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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Montecastelli holiday rentals

Romantic Double Room, 1 Bedroom, Non Smoking | View from room

1. 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 3.817.031 ₫
4.349.065 ₫ total
includes taxes & fees
11 Oct - 12 Oct
B&B Palazzo Tortoli
Food court

2. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is 2.238.991 ₫
4.597.585 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Borgo Il Poggiaccio
Family Apartment, 5 Bedrooms, Garden View, Garden Area (10 people) | Terrace/patio

3. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is 8.696.986 ₫
9.717.144 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Borgo al Cerro
Exterior

4. 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 2.736.837 ₫
3.130.785 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Il Pozzo di Sant'Andrea
Casa Alberi - Albergo Diffuso Volterra | Desk, laptop workspace, free WiFi, bed sheets

5. AlbergoDiffusoVolterra

AlbergoDiffusoVolterra
Volterra
8.6 out of 10, Excellent, (19 reviews)
"Lovely stay at a little gem in Volterra. Enrico the owner has created a great concept with different apartments around the city and the restaurant is serving delicious local plant based food. Don’t miss the cheesecake ❤️"
Sweden
Mia
The price is 3.204.928 ₫
4.547.669 ₫ total
includes taxes & fees
18 Sept - 19 Sept
AlbergoDiffusoVolterra
Outdoor pool, pool loungers

6. 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 3.272.338 ₫
3.659.755 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Hotel Campo Di Carlo
Terrace/patio

7. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is 3.168.422 ₫
3.575.462 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Casa di Campagna in Toscana
Exterior

8. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.058.926 ₫
4.615.150 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Antico Borgo il Cardino
Terrace/patio

9. 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 4.008.743 ₫
4.469.749 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Palazzo Pacini
Reception

10. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is 1.196.556 ₫
1.376.394 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Sportland
Seasonal outdoor pool, pool loungers

11. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 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 3.566.935 ₫
4.013.826 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Residence Arianna
Apartment, 1 Bedroom, Ground Floor (Garden) | Exterior

12. 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 1.960.476 ₫
2.156.674 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Residence Il Paradiso
Premium bedding, down duvets, pillow-top beds, desk

13. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 2.155.741 ₫
2.461.513 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Tuscasì Aparthotel
Balcony

14. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is 2.822.399 ₫
4.006.623 ₫ total
includes taxes & fees
10 Oct - 11 Oct
Palazzo al Torrione 2
Lobby lounge

15. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (345 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.898.073 ₫
3.308.144 ₫ total
includes taxes & fees
6 Oct - 7 Oct
ApartHotel Anghel
Aerial view

16. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is 5.475.860 ₫
6.083.578 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Riserva di Fizzano Residence
Front of property – evening/night

17. Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (99 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is 3.280.037 ₫
3.758.266 ₫ total
includes taxes & fees
26 Sept - 27 Sept
Residence Borgo San Lorenzo a Linari
Exterior

18. 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 2.186.709 ₫
2.525.554 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Villa le Camelie Siena
Superior Mobile Home | Terrace/patio

19. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is 1.352.975 ₫
1.578.470 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Camping Boschetto Di Piemma
Food court

20. 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 4.550.808 ₫
5.096.207 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Antico Borgo Poggiarello
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 Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 1 hour ago
Hotel Italia

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 Palazzo dei Priori.

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.