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Our top choices for Castellina in Chianti holiday rentals

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (28 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is £154
includes taxes & fees
17 May - 18 May
Riserva di Fizzano Residence

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 £87
includes taxes & fees
25 May - 26 May
Mariani Bed & Breakfast

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 £77
includes taxes & fees
16 May - 17 May
Villa Cristina

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

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 £120
includes taxes & fees
28 May - 29 May
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 £124
includes taxes & fees
21 May - 22 May
Casa Vacanze Squarcialupi

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

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

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 £126
includes taxes & fees
6 Jun - 7 Jun
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

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

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is £4,463
includes taxes & fees
10 May - 11 May
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

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

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (69 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is £52
includes taxes & fees
5 Jun - 6 Jun
Camping Village Il Poggetto.

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (315 reviews)
"Beautiful place for family "
Canada
Ismail
The price is £45
includes taxes & fees
11 May - 12 May
Hu Norcenni Girasole Village

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (85 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is £72
includes taxes & fees
14 May - 15 May
Domus il Palio B&B

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 £105
includes taxes & fees
26 May - 27 May
B&B Il Corso

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (241 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 £98
includes taxes & fees
4 Jun - 5 Jun
La Terrazza Sul Campo Rooming House

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (338 reviews)
"Great stay highly recommend!!"
United States
jon
The price is £68
includes taxes & fees
17 May - 18 May
ApartHotel Anghel

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (69 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is £114
includes taxes & fees
18 May - 19 May
Regis Condo

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 £170
includes taxes & fees
10 May - 11 May
PALAZZO DEL PAPA
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Top Castellina in Chianti Hotel Reviews

Find out more about Castellina in Chianti

Everything you need to know about Castellina in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castellina in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castellina in Chianti holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castellina in Chianti holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castellina in Chianti. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castellina in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castellina in Chianti holiday rentals we have selected for you start as low as £39 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castellina in Chianti rentals

At Expedia, we put the best Castellina in Chianti holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Castellina in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castellina in Chianti holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castellina in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday 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 holiday rental also comes with free parking to give you added peace of mind.

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

With 24 Expedia holiday rentals, you're guaranteed 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 holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.