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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castellina in Chianti holiday rentals

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

1. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ₹10,764
₹12,469 total
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Squarcialupi
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

2. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is ₹12,004
₹13,624 total
includes taxes & fees
12 Nov - 13 Nov
Agriturismo La Ferrozzola
A two-story house with a patio area, potted plants, and outdoor furniture.

3. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ₹13,590
₹15,368 total
includes taxes & fees
14 Nov - 15 Nov
La Locanda di Pietracupa
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

4. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is ₹24,348
₹27,202 total
includes taxes & fees
13 Nov - 14 Nov
Terre di Baccio
A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

5. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (225 reviews)
"Very nice hotel with wonderful staff. Very accommodating. Would highly recommend."
United States
Anthony
The price is ₹11,379
₹12,937 total
includes taxes & fees
13 Nov - 14 Nov
Il Battistero Siena - Residenza d'Epoca
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

6. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (62 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is ₹9,132
₹10,465 total
includes taxes & fees
12 Nov - 13 Nov
Guild Living Siena Senior Resort & Residence
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

7. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is ₹6,895
₹8,004 total
includes taxes & fees
15 Nov - 16 Nov
B&B Il Corso
A table set with breakfast items on a balcony overlooking a historic town.

8. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (136 reviews)
"We had a great stay!"
United States
Suelina
The price is ₹13,656
₹15,443 total
includes taxes & fees
26 Nov - 27 Nov
Residenza d'Epoca Palazzo Borghesi
A table with two wine glasses, a bottle, and a book.

9. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is ₹6,227
₹7,272 total
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
A historic building with a clock tower, arched windows, and a shop selling souvenirs.

10. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is ₹14,504
₹16,376 total
includes taxes & fees
12 Nov - 13 Nov
PALAZZO DEL PAPA
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (497 reviews)
"The room was modern and clean. Enjoyed the breakfast."
Australia
John
The price is ₹9,177
₹10,515 total
includes taxes & fees
12 Nov - 13 Nov
Siena Vip
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

12. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (77 reviews)
"Breakfast was good and host was great to talk with."
United States
Leslie
The price is ₹9,540
₹10,914 total
includes taxes & fees
12 Nov - 13 Nov
B&B Palazzo del Magnifico
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

13. Palazzo Alfieri Residenza d’epoca - Place of Charme

Palazzo Alfieri Residenza d’epoca - Place of Charme
Historic Centre of Florence
9.2 out of 10, Wonderful, (874 reviews)
"This is an excellent hotel very near the historic area. They offer a wonderful breakfast."
United States
robert
The price is ₹15,691
₹18,728 total
includes taxes & fees
10 Dec - 11 Dec
Palazzo Alfieri Residenza d’epoca - Place of Charme
A stone building with a patio area featuring a table and chairs under a large umbrella.

14. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is ₹8,485
₹9,650 total
includes taxes & fees
26 Nov - 27 Nov
Relais Villa Olmo - Place of Charme
An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is ₹14,968
₹16,884 total
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
A bottle of wine, two glasses, and a decorative tray on a table by a window with a view of buildings.

16. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (86 reviews)
"Excellent place to stay!"
United States
Jessica
The price is ₹7,534
₹8,707 total
includes taxes & fees
30 Nov - 1 Dec
Regis Condo
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

17. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (356 reviews)
"The staff were very friendly and helpful. I would recommend this hotel to any traveler"
United States
clifford
The price is ₹5,892
₹6,902 total
includes taxes & fees
30 Nov - 1 Dec
ApartHotel Anghel
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.

18. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (34 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ₹6,114
₹8,089 total
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A courtyard with a large building featuring arched windows and a tower. There is a parking lot with several cars.

19. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (107 reviews)
"This B and B is great. In the centre of everything."
Canada
Sandra
The price is ₹6,191
₹8,159 total
includes taxes & fees
17 Nov - 18 Nov
Al Mercato B&B
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

20. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,200 reviews)
"We had a good stay! It’s a great location"
Canada
Heather
The price is ₹8,539
₹10,868 total
includes taxes & fees
30 Nov - 1 Dec
Palazzo Mannaioni Suites
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 Castellina in Chianti Hotel Reviews

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
Castello La Leccia

Castello La Leccia

Castello La Leccia
Castellina in Chianti

10/10 Excellent

Fantastic hotel with stunning views of the Tuscan countryside.
United Kingdom
Iain
Reviewed April 29, 2026
Castello La Leccia

Find out more about Castellina in Chianti

Holiday Rentals in Castellina in Chianti

Search for holiday rentals in Castellina in Chianti on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Castellina in Chianti using one of the methods below:

  • View our selection of featured holiday rentals in Castellina in Chianti
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Look no further and take a look at our great range of rental properties in Castellina in Chianti!

Frequently Asked Questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Castellina in Chianti speak positively about the countryside and wineries in this destination. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside Castellina in Chianti is located near the airport, and has a garden, a library and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Castellina in Chianti?

With 31 Expedia holiday rentals, you're guaranteed to find just the right place for your Castellina in Chianti stay.

What’s there to see and do in Castellina in Chianti?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Castellina Fortress are other places worth a visit.

What’s a holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.