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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Castellina in Chianti vacation rentals

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1. 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 P5,611
P6,455 total
includes taxes & fees
Aug 5 - Aug 6
Mariani Bed & Breakfast
Terrace/patio

2. 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 P7,974
P9,195 total
includes taxes & fees
Aug 21 - Aug 22
Casa Vacanze Squarcialupi
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

3. 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 P7,459
P8,485 total
includes taxes & fees
Aug 30 - Aug 31
Residenzia del Sogno
Aerial view

4. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is P14,445
P16,030 total
includes taxes & fees
Aug 24 - Aug 25
Riserva di Fizzano Residence
Egyptian cotton sheets, premium bedding, down comforters

5. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (676 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is P5,523
P6,917 total
includes taxes & fees
Aug 9 - Aug 10
Sette Angeli Rooms
View from property

6. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.6 out of 10, Exceptional, (185 reviews)
"Rooms were very clean, and the staff was extremely friendly. The check-in process was very easy and we had a great stay."
United States
Erin
The price is P6,847
P8,373 total
includes taxes & fees
Aug 16 - Aug 17
Dimora Bandinelli Firenze
Room amenity

7. San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (445 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
The price is P13,192
P15,352 total
includes taxes & fees
Sep 3 - Sep 4
San Giuliano Inn - Adults Only
Free daily buffet breakfast

8. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 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 P19,107
P21,298 total
includes taxes & fees
Aug 13 - Aug 14
Terre di Baccio
Exterior

9. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is P20,047
P22,613 total
includes taxes & fees
Aug 9 - Aug 10
Borgo Argenina
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 Paris

Hotel Paris

10/10 Excellent
"We had such an amazing experience at this property. We were visiting for my birthday and the staff made me feel very special by giving us complimentary drinks. We got to stay in the most beautiful hotel room I have ever been in. We felt so blessed and lucky and truly in awe the whole time. The property is minutes away from the Duomo and many other sites. Highly recommend, thank you for the amazing stay!"
Jordyn 2-night trip
Posted 3 hours ago
Hotel Paris

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 30 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 Alta Val d'Elsa River Park. While here, Buondonno Winery and City Hall Castellina In Chianti 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.