Castellina in Chianti Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Vacation Rentals in Castellina in Chianti

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno
Residenzia del Sogno
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$127 nightly
The price is $145
Oct 27 - Oct 28
Total with taxes and fees
Residenzia del Sogno
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi
Casa Vacanze Squarcialupi
8.0 out of 10, Very Good, (2)
"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
$118 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
Casa Vacanze Squarcialupi
Seasonal outdoor pool
Agriturismo La Ferrozzola
Agriturismo La Ferrozzola
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
$133 nightly
The price is $151
Nov 2 - Nov 3
Total with taxes and fees
Agriturismo La Ferrozzola
Outdoor dining
La Misura, cottage with garden and swimming pool on the hills of Chianti
La Misura, cottage with garden and swimming pool on the hills of Chianti
10.0 out of 10, Exceptional, (2)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti
Fridge, oven, stovetop, coffee/tea maker
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
$133 nightly
The price is $137
Nov 3 - Nov 4
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Pool
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Chalet | 1 bedroom, in-room safe, cribs/infant beds, bed sheets
Hu Firenze Camping In Town
Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1576)
"It was a grt place to stay"
United States
Sunitha
$48 nightly
The price is $61
Nov 23 - Nov 24
Total with taxes and fees
Hu Firenze Camping In Town
Food and drink
San Giuliano Inn - Adults Only
San Giuliano Inn - Adults Only
10.0 out of 10, Exceptional, (393)
"Great location - we loved it!"
United States
Julian
$144 nightly
The price is $173
Nov 8 - Nov 9
Total with taxes and fees
San Giuliano Inn - Adults Only
Quadruple Room, City View | 1 bedroom, desk, iron/ironing board, free WiFi
Al Mercato B&B
Al Mercato B&B
9.0 out of 10, Wonderful, (91)
"Nice area and clean property "
United States
heeman
$74 nightly
The price is $86
Nov 17 - Nov 18
Total with taxes and fees
Al Mercato B&B
Bar (on property)
Il Battistero Siena - Residenza d'Epoca
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (186)
"Great location and friendly staff. "
United States
Parissa
$144 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
Lobby lounge
ApartHotel Anghel
ApartHotel Anghel
8.4 out of 10, Very Good, (329)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
$74 nightly
The price is $86
Nov 2 - Nov 3
Total with taxes and fees
ApartHotel Anghel
Birthday party area
Siena Vip
Siena Vip
9.2 out of 10, Wonderful, (410)
"Super clean super close to everything."
United States
Ramon
$106 nightly
The price is $122
Nov 2 - Nov 3
Total with taxes and fees
Siena Vip
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House
La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Gazebo
Domus il Palio B&B
Domus il Palio B&B
9.2 out of 10, Wonderful, (79)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B
Exterior
Podere La Chiusella
Podere La Chiusella
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo
Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
2 bars/lounges
Camping Boschetto Di Piemma
Camping Boschetto Di Piemma
3.0 star property
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
Balcony
Palazzo al Torrione 2
Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
$120 nightly
The price is $138
Nov 20 - Nov 21
Total with taxes and fees
Palazzo al Torrione 2
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso
B&B Il Corso
9.8 out of 10, Exceptional, (186)
"Everything we like overall. Wish we stayed there more. "
United States
Mira
$95 nightly
The price is $109
Nov 10 - Nov 11
Total with taxes and fees
B&B Il Corso
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (107)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$70 nightly
The price is $80
Oct 30 - Oct 31
Total with taxes and fees
Chianti Village Morrocco
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Solo Experience Hotel

Solo Experience Hotel

10/10 Excellent
"This hotel is in a great location, very walkable to all the sites and restaurants. We didn't hear any noise from the market nearby or other hotel guests. Rachel the attendant at breakfast is AMAZING and made our stay even better. I would highly recommend this hotel and would stay again if I'm in Florence."
Keri 3-night trip
Posted 22 hours ago
Solo Experience Hotel

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 $61 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.

Explore a world of travel with Expedia

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?

QK Costa58 Home Tower: This vacation home rental outside Castellina in Chianti is located in the historical district and offers a terrace, air-conditioning, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. 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 82 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 Borgo di Vescine - Tenute di Castelvecchi, 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 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.