Default HTG hotel image

Montemassi Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Montemassi holiday rentals

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

1. 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
The price is S$120
includes taxes & fees
5 Nov - 6 Nov
Country House il Ciliegio
An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

2. 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
Podere Cascatelle & Agriletizia
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

3. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
The price is S$116
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

4. Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (34 reviews)
"We are very happy with everything in this hotel, nice room, comfortable bed, and very good breakfast."
Sweden
Tor
The price is S$119
includes taxes & fees
18 Oct - 19 Oct
Fattoria Pian di Rocca
A person relaxing in a hot tub with a glass of wine.

5. Botrona B&B

Botrona B&B
Scarlino
9.4 out of 10, Exceptional, (26 reviews)
"Amazing B&B! Beautiful, clean, and very classy! Staff is excellent and friendly… breakfast is superb and staff’s hospitality is heart warming. Our stay was very pleasant. Home away from home… surprisingly beautiful grounds with jacuzzi and a sauna available whenever you want! Thank you!"
United States
Anna
The price is S$124
includes taxes & fees
18 Oct - 19 Oct
Botrona B&B
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montemassi Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 14 hours ago
Castiglion del Bosco, A Rosewood Hotel

Frequently asked questions

Are there holiday rentals in Montemassi?

Yes, there are holiday rentals close to the most popular sights in Montemassi, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Montemassi?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Montemassi stay.

What’s there to see and do in Montemassi?

While exploring the area, visit family-friendly sights like Piscina Il Giunco, or get outside and enjoy nature at Lago dell'Accesa. Podere Ristella Vineyards and Winery and Rocca di Frassinello Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Montemassi like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montemassi. Holiday rentals feature extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.