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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Castellina in Chianti vacation rentals

Lounge

1. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is P5,598
P6,445 total
includes taxes & fees
Oct 7 - Oct 8
Mariani Bed & Breakfast
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

2. 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 P8,085
P9,182 total
includes taxes & fees
Oct 6 - Oct 7
Residenzia del Sogno
Terrace/patio

3. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 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 P8,665
P9,964 total
includes taxes & fees
Oct 18 - Oct 19
Casa Vacanze Squarcialupi
Aerial view

4. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is P12,374
P13,755 total
includes taxes & fees
Oct 8 - Oct 9
Riserva di Fizzano Residence
View from room

5. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (119 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is P4,623
P5,229 total
includes taxes & fees
Oct 15 - Oct 16
Chianti Village Morrocco
Exterior

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is P12,128
P13,917 total
includes taxes & fees
Sep 22 - Sep 23
Borgo Argenina
Free daily buffet breakfast

7. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is P25,042
P27,834 total
includes taxes & fees
Sep 21 - Sep 22
Terre di Baccio
Property grounds

8. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 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 P4,478
P5,214 total
includes taxes & fees
Oct 12 - Oct 13
Domus il Palio B&B
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

9. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is P9,969
P10,966 total
includes taxes & fees
Sep 21 - Sep 22
Villa di Sotto
Room amenity

10. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (478 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is P7,159
P8,163 total
includes taxes & fees
Sep 21 - Sep 22
Siena Vip
Breakfast meal

11. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (208 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is P7,290
P8,307 total
includes taxes & fees
Sep 27 - Sep 28
B&B Il Corso
Lobby lounge

12. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (347 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is P5,771
P6,636 total
includes taxes & fees
Sep 25 - Sep 26
ApartHotel Anghel
Premium bedding, Select Comfort beds, minibar, in-room safe

13. 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 P12,011
P13,500 total
includes taxes & fees
Oct 5 - Oct 6
La Terrazza Sul Campo Rooming House
Aerial view

14. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (79 reviews)
"Unique property good value staff was great. Nice location to other areas"
United States
Joe
The price is P10,827
P12,198 total
includes taxes & fees
Sep 20 - Sep 21
Villa Curina Resort
Minibar, desk, blackout drapes, WiFi (free)

15. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 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 P14,862
P16,636 total
includes taxes & fees
Sep 23 - Sep 24
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

Hotel Santa Maria Novella

Hotel Santa Maria Novella

10/10 Excellent
"Amazing and historical place to stay! Loved everything about it, including the amazing location, helpful stuff, and the historical building."
Shakil 4-night trip
Posted 10 hours ago
Hotel Santa Maria Novella

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.

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

With 28 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.