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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Our top choices for Montecastelli holiday rentals

Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is 2.939.584 ₫
3.355.540 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Il Pozzo di Sant'Andrea
Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

Residence Il Paradiso

Residence Il Paradiso
3.0 star property
Guardistallo
8.4 out of 10, Very good, (26 reviews)
"Absolutely beautiful property among the pine trees. Nice little restaurant, ideal pools and play area for little kids. Location is perfect for exploring the region. Great beaches only 10-15 minutes away. The apartment was very clean and everything necessary for our stay was available. Would gladly visit again. Thank you Il Paradiso!"
Germany
Jason
The price is 2.080.611 ₫
2.288.672 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Residence Il Paradiso
Romantic Double Room, 1 Bedroom, Non Smoking | View from room

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (63 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is 3.872.033 ₫
4.411.733 ₫ total
includes taxes & fees
14 Jun - 15 Jun
B&B Palazzo Tortoli
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.021.922 ₫
2.620.605 ₫ total
includes taxes & fees
17 Jun - 18 Jun
Tuscasì Aparthotel
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is 4.518.342 ₫
5.031.175 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Palazzo Pacini
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is 4.154.845 ₫
6.735.784 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Borgo Il Poggiaccio
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (83 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.422.408 ₫
5.017.146 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Antico Borgo il Cardino
Outdoor pool, pool loungers

Hotel Campo Di Carlo

Hotel Campo Di Carlo
Sassetta
9.6 out of 10, Exceptional, (5 reviews)
"Ci siamo fermati una Notte! Personale gentilissimo tutto perfetto ci ritorneremo fermandoci per più giorni e provare la piscina e le Terme nelle vicinanze"
Italy
antonio
The price is 2.126.637 ₫
2.400.300 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Hotel Campo Di Carlo
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is 3.368.794 ₫
3.797.171 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Casa di Campagna in Toscana
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (339 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.322.221 ₫
2.676.440 ₫ total
includes taxes & fees
13 Jul - 14 Jul
ApartHotel Anghel
Exterior

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 2.754.924 ₫
3.091.416 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Country House il Ciliegio
Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is 1.347.517 ₫
1.543.268 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Sportland
Daily self-service breakfast for a fee

Beatabb

Beatabb
Guardistallo
9.2 out of 10, Wonderful, (9 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
The price is 2.515.366 ₫
2.766.902 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Beatabb
Front of property

Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is 5.726.948 ₫
6.452.140 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Residence Borgo San Lorenzo a Linari
Exterior

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is 2.495.458 ₫
2.866.940 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Villa le Camelie Siena
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is 2.863.069 ₫
4.064.357 ₫ total
includes taxes & fees
16 Jun - 17 Jun
Palazzo al Torrione 2
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is 4.286.209 ₫
4.806.328 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Antico Borgo Poggiarello
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is 3.029.142 ₫
3.484.553 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Casa Vacanze Le Case
Superior Mobile Home | Terrace/patio

Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is 1.621.956 ₫
1.875.711 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Camping Boschetto Di Piemma
Apartment, 2 Bedrooms, Hill View | Terrace/patio

Antica Fonte Residenza di Siena

Antica Fonte Residenza di Siena
Siena
6.0 out of 10, (2 reviews)
"Not very good hosts. They don’t speak English and they don’t help accomodate guests for issues out of their control. I would stay away very poor customer service "
Australia
Geoffrey
The price is 2.633.925 ₫
3.019.436 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Antica Fonte Residenza di Siena
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 Montecastelli Hotel Reviews

Cappuccina Country Resort

Cappuccina Country Resort

10/10 Excellent
"Hotel and rooms were spotless.There is a nice pool to cool off on those hot days.Overall a great stay"
tony 1-night trip
Posted 1 day ago
Cappuccina Country Resort

Frequently asked questions

Are there holiday rentals in Montecastelli?

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

How many holiday rentals will I find in Montecastelli?

Expedia has 15 holiday rentals for your stay in Montecastelli.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Terre di Vini, or get out into nature at a spot like Alta Val d'Elsa River Park. In the wider area, you’ll find Medici Fortress and Etruscan Museum.

What are holiday rentals like in Montecastelli?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Montecastelli. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling 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 an attractive choice for a family getaway.