Hotels in Montecastelli

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Where to stay in Montecastelli?

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

A well-lit outdoor bar area with a wooden structure, surrounded by lush greenery and stone pathways.

A swimming pool with lounge chairs and a pergola, surrounded by a garden and a building with a tiled roof.

A breakfast buffet with various pastries, fruits, and beverages.

1. Villa Sabolini

Colle di Val d'Elsa

$81

$93 total

includes taxes & fees

Nov 3 - Nov 4

A courtyard with outdoor seating, potted plants, and a building with a tiled roof.

A hotel room with a large bed, a bedside table with a lamp, a small desk, and a chair.

A restaurant with tables and chairs, a kitchen area, and a large window offering a view of trees.

A residential area with houses, a parking lot, and a street lamp.

2. Hotel Foresteria Volterra

Volterra

$91

$106 total

includes taxes & fees

Oct 19 - Oct 20

A stone staircase leading to a gated entrance, surrounded by lush greenery and a well-maintained lawn.

A rustic stone building with a small patio area featuring a terracotta pot with flowers, a metal chair, and a small table.

A swimming pool at night with a stone building in the background.

A buffet table with various food items and glass containers, set in an outdoor area with a wooden ceiling and a view of trees.

3. Tenuta Decimo

San Gimignano

$50

$60 total

includes taxes & fees

Oct 25 - Oct 26

A poolside area with lounge chairs and umbrellas, surrounded by stone tiles and trees.

A stone structure with a tiled roof, surrounded by lush greenery and purple wisteria vines.

An aerial view of a property with a swimming pool, multiple buildings, and a well-maintained lawn.

4. Agriturismo Nerbona

Colle di Val d'Elsa

$98

$110 total

includes taxes & fees

Oct 7 - Oct 8

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.

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

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

5. Hotel San Lino

Volterra

$100

$117 total

includes taxes & fees

Oct 16 - Oct 17

A clear pool with visible mineral deposits, a pebble beach, and a mountainous landscape in the background.

A rustic interior with exposed brick walls, a stone fireplace, and wooden beams. There are leather sofas, a round table, and potted plants.

An interior with a brick archway, stone walls, and modern seating.

An open window with a view of a mountainous landscape and a flower box on the windowsill.

6. VIN Hotel - La Meridiana

Montieri

$132

$145 total

includes taxes & fees

Oct 19 - Oct 20

A stone building with a sign reading "Vin Hotel." There are potted plants in front of the entrance.

A dining area with a stone wall, a spiral staircase, and floral upholstered chairs.

A lobby with a round table, a cream-colored sofa, and a decorative lamp.

A dining area with a round table and chairs, a vase with flowers, and a view of a stone building through an archway.

7. Hotel Volterra In Superior

Volterra

$111

$127 total

includes taxes & fees

Oct 11 - Oct 12

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 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.

8. Hotel Casolare Le Terre Rosse

San Gimignano

$171

$195 total

includes taxes & fees

Oct 16 - Oct 17

A swimming pool with lounge chairs and a stone building with a view of the mountains at sunset.

A covered patio with outdoor seating, stone walls, and a view of the landscape.

A restaurant with arched brick ceilings and wooden tables, featuring a stone wall and large windows.

A bedroom with a brick ceiling, a large bed with a red bedspread, a wooden headboard, a TV mounted on the wall, and a window with curtains.

9. Albergo Villa Rioddi

Volterra

$81

$95 total

includes taxes & fees

Oct 26 - Oct 27

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.

A hotel entrance with a glass door, a welcome mat, and two potted plants.

A bar area with a large mirror, shelves with bottles, a clock, and a patterned floor.

A bar area with shelves of liquor bottles, a coffee machine, and a tray with tea sets and pastries.

10. Albergo Etruria

Volterra

$100

$116 total

includes taxes & fees

Oct 18 - Oct 19

A courtyard with a statue, stone walls, and a reception sign.

A spacious room with a high ceiling, wooden beams, and a chandelier. There are tables and chairs arranged for dining, and a wine rack filled with bottles.

An outdoor dining area with tables and chairs, surrounded by trees and a stone wall.

A narrow cobblestone street flanked by stone buildings with arched windows and a central potted plant.

11. Relais Della Rovere

Colle di Val d'Elsa

$129

$147 total

includes taxes & fees

Oct 30 - Oct 31

A gated entrance with steps leading up to a gate, surrounded by greenery and potted plants.

A two-story building with a balcony, potted plants, and a gravel driveway.

A window with curtains, a view of a green landscape with hills and a stone structure.

A hallway with checkered flooring, wooden doors, and a radiator.

12. Villa Porta all'Arco

Volterra

$163

$185 total

includes taxes & fees

Oct 6 - Oct 7

A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.

A spacious lobby with a reception desk, a staircase with a glass railing, and a wooden floor.

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

A bar area with wooden bar stools, a counter with bottles, and a tiled floor.

13. Hotel La Vecchia Cartiera

Colle di Val d'Elsa

$83

$95 total

includes taxes & fees

Oct 7 - Oct 8

An aerial view of a vineyard estate with terraced vineyards, a central building with multiple rooms, and a swimming pool.

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

A rustic dining area with stone walls, wooden beams, and tiled flooring. There are several tables and chairs arranged for dining.

A stone-walled building with a rustic appearance, surrounded by lush greenery and trees.

14. Hotel Pescille by Double Hospitality

San Gimignano

$113

$131 total

includes taxes & fees

Oct 6 - Oct 7

A dining table with plates of food, a vase with flowers, and a view of a green landscape through large windows.

A bedroom with a four-poster bed, a balcony with a view, and a bedside table with a lamp.

A covered courtyard with stone columns, a brick floor, and a grassy area.

A swimming pool with a curved edge, surrounded by lush greenery and a clear sky.

15. Hotel Girifalco - Nature & Relax

Massa Marittima

$52

$69 total

includes taxes & fees

Oct 19 - Oct 20

A rustic stone building with a covered patio area featuring outdoor seating.

A restaurant with multiple tables set for dining, featuring a rustic wooden ceiling and stone walls.

A swimming pool with white lounge chairs and a view of rolling hills.

An outdoor courtyard with a stone archway, a tiled pathway, and a view of a building in the background.

16. Agrihotel Il Palagetto

Volterra

$107

$123 total

includes taxes & fees

Oct 13 - Oct 14

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

An arched entrance to a building with a tiled floor and a staircase leading inside.

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

A dining area with wooden chairs and tables, a chandelier, and potted plants.

17. Palazzo Pacini

Colle di Val d'Elsa

$150

$167 total

includes taxes & fees

Oct 6 - Oct 7

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

An outdoor patio with stone flooring, a table with chairs, and potted plants.

A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

18. Hotel Borgo San Luigi

Monteriggioni

$119

$139 total

includes taxes & fees

Nov 4 - Nov 5

A hotel with a pool, outdoor seating, and a mountainous backdrop.

An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.

An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.

A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.

19. Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

$889

$980 total

includes taxes & fees

Nov 5 - Nov 6

A table with a bottle of wine, two glasses, a lamp, and a potted plant by a window with floral curtains.

A pool area with lounge chairs and umbrellas, surrounded by a stone deck and lush greenery.

A stone building with a garden, a bench, and a covered area.

A stone building with a wooden door and window, potted plants, and a metal lantern.

20. La Canonica di San Michele

Monteriggioni

$102

$118 total

includes taxes & fees

Oct 18 - Oct 19

View all properties

Go beyond your typical stay in Montecastelli

Check out reviews of Montecastelli hotels guests love

Villa Sabolini

Colle di Val d'Elsa

10/10 Exceptional

We came to this hotel unexpectedly and were so happy we found it. The staff are truly exceptional, friendly, attentive, accommodating, effective, welcoming. We arrived due to my wife having emergency surgery in Siena, we were supposed to be in Venice, and this hotel staff went to work making sure we were taken care of. The grounds are stunning as well, an amazing place to recover after surgery. The pool is beautiful and the restaurant is fantastic. I truly have enjoyed each meal I have had. The...

Mark

Agriturismo Nerbona

Colle di Val d'Elsa

10/10 Exceptional

Veronica

VIN Hotel - La Meridiana

Montieri

10/10 Exceptional

John

Albergo Villa Rioddi

Volterra

10/10 Exceptional

Got lots of information on where to travel around the area. Very helpful with questions (where to park, how to get to places etc.) I booked this hotel bc of the breakfast and it did NOT DISSAPOINT! So many local dishes and eggs, and then breakfast dessert with a choice of 4-5 cakes everyday! It was a little hike from the town not very well marked but could easily drive and find parking (Luka will tell you where's it free/cheap/convenient) Spent a day at the pool looking at volterra and...

Kriste

Castello di Casole, A Belmond Hotel, Tuscany

Casole d'Elsa

10/10 Exceptional

Nicest hotel that we stayed at in Italy. Exceptional service and they strive to be upscale and deliver. Impeccable views, grounds, rooms, and restaurant. Almost felt too nice to be true-- blend of older style with new updates. A bit Disney-fied in feel that it seems to cater to mostly Americans and few locals. However, this means no hassles, broken fixtures, etc. (but it is a very different feel like a California spa vs. an old Italy village hotel). Only minor note is that it is a bit removed...

Jerry

Hotel Volterra In Superior

Volterra

10/10 Exceptional

Lone Lady

A covered patio area with stone walls, wooden beams, and outdoor furniture.

A room with a blue sofa, a dining table with chairs, a potted plant, and a view through a glass door to the outside.

A long banquet table with chairs, a chandelier, and draped fabric on a stone wall.

A large, historic building complex with multiple structures, surrounded by lush green fields and trees, under a partly cloudy sky.

Casale San Galgano

Chiusdino

10/10 Exceptional

Jose Manuel

Albergo Etruria

Volterra

10/10 Exceptional

Steve

Palazzo Pacini

Colle di Val d'Elsa

10/10 Exceptional

Simply charming. Located just a block from the Old Town and surrounded by medieval buildings, churches, and towers. Everything was perfect; the breakfast was delicious and made to order. The fruit, bread, and jams were fresh—no preservatives or pre-packaged products. The person in charge of the kitchen was very kind and attentive. The rooms were lovely, featuring antique furniture, and ours offered incredible views of the Tuscan landscape. We were treated like royalty. Furthermore, the location...

Anaisa

A stone building with a courtyard, surrounded by lush greenery and a hillside.

A stone building with a balcony, surrounded by lush greenery and a view of distant hills.

A window with white curtains, a view of buildings, and greenery.

A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.

Relais Le Macine di Stigliano

Sovicille

10/10 Exceptional

jorge

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 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.

Borgo Pignano Volterra Tuscany

Volterra

10/10 Exceptional

Nithiwadee

Hotel San Lino

Volterra

10/10 Exceptional

Todd

La Canonica di San Michele

Monteriggioni

10/10 Exceptional

Erin

Hotel Casolare Le Terre Rosse

San Gimignano

10/10 Exceptional

charles

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

San Gimignano

10/10 Exceptional

Mikhail

Hotel Borgo San Luigi

Monteriggioni

10/10 Exceptional

James

A pool area with lounge chairs and umbrellas, surrounded by stone walls and greenery.

A cozy living room with a fireplace, a comfortable sofa, a wooden coffee table, and a bookshelf.

A stone building with a tiled roof, a small attached structure, and a well-maintained garden with flowers and shrubs.

A pool area with lounge chairs and umbrellas, surrounded by stone walls and greenery, with a view of distant hills.

Il Defizio

Gambassi Terme

10/10 Exceptional

Courtney

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 buffet setup with various food items and beverages, wooden crates, and a stone wall background.

A well-lit outdoor area with a stone building, tall trees, and a pathway leading to the entrance.

Tenuta Sovestro - Agriturismo e Winery

San Gimignano

10/10 Exceptional

Jennifer Olson

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 landscaped garden with a fountain, stone pathways, and a view of distant hills during twilight.

A restaurant with multiple tables and chairs, a wall decorated with plates, and a buffet area with food items.

il Casale del Cotone

San Gimignano

10/10 Exceptional

Salvatore

A swimming pool with lounge chairs and a view of a hill with buildings.

A cozy dining area with a wooden table and chairs, a sofa, and a fireplace.

An aerial view of a vineyard with rows of grapevines, a large building with a swimming pool, and a distant hilltop town.

A view from a window overlooking a rural landscape with rolling hills and vineyards.

Agriturismo Il Casolare di Bucciano

San Gimignano

10/10 Exceptional

We stayed here as part of our tour through Tuscany. Although we wanted to visit San Gimignano, we knew that it would be packed with tourists and bus tours, so we wanted to find a place close enough to visit the town, but away from the hectic crowds. Agriturismo Il Casolare di Bucciano perfectly suited those needs; we had a lovely view of San Gimignano from the grounds. Our GPS had trouble finding this place, because it is a rural address, but the personal connection always seems to work - a...

Jennifer

Frequently Asked Questions

What accommodations do travelers like in Montecastelli?

Guests like Castello di Casole, A Belmond Hotel, Tuscany.

Can I book a refundable accommodation in Montecastelli?

If you're looking for the flexibility to change your plans to Montecastelli, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Montecastelli if I want a vacation rental instead of a hotel?

If you're looking for a good alternative to a hotel, review our selection of 16 vacation homes. In addition, you can choose from 16 apartments.

What will the weather in Montecastelli be like during my visit?

August and July are typically the warmest months in Montecastelli when the average temp is 72°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 Montecastelli accommodation with Hotels.com?

There are lots of reasons to book your Montecastelli 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.