Apartments in Castellina in Chianti for Rent

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Castellina in Chianti apartments

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
$118 nightly
The price is $132
Nov 11 - Nov 12
Total with taxes and fees
Casa Vacanze Squarcialupi
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

2. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Castellina in Chianti
$147 nightly
The price is $151
Dec 1 - Dec 2
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A bedroom with a bed, bedside tables, a dresser, a window with curtains, and wall-mounted lights.

3. Apartment 'La Casa Della Gina' with Wi-Fi

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"We loved our 13 night stay in Castellina in Chianti! The apartment was clean, spacious and well appointed! From the apartment you step out right onto the pedestrian street with shops, bars and restaurants. The grocery is a couple of minutes walking and everyone in town is so friendly! The host is very friendly and helpful and things could not have been better! I highly recommend the apartment for your stay in Tuscany and we were sad to leave!"
United States
Diane W.
$537 nightly
The price is $542
Nov 15 - Nov 16
Total with taxes and fees
Apartment 'La Casa Della Gina' with Wi-Fi
A bottle of wine, two glasses, and a decorative tray on a table by a window with a view of buildings.

4. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (86 reviews)
"Excellent place to stay!"
United States
Jessica
$74 nightly
The price is $86
Nov 19 - Nov 20
Total with taxes and fees
Regis Condo
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

5. 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
$52 nightly
The price is $61
Dec 1 - Dec 2
Total with taxes and fees
ApartHotel Anghel
A historic building with arched windows and a prominent entrance.

6. Casa Ciseri

Casa Ciseri
Siena City Centre
10.0 out of 10, Exceptional, (14 reviews)
"The property is beautiful and location excellent"
United States
Tania
$147 nightly
The price is $166
Dec 10 - Dec 11
Total with taxes and fees
Casa Ciseri
A room with a sofa, a lamp, and a window with a view of an exterior wall.

7. SAN DOMENICO LUXURY APARTMENT

SAN DOMENICO LUXURY APARTMENT
Siena City Centre
10.0 out of 10, Exceptional, (51 reviews)
"we had a great experience! the host met us and helped with parking and provided impeccable service! when we come back to Siena we will rent here again!"
United States
Kyriakos P.
$173 nightly
The price is $173
Nov 18 - Nov 19
Total with taxes and fees
SAN DOMENICO LUXURY APARTMENT
A vineyard with a stone building, a metal gate, and purple plants in the foreground.

8. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
San Gimignano City Centre
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
$238 nightly
The price is $267
Nov 10 - Nov 11
Total with taxes and fees
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
A narrow alleyway with brick walls, wooden barrels, and potted plants.

9. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (44 reviews)
"P. Buonaccorsi is a unique property that is centrally located in San Gimignano. It is well maintained and restored and a very beautiful residence. Senora and Bianca were perfect hosts. The town was perfectly located in Tuscany and within easy day-trips to Florence, Siena, and Massa Marittima."
United States
Glenn
$153 nightly
The price is $158
Nov 11 - Nov 12
Total with taxes and fees
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
Living area

10. Palazzo Lenzi

Palazzo Lenzi
Siena City Centre
9.8 out of 10, Exceptional, (10 reviews)
"Excellent location, incredible view of the Piazza and comfortable beds. Even the pull out bed was surprisingly comfortable. Place was very clean and host met us for check in and helped with any questions. Would definitely stay here again!"
United States
Chadwick
$256 nightly
The price is $287
Dec 10 - Dec 11
Total with taxes and fees
Palazzo Lenzi
A historic stone building with two prominent towers and a central courtyard.

11. Medieval Tower experience with Panoramic Rooftop, San Gimignano

Medieval Tower experience with Panoramic Rooftop, San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (6 reviews)
"This was a perfect stop for the once in a lifetime tour of italy "
United States
mark M.
$488 nightly
The price is $494
Nov 11 - Nov 12
Total with taxes and fees
Medieval Tower experience with Panoramic Rooftop, San Gimignano
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

12. Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (649 reviews)
"Great staff and property!! Location is primeeeee to walk all around Florence"
United States
Valerie
$184 nightly
The price is $218
Nov 23 - Nov 24
Total with taxes and fees
Il Rivalta - Place of Charme
A rooftop pool with a clear view of historic buildings and mountains in the background.

13. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (155 reviews)
"Great property!"
United States
Jahzier
$172 nightly
The price is $203
Nov 22 - Nov 23
Total with taxes and fees
Teatro Luxury Apartments Firenze - Starhotels Collezione
A bedroom with a bed, bedside tables, a TV, and a wardrobe.

14. Residenza Marchesi Pontenani

Residenza Marchesi Pontenani
Historic Centre of Florence
9.4 out of 10, Exceptional, (32 reviews)
"The host was easy to communicate with, and the location was excellent. The apartment has a fully equipped kitchen, which makes it a great choice for families."
United States
Hyejeong
$82 nightly
The price is $104
Nov 26 - Nov 27
Total with taxes and fees
Residenza Marchesi Pontenani
A balcony with a view of a historic building with a dome and bell tower, surrounded by traditional buildings.

15. Firenze Rentals

Firenze Rentals
Historic Centre of Florence
9.2 out of 10, Wonderful, (476 reviews)
"Stayed at this location for four nights for our first visit to Florence - wonderful location for the tourist attractions, as well food scene. The apartment was spacious, clean and well maintained - with a wonderful air conditioner. Will be staying here again for our next visit."
Canada
Lauren
$181 nightly
The price is $235
Dec 1 - Dec 2
Total with taxes and fees
Firenze Rentals
A dining area with a wooden table set for four, surrounded by chairs. There is a kitchen visible in the background with a 'KITCHEN' sign.

16. Mamo Florence - Ghibellina Apartment

Mamo Florence - Ghibellina Apartment
Historic Centre of Florence
9.0 out of 10, Wonderful, (18 reviews)
"Wonderfully close to Il Duomo and the other sits you will like to visit in Florence."
United States
Charles
$144 nightly
The price is $163
Nov 23 - Nov 24
Total with taxes and fees
Mamo Florence - Ghibellina Apartment
A street with parked scooters and a large wooden door with the number 9.

17. Cozy & Charming Florentine Hideaway

Cozy & Charming Florentine Hideaway
Historic Centre of Florence
9.6 out of 10, Exceptional, (8 reviews)
"Loved our stay. Super spacious and central"
Canada
Sonia
$125 nightly
The price is $143
Nov 12 - Nov 13
Total with taxes and fees
Cozy & Charming Florentine Hideaway
A modern kitchen with a microwave, stove, and a built-in oven. There is a dining area with a round table and yellow chairs.

18. Sapiti Modern by Mmega

Sapiti Modern by Mmega
Historic Centre of Florence
9.4 out of 10, Exceptional, (19 reviews)
"Really convenient location, not crowded at all since it’s not in the center of the city. Everything is close and easy to walk to! The room itself was very clean with two AC units that kept everything a nice temperature. Just be careful going up and down the stairs as they are quite steep and narrow."
Canada
Victoria
$160 nightly
The price is $181
Nov 11 - Nov 12
Total with taxes and fees
Sapiti Modern by Mmega
A hallway leading to a bedroom with a bed, a bedside table, and a nightstand. There is a bathroom with a toilet and a sink. The hallway has a brick wall on one side and a white wall on the other.

19. Casa Dora by Mmega

Casa Dora by Mmega
Historic Centre of Florence
9.2 out of 10, Wonderful, (34 reviews)
"Great location able to walk to many sites in Florence"
Canada
STEPHEN
$211 nightly
The price is $235
Nov 30 - Dec 1
Total with taxes and fees
Casa Dora by Mmega
A bedroom with a bed, a chair, a desk, and a TV.

20. LC41 Suites

LC41 Suites
Oltrarno
9.4 out of 10, Exceptional, (15 reviews)
"Suite was clean and spacious and felt safe in the area. Close to tourist things and great view from room"
Canada
Cari
$101 nightly
The price is $125
Nov 22 - Nov 23
Total with taxes and fees
LC41 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.
View all properties

Learn more about Castellina in Chianti

Medieval stone buildings line the narrow streets where you'll find Tuscany's best wine shops and the fascinating Etruscan tomb museum. Climb the fortress tower for panoramic vineyard views, then join locals at Piazza del Comune for aperitivo hour with regional cheeses.

See all hotels in Castellina in Chianti
A stone building with a clock tower, steps leading up to it, and people walking around.

Top reviews in Castellina in Chianti

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

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti

8/10 Good

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
Reviewed October 14, 2025
Casa Vacanze Squarcialupi

Frequently Asked Questions

What's it like to stay at an apartment in Castellina in Chianti?

You can choose from 16 apartments in Castellina in Chianti for your stay. While in this quaint area, take time to enjoy the countryside or visit the local wineries.

Are you thinking about apartments over traditional hotel rooms?

Often offering more space than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.

What's a favorite apartment I should consider for a stay in Castellina in Chianti?

Here are some of the favorite apartments in the area to choose from: Teatro Luxury Apartments Firenze - Starhotels Collezione: Located in Florence, 21.1 mi/34 km from the heart of Castellina in Chianti. Includes free WiFi and pillowtop beds. A fitness center and onsite laundry facilities are on site. Il Rivalta - Place of Charme: Located 20.7 mi/33.3 km away in Florence. Free WiFi and comfortable bedding are included. A restaurant and valet parking are on site. Firenze Rentals: Located in Florence, 20.7 mi/33.4 km away. Includes free WiFi and pillowtop beds. Access to onsite laundry facilities is available on site. Numa Florence Palazzo San Niccolò: Located 20.3 mi/32.6 km away in Florence. Free WiFi and premium mattresses are included. Onsite laundry facilities and a terrace are on site. Palazzo Branchi: It's located in Florence, 21.4 mi/34.4 km from Castellina in Chianti. Includes free WiFi.

How many apartments can I expect to find in Castellina in Chianti?

Expedia has 16 apartments to book in Castellina in Chianti.

What will the weather be like when I travel to Castellina in Chianti?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Castellina in Chianti. The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.

What should I see and do in Castellina in Chianti?

Castellina in Chianti is known for its wineries and countryside. While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Chianti Sculpture Park. City Hall Castellina In Chianti and Castellina Fortress are other places to visit while you're in town.

What's the best way to get to and around Castellina in Chianti?

Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Florence Airport, Peretola (FLR), which is located 23.2 mi (37.4 km) away from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.

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