outdoor seating area with lounge chairs, and a gravel path.

A restaurant with a brick floor, white furniture, and a chalkboard menu.

20. Il Castagnolo Country B&B

San Gimignano

$118

$135 total

includes taxes & fees

Sep 30 - Oct 1

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Get last-minute hotel deals in Montaione and save more

Next weekend

Tenuta Castellare di Tonda

Montaione

$101

per night

$229 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 bedroom with a stone wall, a bed with floral bedding, two bedside lamps, and towels on the bed.

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

A brick house with a patio area featuring outdoor seating and a large umbrella.

Charming Retreat in Montaione

Montaione

$87

per night

$323 total

includes taxes & fees

Castelfalfi

Montaione

$1,334

per night

$2,958 total

includes taxes & fees

A swimming pool with sun loungers and umbrellas, surrounded by greenery and hills.

A yellow villa with a stone facade, a well-maintained lawn, and a large potted plant with red flowers in the foreground.

A black car parked on a gravel path with a stone wall and greenery in the background.

A balcony with a view of a green landscape, a potted plant, and a wooden pergola.

Agriturismo Belmonte Vacanze

Montaione

$20 off

$194

per night

$433 total

includes taxes & fees

Villa Sestilia

Montaione

$226

per night

$505 total

includes taxes & fees

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

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

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

A terrace with a view of a vineyard and a swimming pool.

Correggiolo Romantic Apartment Pool Montaione Toscana

Montaione

$228

per night

$710 total

includes taxes & fees

Borghetto Vitae

Montaione

$533

per night

$1,180 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

$838

$933 total

includes taxes & fees

Oct 23 - Oct 24

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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.

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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.

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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