Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Castellina in Chianti vacation rentals

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ￥20,688
￥23,493 total
includes taxes & fees
Mar 27 - Mar 28
Residenzia del Sogno
Front of property

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 ￥20,243
￥23,005 total
includes taxes & fees
Apr 15 - Apr 16
Agriturismo La Ferrozzola
Panoramic Apartment (2) | Terrace/patio

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 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 ￥20,181
￥23,305 total
includes taxes & fees
Mar 29 - Mar 30
Casa Vacanze Squarcialupi
Dining

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥858,863
￥950,996 total
includes taxes & fees
Mar 27 - Mar 28
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ￥16,709
￥19,117 total
includes taxes & fees
Apr 17 - Apr 18
Mariani Bed & Breakfast
Property grounds

OLIVE TREES HOUSE WITH POOL

OLIVE TREES HOUSE WITH POOL
Castellina in Chianti
OLIVE TREES HOUSE WITH POOL
Outdoor dining

Casa La Misura, garden and pool in the heart of Chianti

Casa La Misura, garden and pool in the heart of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
Casa La Misura, garden and pool in the heart of Chianti
Property grounds

Rondine cosy apartment garden pool tennis wifi

Rondine cosy apartment garden pool tennis wifi
Toscana
Rondine cosy apartment garden pool tennis wifi
Property grounds

House Il Cipresso in the heart of Chianti with swimming pool

House Il Cipresso in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
House Il Cipresso in the heart of Chianti with swimming pool
Terrace/patio

Viniard Villa - Residence Le Rose in Chianti

Viniard Villa - Residence Le Rose in Chianti
Castellina in Chianti
The price is ￥73,706
￥137,093 total
includes taxes & fees
Mar 31 - Apr 1
Viniard Villa - Residence Le Rose in Chianti
Interior

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
The price is ￥16,634
￥25,464 total
includes taxes & fees
Mar 27 - Mar 28
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Property grounds

Casa Antico Roseto with swimming pool in the heart of Chianti

Casa Antico Roseto with swimming pool in the heart of Chianti
Castellina in Chianti
8.0 out of 10, Very Good, (2 reviews)
"The house was very charming 16th century stay. The gated patio off the bedroom was very convenient for morning coffee and evening wine. Such a beautiful countryside. The house is filled with antiques and furnishings, however, it’s time to update the mattresses. Taking the trash 6 minutes away to the indicated bins was a bit of an inconvenience as well. Very centrally located to Olive Oil and Chianti vineyards, a few towns from Panzano and Greece, gorgeous views and sunsets. "
United States
Brenna H.
Casa Antico Roseto with swimming pool in the heart of Chianti
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
10.0 out of 10, Exceptional, (2 reviews)
"The room was perfect, the location is near to all main attractions of the city and is 15 minutes away from the train station."
United States
Rustinko
The price is ￥20,159
￥24,386 total
includes taxes & fees
Mar 31 - Apr 1
Boboli Living
Deluxe Double Room, City View | Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (411 reviews)
"Well located, lovely kind staff beautifully appointed. "
Canada
Nancy
The price is ￥19,193
￥23,324 total
includes taxes & fees
Mar 29 - Mar 30
San Giuliano Inn - Adults Only
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ￥28,745
￥32,357 total
includes taxes & fees
Mar 29 - Mar 30
Villa il Fedino
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (196 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is ￥17,560
￥20,053 total
includes taxes & fees
Mar 29 - Mar 30
B&B Il Corso
Suite | Living room | Flat-screen TV

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239 reviews)
"Huge room! Great location "
Canada
karen
The price is ￥19,894
￥22,620 total
includes taxes & fees
Apr 12 - Apr 13
La Terrazza Sul Campo Rooming House
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (430 reviews)
"Nice place!"
United States
Pavel
The price is ￥17,407
￥19,884 total
includes taxes & fees
Apr 1 - Apr 2
Siena Vip
Double Room | Minibar, desk, blackout drapes, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (97 reviews)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ￥25,350
￥28,622 total
includes taxes & fees
Mar 29 - Mar 30
PALAZZO DEL PAPA
City view

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (68 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is ￥16,082
￥18,427 total
includes taxes & fees
Mar 27 - Mar 28
Regis Condo
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

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"The location of the hotel is great. 5minutes walk to train station walking distance to all places of interest. The staff are very friendly and room is clean. "
Jing 2-night trip
Posted 20 hours ago
Grand Hotel Baglioni

Find out more about Castellina in Chianti

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

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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 vacation rentals in Castellina in Chianti?

Yes, you can find vacation rentals near the most popular attractions in Castellina in Chianti, or you can go with a more remote option if you're looking for relaxation. 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 vacation home rentals in Castellina in Chianti?

Borgo Argiano: This vacation home rental outside Castellina in Chianti is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a coffee maker. You can relax into your vacation with a garden and a library. Some other top choices in Castellina in Chianti are Farmhouse in the heart of the real chiantishire and Villa with large garden in the Chianti hills.

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

With 31 Expedia vacation rentals, you're sure 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 Buondonno Winery are other places worth a visit.

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

A vacation rental is a private property you can stay in for several days or longer in Castellina in Chianti. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family gatherings.