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Montecastelli Vacation Rentals

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Check prices for these dates

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

Our top choices for Montecastelli vacation rentals

An interior with stone walls, wooden doors, and a bar area with stools and bottles.

1. 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
$183 nightly
The price is $207
Oct 14 - Oct 15
Total with taxes and fees
Borgo Il Poggiaccio
Outdoor pool

2. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
$135 nightly
The price is $152
Oct 15 - Oct 16
Total with taxes and fees
Residence Arianna
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

3. Nido con vista

Nido con vista
Radicondoli
$135 nightly
The price is $148
Nov 1 - Nov 2
Total with taxes and fees
Nido con vista
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

4. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$72 nightly
The price is $83
Nov 2 - Nov 3
Total with taxes and fees
Tuscasì Aparthotel
A garden with a stone pathway, wooden benches, and various potted plants.

5. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
$129 nightly
The price is $147
Oct 25 - Oct 26
Total with taxes and fees
Antico Borgo il Cardino
A stone courtyard with a bench, potted plants, and a building in the background.

6. 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
$98 nightly
The price is $111
Oct 30 - Oct 31
Total with taxes and fees
Casa di Campagna in Toscana
A stone building with a tiled roof, a brick pathway, and a small grassy area.

7. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
$178 nightly
The price is $198
Oct 11 - Oct 12
Total with taxes and fees
Le Mascie Country House
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

8. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$133 nightly
The price is $149
Nov 6 - Nov 7
Total with taxes and fees
Palazzo Pacini
A balcony with potted plants and a view of rolling hills and mountains.

9. A Nest with a View - A Romantic Retreat Within the City Walls

A Nest with a View - A Romantic Retreat Within the City Walls
Radicondoli
$159 nightly
The price is $159
Nov 1 - Nov 2
Total with taxes and fees
A Nest with a View - A Romantic Retreat Within the City Walls
A stone building with outdoor seating and a view of the countryside.

10. 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
$152 nightly
The price is $170
Oct 21 - Oct 22
Total with taxes and fees
Antico Borgo Poggiarello
A stone building with a flat roof, multiple windows, and a small porch area.

11. Podere Cagnesi: Relaxation in nature

Podere Cagnesi: Relaxation in nature
Podere Cagnesi
$203 nightly
The price is $229
Oct 20 - Oct 21
Total with taxes and fees
Podere Cagnesi: Relaxation in nature
A building with a stucco exterior, multiple windows, and a tiled roof.

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
$73 nightly
The price is $81
Oct 13 - Oct 14
Total with taxes and fees
Residence Il Paradiso
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

13. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (90 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$46 nightly
The price is $54
Oct 7 - Oct 8
Total with taxes and fees
Camping Boschetto Di Piemma
A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

14. Beatabb

Beatabb
Guardistallo
9.4 out of 10, Exceptional, (19 reviews)
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
$78 nightly
The price is $86
Nov 5 - Nov 6
Total with taxes and fees
Beatabb
A cozy room with a wooden ceiling, a dining table set with plates, cups, and a vase, and a sofa with a book on it.

15. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
Località Gerfalco Montieri
Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access
A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

16. 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
$153 nightly
The price is $170
Oct 13 - Oct 14
Total with taxes and fees
AlbergoDiffusoVolterra
An open wooden door leading to an outdoor patio with a table and chairs.

17. 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
$131 nightly
The price is $149
Oct 30 - Oct 31
Total with taxes and fees
Palazzo al Torrione 2
A reception desk with the word "SPORTLAND" prominently displayed.

18. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
$44 nightly
The price is $50
Oct 11 - Oct 12
Total with taxes and fees
Sportland
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

19. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
$92 nightly
The price is $107
Nov 2 - Nov 3
Total with taxes and fees
Casa Vacanze Le Case
Room

20. Apartment 'Timignano in Agriturismo' with Mountain View, Pool among the Hills

Apartment 'Timignano in Agriturismo' with Mountain View, Pool among the Hills
Monteguidi
$392 nightly
The price is $394
Nov 2 - Nov 3
Total with taxes and fees
Apartment 'Timignano in Agriturismo' with Mountain View, Pool among the Hills
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 Sovestro

Hotel Sovestro

10/10 Excellent
"We were looking for a Tuscan experience and this hotel more than met our expectations. They had an excellent restaurant on site for breakfast and dinner. The pool was large and nice to use after a day of visiting. Hotel is close to San Gimignano which is a must see town, We used the hotel shuttle to get to the town since it was an uphill walk and walked back. The sights were quite spectacular. We had a wine tasting of their vineyards wines which was also very nice. Can not say enough about how much we enjoyed our stay."
Franco 4-night trip
Posted 1 day ago
Hotel Sovestro

Find out more about Montecastelli

Everything you need to know about Montecastelli vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montecastelli vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montecastelli vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecastelli vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecastelli. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montecastelli in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $54 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montecastelli rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montecastelli vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montecastelli. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Montecastelli?

Yes, we offer vacation rentals close to top points of interest in Montecastelli, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Montecastelli has to offer?

Villa with large garden in the Chianti hills: This vacation home rental outside of Montecastelli is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Montecastelli?

Expedia has 16 vacation 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 Sentierelsa Trail. In the larger area, you’ll find Medici Fortress and Porta all'Arco.

What are vacation rentals like in Montecastelli?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Montecastelli. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.