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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 1524 Vacation Homes in Castellina in Chianti with updated reviews, rates, and availability.

QK Costa58 Home Tower
Living room

QK Costa58 Home Tower

9.6 out of 10, Exceptional, (125)
"Beautiful property, very spacious with a little kitchen. Grocery store is walking distance. Staff is very friendly.stayed almost 2 weeks. Loved it! Will be back💗"
The price is AED 494
AED 589 total
includes taxes & fees
25 Mar - 26 Mar
QK Costa58 Home Tower
Apartment PonteVecchio Signoria
Interior

Apartment PonteVecchio Signoria

10.0 out of 10, Exceptional, (16)
"Lorenzo was a wonderful host. He took care of everything! He helped with luggage, and was so very kind. It was a pleasure to meet Lorenzo and stay in his beautiful apartment. It was the perfect location too, near the Ponte Vecchio and close to everything! Thank you, Lorenzo!"
Apartment PonteVecchio Signoria
B&B Liveinflorence Centro Storico
Room

B&B Liveinflorence Centro Storico

10.0 out of 10, Exceptional, (1)
"Pulitissimo e centralissino"
The price is AED 768
AED 1,006 total
includes taxes & fees
23 Feb - 24 Feb
B&B Liveinflorence Centro Storico
Beautiful stone house with garden and private pool.
Property grounds

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.
Farmhouse in the heart of the real chiantishire
Entrance

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (131)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
Panoramic villa w/ private infinity pool & garden
Outdoor dining

Panoramic villa w/ private infinity pool & garden

9.2 out of 10, Wonderful, (30)
"We loved our stay in the villa. The location felt rural enough but was also only a 10 minute walk into town (it’s a bit steep though) where there were some great bars, restaurants and a little shop. The pool has a great view and there is plenty of land (including an onsite vineyard). We had some challenges finding the villa by car due to some roadworks and the person who met us did not speak any English (we don’t speak any Italian), however a call to the property managing agent sorted this out....
Panoramic villa w/ private infinity pool & garden
Tuscan house in an ancient village near San Gimignano - Il Fienile
Natural bio pool with a spectacular view

Tuscan house in an ancient village near San Gimignano - Il Fienile

9.8 out of 10, Exceptional, (51)
"Excellent and quick contact with property owner. She was very responsive when I had to make very rapid arrangements (less than 72 hours) after a different VRBO didn't work out. Upon our arrival, Roberto (the property manager - lovely gentleman - very prompt and responsive), helped us to understand the property and it's layout. We felt well-prepared and faced no difficulties during our stay. Roberto speaks Italian and English and we speak mostly English with just enough Italian to be...
Tuscan house in an ancient village near San Gimignano - Il Fienile
The One and Only: NEW ROYAL SUITE with PRIVATE TERRACE OVERLOOKING FLORENCE
Outdoor spa tub

The One and Only: NEW ROYAL SUITE with PRIVATE TERRACE OVERLOOKING FLORENCE

9.6 out of 10, Exceptional, (35)
"Spent a few days exploring central Florence by foot and the view and location of the apartment can’t be beat. "
The price is AED 653
AED 1,222 total
includes taxes & fees
23 Feb - 24 Feb
The One and Only: NEW ROYAL SUITE with PRIVATE TERRACE OVERLOOKING FLORENCE
SUITE with a secret historical crypt in Florence Ponte Vecchio
Living area

SUITE with a secret historical crypt in Florence Ponte Vecchio

9.0 out of 10, Wonderful, (14)
"Wonderful location! Wonderful apartment. Great food and sites to see . Might recommend updating your listing to include that there are local city taxes and that you only accept PayPal for the city tax payment . "
The price is AED 607
AED 1,072 total
includes taxes & fees
23 Feb - 24 Feb
SUITE with a secret historical crypt in Florence Ponte Vecchio
Chianti Craft House Badia a Passignano
Point of interest

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"The apartment is at the heart of the small village, central to several great restaurants and practically across the street from the incredible 11th century abbey. The place was very clean and has been recently renovated, but still had a very historic feel to it. Emanuel, our host, was very friendly and gracious. He offered several personal recommendations to restaurants and a wine tasting at a nearby castle, all of which were great! Would definitely stay here again!"
The price is AED 634
AED 880 total
includes taxes & fees
23 Mar - 24 Mar
Chianti Craft House Badia a Passignano
Charming apartment in the Historic Center of Siena
Total view

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"This is a wonderful place. It was clean and spacious. It was well stocked. It even had bread and jam for us. It had a kitchen well-stocked with pots, pans, silverware and plates. The owner, Daniella, runs the clothing store in the same building and was very accessible and helpful. It is close by restaurants and shops and was even a nice sized Pam Local supermarket just a few doors away."
The price is AED 461
AED 791 total
includes taxes & fees
23 Feb - 24 Feb
Charming apartment in the Historic Center of Siena
The Photographer's House
Living area

The Photographer's House

9.8 out of 10, Exceptional, (9)
"The house is spacious, interesting and has everything needed for a holiday. The garden is a huge bonus - room to relax with a view (and grapes on the vine!). It was a joy to stay in an historic house in such an interesting town, with shops and restaurants within easy walking distance. We had a delicious meal at the owner’s restaurant too."
The Photographer's House
Volterra Countryside House
Living area

Volterra Countryside House

9.6 out of 10, Exceptional, (14)
"Lots of room on 3 floors very close to all the sites"
Volterra Countryside House
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Interior

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Holiday home in the Florentine Chianti half an hour from Florence
Property grounds

Holiday home in the Florentine Chianti half an hour from Florence

9.8 out of 10, Exceptional, (52)
"My wife and I spent nine nights is this spacious and well-equipped home in the quiet village of Montespertoli in the Chianti region of Tuscany. Bruno was a wonderful host, always quick to respond to our questions. He left the home equipped well for our first night or two and directed us to the Co-Op grocery store only a 3-4 minute walk from the front door. Our rental car was securely parked in his garage every night, so no need to park on the street or worry about not finding a place close to...
Holiday home in the Florentine Chianti half an hour from Florence
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Pool

Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.

9.8 out of 10, Exceptional, (59)
"My wife and I had a wonderful time. Our host Marilia is lovely and gave very helpful recommendations for vineyards, restaurants and cooking classes in the area. The view and surrounding area is breathtaking!"
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Wonderful Tuscan farmhouse with large spaces and panoramic views
Room

Wonderful Tuscan farmhouse with large spaces and panoramic views

10.0 out of 10, Exceptional, (11)
"We had a great time. The vila was everything we expected and our host was very accessible. I would highly recommend."
Wonderful Tuscan farmhouse with large spaces and panoramic views
Typical Tuscan Country House
Facade

Typical Tuscan Country House

10.0 out of 10, Exceptional, (114)
"Nice tidy property with everything we needed for a great stay, great location and lovely and helpful host."
Typical Tuscan Country House
House with swimming pool. Medieval village in the heart of Chianti Classico
Pool

House with swimming pool. Medieval village in the heart of Chianti Classico

10.0 out of 10, Exceptional, (106)
"Nice townhouse in a wonderfully centralized area. We wanted to explore the Chianti region from a 'home-base' and the Castellina in Chianti area was ideal for us."
House with swimming pool. Medieval village in the heart of Chianti Classico
Holiday house with private pool and fenced garden
Terrace/patio

Holiday house with private pool and fenced garden

10.0 out of 10, Exceptional, (49)
"We really enjoyed our 10 day stay, beds were comfortable and everything was clean, the pool was fantastic with an amazing view. Lots of space for two couples to relax and unwind yet within an hour of all the major towns and attractions. Jurgen was responsive to our needs and even helped us with the pizza oven. We will definitely consider staying here again."
Holiday house with private pool and fenced garden
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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Other property types in Castellina in Chianti

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
View from the dining room table

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Farmhouse in the heart of the real chiantishire
Entrance

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (131)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
House in a typical village in the heart of Chianti
Exterior

House in a typical village in the heart of Chianti

9.4 out of 10, Exceptional, (34)
"It's a great home base to start exploring the region. Two wineries are very close by, and Florence is an easy drive away. The traditional way the house is built keeps it nice and cold during the day. We loved it!"
House in a typical village in the heart of Chianti
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.