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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Castellina in Chianti holiday rentals

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool 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 3.982.516 ₫
4.503.307 ₫ total
includes taxes & fees
20 May - 21 May
Residenzia del Sogno
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is 5.636.718 ₫
6.261.833 ₫ total
includes taxes & fees
20 May - 21 May
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 2.910.300 ₫
3.323.868 ₫ total
includes taxes & fees
17 Jun - 18 Jun
Mariani Bed & Breakfast
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 3.910.218 ₫
4.485.048 ₫ total
includes taxes & fees
21 May - 22 May
Casa Vacanze Squarcialupi
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, (425 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
The price is 6.509.910 ₫
7.529.560 ₫ total
includes taxes & fees
28 May - 29 May
San Giuliano Inn - Adults Only
Deluxe Room, City View | Premium bedding, down duvets, in-room safe, blackout curtains

Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (27 reviews)
"Clean room, amazing staff and service. Would highly recommend to anyone! "
United States
Neil
The price is 7.804.687 ₫
8.953.814 ₫ total
includes taxes & fees
9 Jun - 10 Jun
Maison Ginori Guelfa
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (445 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 3.817.635 ₫
4.322.284 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Siena Vip
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 3.040.393 ₫
3.467.318 ₫ total
includes taxes & fees
4 Jun - 5 Jun
La Terrazza Sul Campo Rooming House
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (88 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is 2.222.411 ₫
2.567.191 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Domus il Palio B&B
Double Room | Minibar, desk, blackout curtains, 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 5.184.412 ₫
5.825.739 ₫ total
includes taxes & fees
25 May - 26 May
PALAZZO DEL PAPA
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 3.133.543 ₫
3.569.783 ₫ total
includes taxes & fees
24 May - 25 May
B&B Il Corso
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

Hotel Albani Firenze

Hotel Albani Firenze

8/10 Good
"Breakfast was excellent.Air quality was good."
Kimberley 2-night trip
Posted 1 hour ago
Hotel Albani Firenze

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.

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

With 23 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 Chianti Sculpture Park. 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.