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Nov 13 - Nov 15
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Nov 20 - Nov 22

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Our top choices for Montemassi hotels

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

1. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
"After debating between many Tuscan vineyards/B&Bs to stay at, I am so glad we picked this one. The venue was beautiful, the room was nice and clean (with AC), and they had a gorgeous remote pool overlooking the vineyard. The people working were all incredibly kind and accommodating and went above and beyond to make our stay memorable, in addition to the owner. We enjoyed a wine tour/tasting and a cooking class, and had dinner at their restaurant that was one of our best meals in Italy. Our only...
United States
Audrey
$149 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
Valdonica Winery & Vineyard Residence
Point of interest

2. B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (18 reviews)
"Ras"
France
jean
$73 nightly
The price is $82
Nov 11 - Nov 12
Total with taxes and fees
B&B da Nada Locanda Toscana
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

3. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
$110 nightly
The price is $121
Nov 10 - Nov 11
Total with taxes and fees
Le Vie del Mare Camere
A bedroom with a bed, a hanging light fixture, and a view of a patio with a table and chairs.

4. Agriturismo Giù al Pozzo

Agriturismo Giù al Pozzo
Gavorrano
9.6 out of 10, Exceptional, (5 reviews)
"This stay was beautiful! There was pretty countryside and the hotel grounds were very pretty as well."
United States
Micaiah
$75 nightly
The price is $82
Nov 25 - Nov 26
Total with taxes and fees
Agriturismo Giù al Pozzo
A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

5. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (6 reviews)
"Everything about this place is perfect, highly recommend."
United States
Ian
$105 nightly
The price is $118
Nov 10 - Nov 11
Total with taxes and fees
Historic Farmhouse Casa del Chiodo
A bedroom with a wooden headboard, a large bed, a framed picture on the wall, and a sliding glass door leading to an outdoor area.

6. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
$158 nightly
The price is $176
Nov 16 - Nov 17
Total with taxes and fees
Valdonica Winery - Chill in Nature Lodge
A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

7. Conti di San Bonifacio Wine Resort

Conti di San Bonifacio Wine Resort
Gavorrano
9.4 out of 10, Exceptional, (29 reviews)
"Unbelievable beautiful place. We absolutely loved our time there. "
United States
Hannah
$542 nightly
The price is $597
Nov 11 - Nov 12
Total with taxes and fees
Conti di San Bonifacio Wine Resort
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

8. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
$81 nightly
The price is $92
Nov 16 - Nov 17
Total with taxes and fees
Country House il Ciliegio
A swimming pool with a waterfall feature, large windows, and a lounge chair.

9. Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
4.0 star property
Gavorrano
8.6 out of 10, Excellent, (136 reviews)
"Toscane immersion spa hotel"
Canada
Jean-Olivier
$114 nightly
The price is $126
Nov 13 - Nov 14
Total with taxes and fees
Montebelli Agriturismo & Country Hotel
A building with a stone facade and multiple windows.

10. Agriturismo San Galgano

Agriturismo San Galgano
Chiusdino
9.0 out of 10, Wonderful, (45 reviews)
"I loved every moment at the Agriturismo San Galgano. Beautifully restored for modern times, interior decoration appointed with excellent taste. Lovely pond and pool on the property. It is very convenient to have the restaurant on the property. The location is magical right next to the famous Abbey of San Galgano. Looking forward to returning in the near future. Have wonderful memories of my stay."
United Kingdom
Irene
$99 nightly
The price is $113
Nov 13 - Nov 14
Total with taxes and fees
Agriturismo San Galgano
A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

11. Il Pelagone Hotel & Golf Resort Toscana

Il Pelagone Hotel & Golf Resort Toscana
4.0 star property
Gavorrano
8.6 out of 10, Excellent, (25 reviews)
"We had a great time here. Everyone was helpful, golf course was great and rooms worked out well. The breakfast was probably the best of our trek throughout Italy. Loved it here."
United States
Jordan
$122 nightly
The price is $134
Nov 26 - Nov 27
Total with taxes and fees
Il Pelagone Hotel & Golf Resort Toscana
A covered patio area with stone walls, wooden beams, and outdoor furniture.

12. Casale San Galgano

Casale San Galgano
Chiusdino
10.0 out of 10, Exceptional, (24 reviews)
"Staff was great! Made the stay feel like home"
United States
Adam
$113 nightly
The price is $128
Dec 7 - Dec 8
Total with taxes and fees
Casale San Galgano
A pool with lounge chairs and a sunset view.

13. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (267 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
$84 nightly
The price is $92
Nov 10 - Nov 11
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped garden and a building with a tiled roof.

14. Agriturismo Bio Fattoria Casetta

Agriturismo Bio Fattoria Casetta
2.0 star property
Gavorrano
10.0 out of 10, Exceptional, (2 reviews)
"Ottima location il titolare persona squisita pace tranquillità caratterizzano il posto da ritornarci sicuramente"
Italy
Piero
$86 nightly
The price is $95
Nov 10 - Nov 11
Total with taxes and fees
Agriturismo Bio Fattoria Casetta
A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

15. Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
9.4 out of 10, Exceptional, (53 reviews)
"Very nice stay"
United States
Maria
$130 nightly
The price is $143
Nov 11 - Nov 12
Total with taxes and fees
Antico Casale L'Impostino
A modern lobby with a reception desk, a globe, seating area, and large windows.

16. Hotel Nuova Grosseto

Hotel Nuova Grosseto
3.0 star property
Grosseto
8.6 out of 10, Excellent, (295 reviews)
"Breakfast was lovely, cappuccino delicious and the breakfast lady delightful. A little noisy early in the morning being so close the the train station "
Canada
Karen
$78 nightly
The price is $86
Dec 9 - Dec 10
Total with taxes and fees
Hotel Nuova Grosseto
A concrete staircase leading to a flat roof area with a metal railing, a potted cactus, and a bench.

17. Ostello La Miniera

Ostello La Miniera
Massa Marittima
7.4 out of 10, Good, (3 reviews)
$61 nightly
The price is $67
Nov 15 - Nov 16
Total with taxes and fees
Ostello La Miniera
A historic building with a sign reading "LOANDA" and a stone staircase leading to the entrance.

18. Locanda nel Cassero

Locanda nel Cassero
Civitella Paganico
9.4 out of 10, Exceptional, (6 reviews)
"Locanda confortevole e accogliente gentilezza e grande disponibilità "
Italy
Edoardo
$87 nightly
The price is $95
Dec 1 - Dec 2
Total with taxes and fees
Locanda nel Cassero
A two-story house with a stone facade, a balcony, and a gated entrance.

19. Molino Della Volta

Molino Della Volta
2.0 star property
Grosseto
$72 nightly
The price is $79
Dec 8 - Dec 9
Total with taxes and fees
Molino Della Volta
A two-story building with a central courtyard, balconies, and a well-maintained garden with pink flowers.

20. Agriturismo il vecchio imposto

Agriturismo il vecchio imposto
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful backyard and olive orchard super nice covered large table for breakfast. Large rooms good ac no or very few mosquitoes. Would stay here again"
United States
Rollie
$82 nightly
The price is $90
Nov 10 - Nov 11
Total with taxes and fees
Agriturismo il vecchio imposto
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Compare top hotels in Montemassi

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

Valdonica Winery & Vineyard Residence

Roccastrada
View
Point of interest

B&B da Nada Locanda Toscana

Roccastrada
View
A bedroom with a bed, a hanging light fixture, and a view of a patio with a table and chairs.

Agriturismo Giù al Pozzo

Gavorrano
View
A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

Historic Farmhouse Casa del Chiodo

Roccastrada
View
A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

Conti di San Bonifacio Wine Resort

Gavorrano
View
9.2
Wonderful
46 reviews
9.6
Exceptional
18 reviews
9.6
Exceptional
5 reviews
10.0
Exceptional
6 reviews
9.4
Exceptional
29 reviews
$149 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
$73 nightly
The price is $82
Nov 11 - Nov 12
Total with taxes and fees
$75 nightly
The price is $82
Nov 25 - Nov 26
Total with taxes and fees
$105 nightly
The price is $118
Nov 10 - Nov 11
Total with taxes and fees
$542 nightly
The price is $597
Nov 11 - Nov 12
Total with taxes and fees
  • Yes, Breakfast included
  • Yes, Pool
  • Yes, Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • No Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • No Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking

Hotels recommended for families in Montemassi

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46)
$149 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
Valdonica Winery & Vineyard Residence
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Top Montemassi Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Unique property well maintained and quite Serene , great staff"
KEDARNATH 3-night trip
Posted 10 days ago
Castiglion del Bosco, A Rosewood Hotel

More cheap stays in Montemassi

Hotel Massa Vecchia

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR
Get rates
8.6/10 Excellent! (11 reviews)

Hotels in Montemassi with star-rating

Frequently asked questions

What is the best area to stay in Montemassi?
The best area to stay in Montemassi is directly within the village walls of Montemassi itself, or in the immediate countryside surrounding it.

Montemassi is a small, historic hilltop village dominated by its medieval castle ruins. The village consists of a few narrow, winding streets that lead up to the castle, offering elevated views of the surrounding Tuscan landscape. There are a handful of traditional eateries and local shops within the village.

For couples seeking a romantic and tranquil escape, staying within Montemassi offers an intimate experience. You'll enjoy quiet evenings with stunning views and the charm of historic architecture, superb for unwinding and savoring local cuisine.

Travelers looking for a more expansive retreat with easy access to the village will find the countryside just outside Montemassi ideal.
When is the best time to go to Montemassi?
The best times to visit Montemassi are during the spring (April to June) and autumn (September to October) months.

These shoulder seasons offer pleasant weather conditions, ideal for exploring the Tuscan countryside. You'll find comfortable temperatures for outdoor activities like vineyard tours or walks through olive groves. Additionally, these periods avoid the peak summer crowds, allowing for a more serene experience at Montemassi's historic sites and local trattorias.

Couples often find these times superb for a romantic getaway. The spring brings blooming wildflowers and lush green landscapes, while autumn offers the beauty of changing leaves and the excitement of the grape harvest season.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montemassi.
How much is the nightly rate at a Montemassi hotel?
Prices for hotels in Montemassi often vary, but you can find a great deal from $67 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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