A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Castellina in Chianti vacation rentals

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 ￥15,312
￥17,586 total
includes taxes & fees
Jul 14 - Jul 15
Mariani Bed & Breakfast
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (34 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ￥41,396
￥45,907 total
includes taxes & fees
Jul 29 - Jul 30
Riserva di Fizzano Residence
Property grounds

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
Exterior

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥40,098
￥50,123 total
includes taxes & fees
Jul 13 - Jul 14
Casa Marisa in Castellina in Chianti
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
The price is ￥15,282
￥24,630 total
includes taxes & fees
Jul 12 - Jul 13
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
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 ￥24,133
￥27,289 total
includes taxes & fees
Jul 16 - Jul 17
Residenzia del Sogno
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 ￥21,792
￥25,085 total
includes taxes & fees
Aug 2 - Aug 3
Casa Vacanze Squarcialupi
Outdoor dining

The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is ￥46,096
￥53,337 total
includes taxes & fees
Aug 2 - Aug 3
The Arch Among the Hills of Castellina
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
Property grounds

Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.8 out of 10, Excellent, (3 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

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (324 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is ￥15,720
￥17,849 total
includes taxes & fees
Jul 14 - Jul 15
Hu Norcenni Girasole Village
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (83 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is ￥8,065
￥9,429 total
includes taxes & fees
Jul 16 - Jul 17
hu Firenze Certosa camping in town
Seasonal outdoor pool

Camping Village Panoramico Fiesole

Camping Village Panoramico Fiesole
3.0 star property
Fiesole
8.4 out of 10, Very Good, (133 reviews)
"Brand new bungalow. Nice campground."
United States
Gustavo
The price is ￥13,729
￥15,845 total
includes taxes & fees
Jul 24 - Jul 25
Camping Village Panoramico Fiesole
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is ￥12,506
￥14,499 total
includes taxes & fees
Jul 15 - Jul 16
Domus il Palio B&B
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (342 reviews)
"Great stay highly recommend!!"
United States
jon
The price is ￥14,035
￥16,182 total
includes taxes & fees
Jul 11 - Jul 12
ApartHotel Anghel
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is ￥18,790
￥21,412 total
includes taxes & fees
Jul 14 - Jul 15
B&B Il Corso
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, (248 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is ￥19,543
￥22,241 total
includes taxes & fees
Jul 12 - Jul 13
La Terrazza Sul Campo Rooming House
Double Room | Minibar, desk, blackout drapes, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (108 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 ￥28,479
￥32,070 total
includes taxes & fees
Jul 11 - Jul 12
PALAZZO DEL PAPA
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (463 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 ￥21,223
￥24,088 total
includes taxes & fees
Jul 13 - Jul 14
Siena Vip
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is ￥47,390
￥53,243 total
includes taxes & fees
Jul 16 - Jul 17
2 Cuori e 1 Yurta Glamping in Toscana
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

Aurum Firenze

Aurum Firenze

10/10 Excellent
"Good service and the room was clean"
Miguel 2-night trip
Posted 3 hours ago
Aurum Firenze

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 Villa with large garden in the Chianti hills and Farmhouse in the heart of the real chiantishire.

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

With 26 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 Castellina Fortress 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.