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Castellina in Chianti Vacation Rentals

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Our top choices for Castellina in Chianti vacation rentals

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 CA $132
CA $151 total
includes taxes & fees
Jul 15 - Jul 16
Mariani Bed & Breakfast

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (33 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is CA $324
CA $359 total
includes taxes & fees
Jul 2 - Jul 3
Riserva di Fizzano Residence

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 CA $207
CA $234 total
includes taxes & fees
Jul 8 - Jul 9
Residenzia del Sogno

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 CA $205
CA $235 total
includes taxes & fees
Jul 4 - Jul 5
Casa Vacanze Squarcialupi

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is CA $249
CA $286 total
includes taxes & fees
Jul 2 - Jul 3
Villa Curina Resort

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (93 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 CA $101
CA $117 total
includes taxes & fees
Jul 7 - Jul 8
Domus il Palio B&B

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 CA $74
CA $86 total
includes taxes & fees
Jul 7 - Jul 8
hu Firenze Certosa camping in town

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (107 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 CA $246
CA $277 total
includes taxes & fees
Jul 8 - Jul 9
PALAZZO DEL PAPA

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 CA $164
CA $187 total
includes taxes & fees
Jul 5 - Jul 6
B&B Il Corso

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (461 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 CA $185
CA $210 total
includes taxes & fees
Jul 13 - Jul 14
Siena Vip

Regis Condo

Regis Condo
Siena City Centre
9.2 out of 10, Wonderful, (74 reviews)
"I loved the location. My only problem was having to wake-up by a jackhammer in the morning as the hotel was remodeling the apartment next door."
United States
Dror
The price is CA $184
CA $209 total
includes taxes & fees
Jul 13 - Jul 14
Regis Condo

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 CA $171
CA $194 total
includes taxes & fees
Jul 15 - Jul 16
La Terrazza Sul Campo Rooming House

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (340 reviews)
"Great stay highly recommend!!"
United States
jon
The price is CA $117
CA $135 total
includes taxes & fees
Jul 21 - Jul 22
ApartHotel Anghel

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $150
CA $214 total
includes taxes & fees
Jul 5 - Jul 6
Palazzo al Torrione 2

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is CA $414
CA $465 total
includes taxes & fees
Jul 6 - Jul 7
2 Cuori e 1 Yurta Glamping in Toscana

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is CA $543
CA $611 total
includes taxes & fees
Jul 3 - Jul 4
Borgo Argenina

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (76 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is CA $402
CA $449 total
includes taxes & fees
Jul 9 - Jul 10
Terre di Baccio

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is CA $100
CA $113 total
includes taxes & fees
Jul 2 - Jul 3
Chianti Village Morrocco

Guild Siena Senior Resort & Residence

Guild Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (48 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
The price is CA $201
CA $228 total
includes taxes & fees
Jul 13 - Jul 14
Guild Siena Senior Resort & Residence

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very good, (252 reviews)
"Nice inn on a working farm located deep in the hills of suburban Florence."
United States
Allan
The price is CA $105
CA $138 total
includes taxes & fees
Jul 5 - Jul 6
Fattoria il Milione Agriturismo
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

Find out more about Castellina in Chianti

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Castellina in Chianti. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Villa with large garden in the Chianti hills.

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

With 25 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.