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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Montecastelli holiday rentals

Comfort Studio, Hill View | Outdoor dining

Belvedere Nada

Belvedere Nada
San Rocco A Pilli
The price is 5.201.595 ₫
5.721.755 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Belvedere Nada
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.936.306 ₫
5.579.522 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Antico Borgo il Cardino
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 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 4.405.959 ₫
6.970.662 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Borgo Il Poggiaccio
Seasonal outdoor pool, pool loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (5 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is 5.253.372 ₫
5.868.461 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Residence Arianna
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is 2.596.760 ₫
2.916.270 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Palazzo Pacini
Premium bedding, down duvets, pillow-top beds, desk

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.033.314 ₫
2.625.567 ₫ total
includes taxes & fees
25 Aug - 26 Aug
Tuscasì Aparthotel
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 1.321.788 ₫
1.513.801 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Sportland
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (25 reviews)
"A wonderful stay. "
United States
Sally
The price is 3.524.767 ₫
3.966.994 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Casa di Campagna in Toscana
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is 4.954.256 ₫
5.539.433 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Villa Montecastello
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 3.169.356 ₫
3.486.322 ₫ total
includes taxes & fees
5 Aug - 6 Aug
Residence Il Paradiso
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is 6.731.327 ₫
7.464.294 ₫ total
includes taxes & fees
19 Aug - 20 Aug
Riserva di Fizzano Residence
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 2.808.401 ₫
3.986.751 ₫ total
includes taxes & fees
8 Aug - 9 Aug
Palazzo al Torrione 2
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 3.139.762 ₫
3.573.406 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Il Pozzo di Sant'Andrea
Daily self-service breakfast for a fee

Beatabb

Beatabb
Guardistallo
9.2 out of 10, Wonderful, (12 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 2.714.071 ₫
2.985.478 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Beatabb
Front of property – evening/night

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 3.634.916 ₫
4.147.992 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Residence Borgo San Lorenzo a Linari
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, (64 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 3.798.100 ₫
4.327.494 ₫ total
includes taxes & fees
30 Jul - 31 Jul
B&B Palazzo Tortoli
Outdoor pool, pool loungers

Hotel Campo Di Carlo

Hotel Campo Di Carlo
Sassetta
9.8 out of 10, Exceptional, (6 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 3.016.722 ₫
3.378.229 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Hotel Campo Di Carlo
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is 3.190.843 ₫
3.659.512 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Casa Vacanze Le Case
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (344 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.399.044 ₫
2.758.617 ₫ total
includes taxes & fees
4 Aug - 5 Aug
ApartHotel Anghel
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (53 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is 2.593.206 ₫
2.972.254 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Fullino Nero
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

Hotel Casolare Le Terre Rosse

Hotel Casolare Le Terre Rosse

10/10 Excellent
"Très belle hôtel bien situé pour visiter les villages des environs si vous aimez voir les paysages toscans"
Martin 2-night trip
Posted 3 hours ago
Hotel Casolare Le Terre Rosse

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 16 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.