A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Castellina in Chianti vacation rentals

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

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
$80 nightly
The price is $93
Sep 10 - Sep 11
Total with taxes and fees
Mariani Bed & Breakfast
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

2. 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
$216 nightly
The price is $240
Sep 8 - Sep 9
Total with taxes and fees
Riserva di Fizzano Residence
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

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
$143 nightly
The price is $160
Sep 13 - Sep 14
Total with taxes and fees
Casa Vacanze Squarcialupi
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. 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
$118 nightly
The price is $135
Sep 27 - Sep 28
Total with taxes and fees
Residenzia del Sogno
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. 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
$356 nightly
The price is $397
Sep 25 - Sep 26
Total with taxes and fees
Terre di Baccio
A table with breakfast items and a view of rolling hills.

6. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$81 nightly
The price is $91
Sep 7 - Sep 8
Total with taxes and fees
Chianti Village Morrocco
A table with two wine glasses, a bottle, and a book.

7. 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
$63 nightly
The price is $74
Sep 24 - Sep 25
Total with taxes and fees
Domus il Palio B&B
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

8. 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
$238 nightly
The price is $266
Oct 4 - Oct 5
Total with taxes and fees
PALAZZO DEL PAPA
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

9. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
$160 nightly
The price is $176
Sep 21 - Sep 22
Total with taxes and fees
Villa di Sotto
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

10. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
$144 nightly
The price is $163
Oct 5 - Oct 6
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (476 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
$115 nightly
The price is $131
Sep 7 - Sep 8
Total with taxes and fees
Siena Vip
A bakery display with pastries and a coffee station.

12. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (206 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
$146 nightly
The price is $165
Sep 23 - Sep 24
Total with taxes and fees
B&B Il Corso
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

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
$207 nightly
The price is $232
Sep 14 - Sep 15
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

14. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (345 reviews)
"Great stay highly recommend!!"
United States
jon
$82 nightly
The price is $96
Sep 9 - Sep 10
Total with taxes and fees
ApartHotel Anghel
A villa with a swimming pool, outdoor seating, and a tennis court.

15. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (76 reviews)
"Beautiful property"
Canada
Mary
$149 nightly
The price is $169
Oct 4 - Oct 5
Total with taxes and fees
Villa Curina Resort
A courtyard with a stone statue, a round table, and chairs.

16. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (79 reviews)
"Great location!!! Clean and well equipped. Easy online check process. Comfortable beds and linens. Would highly recommend this property."
United States
kay
$142 nightly
The price is $160
Sep 7 - Sep 8
Total with taxes and fees
Regis Condo
An arched entrance with a lantern above, flanked by two potted plants.

17. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (103 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
$222 nightly
The price is $249
Oct 5 - Oct 6
Total with taxes and fees
Villa il Fedino
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

18. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$46 nightly
The price is $55
Sep 6 - Sep 7
Total with taxes and fees
Camping Boschetto Di Piemma
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

19. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (264 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
$215 nightly
The price is $240
Oct 5 - Oct 6
Total with taxes and fees
Relais Villa Olmo
A pool area with a water slide and a stage for performances.

20. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (331 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
$56 nightly
The price is $64
Sep 10 - Sep 11
Total with taxes and fees
Hu Norcenni Girasole Village
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 Delle Nazioni

Hotel Delle Nazioni

8/10 Good
"1 night stay with my family and it was great."
Jennifer 1-night trip
Posted 1 hour ago
Hotel Delle Nazioni

Find out more about Castellina in Chianti

Everything you need to know about Castellina in Chianti vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castellina in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castellina in Chianti vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castellina in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $60 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 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 Villa with large garden in the Chianti hills and Farmhouse in the heart of the real chiantishire.

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