Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Castellina in Chianti vacation rentals

Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (28 reviews)
"We loved it!"
United States
Juliette
The price is ￥31,071
￥34,549 total
includes taxes & fees
May 17 - May 18
Riserva di Fizzano Residence
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 ￥16,192
￥18,552 total
includes taxes & fees
Jun 4 - Jun 5
Mariani Bed & Breakfast
Outdoor dining

Casa il Cipresso, in the heart of Chianti with swimming pool

Casa 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.
Casa il Cipresso, in the heart of Chianti with swimming pool
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 ￥24,008
￥27,148 total
includes taxes & fees
May 25 - May 26
Residenzia del Sogno
Garden

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
The price is ￥14,398
￥16,578 total
includes taxes & fees
May 16 - May 17
Villa Cristina
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 ￥23,753
￥27,236 total
includes taxes & fees
May 21 - May 22
Casa Vacanze Squarcialupi
Outdoor dining

La Misura, cottage with garden and swimming pool on the hills of Chianti

La Misura, cottage with garden and swimming pool on the hills 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.
La Misura, cottage with garden and swimming pool on the hills of Chianti
Property grounds

Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi

Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
Toscana
Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
Dining

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥860,780
￥953,119 total
includes taxes & fees
May 17 - May 18
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Exterior

Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
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 - cottage with swimming pool
Exterior

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

Rondine cosy apartment in the Chianti garden pool tennis wifi

Rondine cosy apartment in the Chianti garden pool tennis wifi
Toscana
Rondine cosy apartment in the Chianti garden pool tennis wifi
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
8.6 out of 10, Excellent, (8 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 ￥25,517
￥30,284 total
includes taxes & fees
May 20 - May 21
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, (420 reviews)
"Wonderful place and staff"
United Kingdom
Simone
The price is ￥39,256
￥45,405 total
includes taxes & fees
May 26 - May 27
San Giuliano Inn - Adults Only
Business Room, 1 Bedroom | Down comforters, desk, cribs/infant beds, rollaway beds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (87 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is ￥13,171
￥15,229 total
includes taxes & fees
May 27 - May 28
Domus il Palio B&B
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (242 reviews)
"My first time in Siena and this Rooming House turned out to be a great choice. The view onto the piazza is a real bonus, as is the great location in the heart of the city. The host was lovely and a great communicator. The room itself was fantastic and spacious. I would recommend it and will book again. "
United Kingdom
Jeffrey William
The price is ￥18,334
￥20,909 total
includes taxes & fees
Jun 4 - Jun 5
La Terrazza Sul Campo Rooming House
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (201 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is ￥18,896
￥21,526 total
includes taxes & fees
May 26 - May 27
B&B Il Corso
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (437 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is ￥22,949
￥25,983 total
includes taxes & fees
May 24 - May 25
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, (100 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is ￥30,599
￥34,400 total
includes taxes & fees
May 14 - May 15
PALAZZO DEL PAPA
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

Plus Florence - Hostel

Plus Florence - Hostel

8/10 Good
"Private room was more than adequate for our needs. Terrace view was nice and location was good to walk to attractions. Some guests were a little noisy at night. We’re talking 1am, well after the quiet time suggested at 11pm. "
Margaret 2-night trip
Posted 3 hours ago
Plus Florence - Hostel

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?

Villa La Stella - Casa per Ferie: This vacation 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 vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Castellina in Chianti are Farmhouse in the heart of the real chiantishire and House in a typical village in the heart of Chianti.

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

With 24 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 Sentierelsa Trail. 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.