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Our top choices for Montemassi hotels

Agriturismo Giù al Pozzo

Agriturismo Giù al Pozzo
Grosseto
9.4 out of 10, Exceptional, (3)
"Schöne Zimmer, super Essen, nette Gastgeber"
Germany
Helmut
$86 nightly
The price is $95
Dec 28 - Dec 29
Total with taxes and fees
Agriturismo Giù al Pozzo

Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (30)
"Great place to stay. Very clean, close to town, great breakfast. "
Canada
Jose Pedro
$61 nightly
The price is $68
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fattoria Pian di Rocca

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (1)
"Everything about this place is perfect, highly recommend."
United States
Ian
$90 nightly
The price is $99
Jan 12 - Jan 13, 2026
Total with taxes and fees
Historic Farmhouse Casa del Chiodo

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.4 out of 10, Exceptional, (16)
"Ras"
France
jean
$63 nightly
The price is $70
Jan 6 - Jan 7, 2026
Total with taxes and fees
B&B da Nada Locanda Toscana

Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.8 out of 10, Excellent, (235)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
$82 nightly
The price is $91
Jan 12 - Jan 13, 2026
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel

Grand Hotel Bastiani

Grand Hotel Bastiani
4.0 star property
Grosseto
8.6 out of 10, Excellent, (223)
"Excellent hotel with a premium location"
United States
Pedro
$91 nightly
The price is $100
Dec 29 - Dec 30
Total with taxes and fees
Grand Hotel Bastiani

Granduca

Granduca
4.0 star property
Grosseto
8.0 out of 10, Very Good, (102)
"Clean room, great parking and friendly staff"
Canada
Georges
$85 nightly
The price is $93
Dec 28 - Dec 29
Total with taxes and fees
Granduca

Hotel I Crespi

Hotel I Crespi
3.0 star property
Grosseto
8.8 out of 10, Excellent, (98)
"Breakfast was great!"
United States
john
$101 nightly
The price is $111
Jan 7 - Jan 8, 2026
Total with taxes and fees
Hotel I Crespi

Hotel Airone

Hotel Airone
4.0 star property
Grosseto
8.4 out of 10, Very Good, (109)
"Loved the hot tub area! "
United States
Robert
$122 nightly
The price is $134
Dec 28 - Dec 29
Total with taxes and fees
Hotel Airone

Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
4.0 star property
Gavorrano
8.8 out of 10, Excellent, (128)
"Was good enough. Sauna is a unique feature in Italian retreats. However, no freezers or teapots in rooms"
United States
Assan
Montebelli Agriturismo & Country Hotel

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.4 out of 10, Exceptional, (28)
"pretty setting"
Canada
ed
$175 nightly
The price is $193
Jan 5 - Jan 6, 2026
Total with taxes and fees
Valdonica Winery & Vineyard Residence

Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
9.6 out of 10, Exceptional, (40)
"The pool was great, the room was a great size and clean and breakfast was good."
Canada
Tresa
Antico Casale L'Impostino

Riva Toscana Golf Resort & SPA

Riva Toscana Golf Resort & SPA
4.0 star property
Follonica
9.2 out of 10, Wonderful, (20)
"We stayed out of the main building the golf condition wasn’t good reason why we didn’t play breakfast needs Coffee they offer expresso but not regular coffee , Bruno is great. Good location "
United States
Patricia
$169 nightly
The price is $186
Dec 28 - Dec 29
Total with taxes and fees
Riva Toscana Golf Resort & SPA

Agriturismo La Rombaia

Agriturismo La Rombaia
Castiglione della Pescaia
10.0 out of 10, Exceptional, (8)
"The property was lovely. The owners were amazing and went out of their way to assist with a lost bag issue. Even driving into Grosetto to help. A delightful stay!"
Canada
Julia
Agriturismo La Rombaia

Agriturismo Le Giuncaine

Agriturismo Le Giuncaine
Castiglione della Pescaia
$115 nightly
The price is $127
Jan 6 - Jan 7, 2026
Total with taxes and fees
Agriturismo Le Giuncaine

Locanda nel Cassero

Locanda nel Cassero
Civitella Paganico
9.6 out of 10, Exceptional, (5)
"Locanda confortevole e accogliente gentilezza e grande disponibilità "
Italy
Edoardo
$90 nightly
The price is $100
Jan 22 - Jan 23, 2026
Total with taxes and fees
Locanda nel Cassero

Hotel Nuova Grosseto

Hotel Nuova Grosseto
3.0 star property
Grosseto
8.6 out of 10, Excellent, (274)
"Great staff, Friendly and very clean. Great pool be wonderful for children too."
United States
Mark
Hotel Nuova Grosseto

Agriturismo San Galgano

Agriturismo San Galgano
Chiusdino
9.0 out of 10, Wonderful, (43)
"Absolutely amazing. Even the morning was cloudy and overwhelmed with fogs, the view was spectacular with view of 'Abbaye de San Galgano'. The breakfast buffet was also more than delicious. Specifically, the salamis were cut from the staffs, not those bought from manufactured products, which also tasted great. The person who helped our check-in and -out was the only person fluent in English, but you can conversate with other staffs with no problem using your body language, don't worry about this....
Ireland
Siwoo
$103 nightly
The price is $117
Jan 3 - Jan 4, 2026
Total with taxes and fees
Agriturismo San Galgano

Casa in Maremma Tuscany Village

Casa in Maremma Tuscany Village
3.0 star property
Scarlino
8.6 out of 10, Excellent, (76)
"Für Hundehalter sehr empfehlenswert"
Switzerland
Johnny
Casa in Maremma Tuscany Village

Agriturismo il vecchio imposto

Agriturismo il vecchio imposto
Massa Marittima
10.0 out of 10, Exceptional, (1)
"Sehr schön gelegen mit See in der Nähe. Die Ausstattung ist vollständig und der Garten/ die Terasse sind super. "
Germany
Louisa
$92 nightly
The price is $102
Jan 1 - Jan 2, 2026
Total with taxes and fees
Agriturismo il vecchio imposto
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Top Montemassi Hotel Reviews

More cheap stays in Montemassi

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 can I save on a Montemassi hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Montemassi hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $68 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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