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 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.

A hallway with a large painting of a rural scene, a cushioned bench, and a view of the outdoors through a glass door.

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 restaurant with brick arches, wooden ceiling beams, and tables set for dining.

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

A swimming pool with four lounge chairs, a view of a forested hill, and a tower on top.

2. Boccioleto Resort&Spa

Montaione

$87

$103 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 person in a pool with water jets, surrounded by a natural landscape and mountains in the background.

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.

3. 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 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.

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

4. Tenuta Castellare di Tonda

Montaione

$104

$118 total

includes taxes & fees

Oct 8 - Oct 9

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 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.

5. Borgo san Benedetto

Montaione

$181

$206 total

includes taxes & fees

Oct 25 - Oct 26

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.

6. Villa Sestilia

Montaione

$195

$217 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 historic square with stone buildings, a central fountain, and a tower.

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

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.

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.

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.

A dining area with a table set for two, overlooking a vineyard.

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 narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

A staircase with a wooden handrail and black balusters, leading to an upper floor.

A rustic room with exposed brick walls, a piano, and a dining table set with white tableware.

A rustic room with a stone ceiling, a bench, white tables, and a window with red curtains.

10. Hotel Il Castello

Certaldo Alto

$133

$152 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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

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

11. Borgo Di Colleoli Resort

Palaia

$153

$173 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

13. Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

$127

$147 total

includes taxes & fees

Oct 18 - Oct 19

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

A room with a stone floor, a sofa, a chair, and a bookshelf.

14. Mormoraia

San Gimignano

$300

$335 total

includes taxes & fees

Sep 29 - Sep 30

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

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

A room with a fireplace, a table with a tray of food, and two lamps on either side of the fireplace.

A hotel with a swimming pool, outdoor seating, and a view of the surrounding town.

15. Relais Santa Chiara Hotel by Double Hospitality

San Gimignano

$106

$125 total

includes taxes & fees

Oct 25 - Oct 26

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

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

16. Relais Sassa al Sole

San Miniato

$212

$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 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.

A swimming pool with clear water, surrounded by stone walls and lush greenery, overlooking a scenic landscape.

17. Borgo Pignano Volterra Tuscany

Volterra

$517

$575 total

includes taxes & fees

Oct 25 - Oct 26

A dining area with a table set for four, overlooking a scenic landscape.

A pool with a view of rolling hills and distant buildings.

A buffet setup with various food items and a seating area with wicker chairs and tables.

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

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.

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

19. Hotel San Lino

Volterra

$101

$118 total

includes taxes & fees

Oct 21 - Oct 22

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

San Gimignano City Centre

$128

$148 total

includes taxes & fees

Oct 18 - Oct 19

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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 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.

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

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 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

$184

per night

$413 total

includes taxes & fees

Villa Sestilia

Montaione

$226

per night

$505 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 trees and a building in the background.

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

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.

Correggiolo Romantic Apartment Pool Montaione Toscana

Montaione

$228

per night

$710 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