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Villas in Montemassi

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Montemassi villas

A historic stone building with multiple windows and a courtyard.

1. Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
3.0 star property
Roccastrada
9.6 out of 10, Exceptional, (10 reviews)
"Great place , welcoming owner and staff . Town is a little gem "
United States
Alice
$105 nightly
The price is $118
Sep 27 - Sep 28
Total with taxes and fees
Agriturismo Tenuta di Montemassi La Fattoria
A swimming pool with a view of a valley and mountains.

2. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (44 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
$148 nightly
The price is $165
Oct 11 - Oct 12
Total with taxes and fees
Valdonica Winery & Vineyard Residence
A balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.

3. Tenuta il Sassone - Wine & Food

Tenuta il Sassone - Wine & Food
Gavorrano
9.8 out of 10, Exceptional, (11 reviews)
"The property was by far much better than expected, the staff and the owner of the hotel treated us as though we were part of their family. It was one of the best hotels we have stayed in anywhere in the world."
United Kingdom
Christine
$107 nightly
The price is $126
Oct 6 - Oct 7
Total with taxes and fees
Tenuta il Sassone - Wine & Food
A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.

4. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
$110 nightly
The price is $121
Oct 10 - Oct 11
Total with taxes and fees
Le Vie del Mare Camere
A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

5. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
4.0 star property
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
"Everything was excellent, the room was stunning and quiet except for the birds, which was bliss. The restaurant was also great food, we had a great sleep and breakfast, I only wish we could have stayed longer."
Australia
Gillian
$87 nightly
The price is $99
Oct 15 - Oct 16
Total with taxes and fees
La Melosa Resort & Spa - Adults Only
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.

6. 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
$618 nightly
The price is $684
Oct 15 - Oct 16
Total with taxes and fees
Conti di San Bonifacio Wine Resort
A group of people dining at a table with a view of a valley and mountains.

7. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
$183 nightly
The price is $204
Sep 23 - Sep 24
Total with taxes and fees
Valdonica Winery - Chill in Nature Lodge
A pool area with lounge chairs and umbrellas, surrounded by greenery and hills.

8. Tenuta Casteani

Tenuta Casteani
Gavorrano
8.8 out of 10, Excellent, (12 reviews)
"Great venue, amazing views, very friendly staff. Would love to go back!"
United Kingdom
Andrew
$117 nightly
The price is $133
Sep 29 - Sep 30
Total with taxes and fees
Tenuta Casteani
An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

9. Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
4.0 star property
Gavorrano
8.8 out of 10, Excellent, (134 reviews)
"Toscane immersion spa hotel"
Canada
Jean-Olivier
$97 nightly
The price is $114
Oct 23 - Oct 24
Total with taxes and fees
Montebelli Agriturismo & Country Hotel
An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

10. 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
$85 nightly
The price is $99
Oct 18 - Oct 19
Total with taxes and fees
Agriturismo Giù al Pozzo
A pool with lounge chairs and a sunset view.

11. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (263 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
$86 nightly
The price is $95
Sep 23 - Sep 24
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
A clear pool with visible mineral deposits, a pebble beach, and a mountainous landscape in the background.

12. VIN Hotel - La Meridiana

VIN Hotel - La Meridiana
Montieri
9.4 out of 10, Exceptional, (22 reviews)
"Great hospitality!!!!"
United States
Anastasia
$130 nightly
The price is $143
Sep 28 - Sep 29
Total with taxes and fees
VIN Hotel - La Meridiana
A covered courtyard with stone columns, a brick floor, and a grassy area.

13. Hotel Girifalco - Nature & Relax

Hotel Girifalco - Nature & Relax
Massa Marittima
9.2 out of 10, Wonderful, (14 reviews)
"Charming hotel. Excellent breakfast. I would recommend it"
Canada
Lucy
$47 nightly
The price is $64
Oct 23 - Oct 24
Total with taxes and fees
Hotel Girifalco - Nature & Relax
An outdoor dining area with a wooden pergola, white tablecloths, and chairs.

14. 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)
"Very nice private beach. Rooms - we had a bungalow- are totally ok, yet need a refresh/update. Breakfast was very good, friendly stuff, non problem at all to stay longer even though bf ended at 10am. We enjoyed our time at Il Pelagone- many thanks!"
United Kingdom
Matthias
$152 nightly
The price is $174
Oct 10 - Oct 11
Total with taxes and fees
Il Pelagone Hotel & Golf Resort Toscana
A large, multi-story building surrounded by lush greenery and fields.

15. L'Andana

L'Andana
5.0 star property
Castiglione della Pescaia
9.4 out of 10, Exceptional, (97 reviews)
"Clean room"
United States
Aleksandr
$433 nightly
The price is $488
Oct 4 - Oct 5
Total with taxes and fees
L'Andana
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

16. Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Great for families, convenient parking and facilities, very tranquil."
United States
Ciarán
$56 nightly
The price is $69
Sep 30 - Oct 1
Total with taxes and fees
Podere Cascatelle & Agriletizia
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.

17. Borgo Santo Pietro

Borgo Santo Pietro
5.0 star property
Chiusdino
9.6 out of 10, Exceptional, (67 reviews)
"Staff were incredible and the place was beautiful!! We will be back"
United States
Rachel
$1,147 nightly
The price is $1,273
Sep 30 - Oct 1
Total with taxes and fees
Borgo Santo Pietro
A couple standing in a spacious room with a large window overlooking a vineyard.

18. Hotel L'Approdo

Hotel L'Approdo
4.0 star property
Castiglione della Pescaia
8.4 out of 10, Very good, (204 reviews)
"Clean rooms excellent location"
United States
Ernesto
$89 nightly
The price is $103
Oct 23 - Oct 24
Total with taxes and fees
Hotel L'Approdo
A rural landscape with rolling hills, a large stone building, and a swimming pool surrounded by greenery.

19. Casale Vigna Carbona

Casale Vigna Carbona
Gavorrano
10.0 out of 10, Exceptional, (1 review)
"Cosa scrivere su questo magnifico angolo della maremma. Posto stupendo immerso nella natura, pulizia delle camere impeccabile così come la piscina se poi ci metti anche la cordialità di Luigi e di sua figlia Agnese padroni di casa impeccabili direi che non potevo scegliere posto migliore. Bravi, bravi , bravi "
Italy
Gennaro
$125 nightly
The price is $142
Sep 26 - Sep 27
Total with taxes and fees
Casale Vigna Carbona

20. Riva del Sole Resort & SPA

Riva del Sole Resort & SPA
4.0 star property
Castiglione della Pescaia
9.2 out of 10, Wonderful, (52 reviews)
"The property was a bit older in style but the staff was nice and it was clean"
United States
Antoneta
$236 nightly
The price is $266
Oct 12 - Oct 13
Total with taxes and fees
Riva del Sole Resort & SPA
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.
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Top Montemassi Hotel Reviews

Hotel La Pineta

Hotel La Pineta

8/10 Good
"Excellent breakfast and dinner at same restaurant with beautiful patio. Nice lunch cafe in front also for aperitif. Close to street though. Very friendly staff. Rooms are a bit cold with no decor. Rooms close to stairs and elevator are noisy. We had room 112. Heard everything from the hallways which was annoying at night. Room had a very strong disinfectant odor. Overall highly recommend the hotel."
dirk 1-night trip
Posted 3 hours ago
Hotel La Pineta

Find out more about Montemassi

Montemassi Villas information

Number of reviews
576
Accommodation
213 Villas
Lowest Price
$64
Highest Price
$684

Frequently asked questions

How much do villas in Montemassi cost?
You'll pay between $64 and $684 per night for a villa in Montemassi. Whatever your budget, the perfect getaway is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Montemassi?
Use up your vacation days and pick from 213 villas in Montemassi. For a family adventure, a getaway with your besties and everything in between, Expedia can help you find the perfect place in just a few clicks.
Why book your villa in Montemassi with Expedia?
Reserving a villa in Montemassi is as easy as working out your travel dates and picking the option that meets your requirements. Searching for something inexpensive or upscale, or a property that also comes with a pool? Use Expedia's search filters to narrow your results and find your ideal match.
How can I find cheap villas in Montemassi?
The simplest way to score cheap villas in Montemassi is with Expedia's useful filter tool. Tailor your search results by budget, amenities and star rating to find unbeatable deals in only a couple of clicks.

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