Castellina in Chianti Vacation Rentals

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Vacation Rentals in Castellina in Chianti

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Townhouse in Castellina in Chianti

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
$136 nightly
The price is $155
Jan 2 - Jan 3, 2026
Total with taxes and fees
Residenzia del Sogno
Seasonal outdoor pool
Agriturismo La Ferrozzola

Vacation Home in Castellina in Chianti

9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Apartment in Castellina in Chianti

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
$122 nightly
The price is $136
Dec 5 - Dec 6
Total with taxes and fees
Casa Vacanze Squarcialupi
9 bedrooms, free WiFi
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

Villa in Castellina in Chianti

$6,047 nightly
The price is $6,047
Jan 1 - Jan 2, 2026
Total with taxes and fees
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Outdoor dining
La Misura, cottage with garden and swimming pool on the hills of Chianti

Cottage in Castellina in 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
Pool
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

Cottage in Castellina in Chianti

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Fridge, oven, stovetop, coffee/tea maker
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Apartment in Castellina in Chianti

$128 nightly
The price is $132
Dec 4 - Dec 5
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Birthday party area
Siena Vip

Townhouse in Siena City Centre

9.2 out of 10, Wonderful, (419)
"A great location!"
Canada
Cheryl
$92 nightly
The price is $106
Dec 4 - Dec 5
Total with taxes and fees
Siena Vip
Exterior detail
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

9.6 out of 10, Exceptional, (97)
"We had a wonderfull welcome, very professional ,friendly and helpful in every aspect. Great villa with Tuscany vibe and breathtaking views.Close enough to Florence.You can't ask for better. We will return again."
Canada
Mario
$149 nightly
The price is $169
Dec 18 - Dec 19
Total with taxes and fees
Villa il Fedino
City view from property
Soggiorno Battistero

Townhouse in Historic Centre of Florence

8.8 out of 10, Excellent, (380)
"We were worried about the noise of the busy tourist spot, but the windows were fantastic and was able to sleep soundly. Great location, highly recommend."
Canada
Jason
$76 nightly
The price is $100
Dec 9 - Dec 10
Total with taxes and fees
Soggiorno Battistero
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

Townhouse in Siena City Centre

9.8 out of 10, Exceptional, (190)
"Safe, clean, close to all attractions"
Canada
Carlo
$95 nightly
The price is $109
Dec 8 - Dec 9
Total with taxes and fees
B&B Il Corso
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

9.6 out of 10, Exceptional, (190)
"Great location and friendly staff. "
United States
Parissa
$149 nightly
The price is $169
Dec 13 - Dec 14
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
Exterior
PALAZZO DEL PAPA

Townhouse in Siena City Centre

9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$123 nightly
The price is $140
Dec 8 - Dec 9
Total with taxes and fees
PALAZZO DEL PAPA
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Apartment in Siena City Centre

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
$84 nightly
The price is $97
Dec 18 - Dec 19
Total with taxes and fees
Regis Condo
Lobby lounge
ApartHotel Anghel

Apartment in Siena

8.4 out of 10, Very Good, (333)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
$104 nightly
The price is $119
Jan 3 - Jan 4, 2026
Total with taxes and fees
ApartHotel Anghel
Balcony
Palazzo al Torrione 2

Townhouse in San Gimignano City Centre

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
Dec 15 - Dec 16
Total with taxes and fees
Palazzo al Torrione 2
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers
Tenuta Sant'Ilario

Townhouse in Gambassi Terme

9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
$96 nightly
The price is $110
Dec 4 - Dec 5
Total with taxes and fees
Tenuta Sant'Ilario
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
Terre di Baccio

Townhouse in Greve in Chianti

9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
$245 nightly
The price is $275
Dec 4 - Dec 5
Total with taxes and fees
Terre di Baccio
Terrace/patio
Palazzo Alfieri Residenza d’epoca

Residence in Historic Centre of Florence

9.2 out of 10, Wonderful, (721)
"Very nice hotel with great staff"
United States
Judy
$121 nightly
The price is $150
Dec 9 - Dec 10
Total with taxes and fees
Palazzo Alfieri Residenza d’epoca
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

The Market Urban Hotel

The Market Urban Hotel

10/10 Excellent
"Room was clean. Bathroom was quite small and tight."
Payal 3-night trip
Posted 3 days ago
The Market Urban 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 $63 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 Farmhouse in the heart of the real chiantishire and Villa with large garden in the Chianti hills.

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 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.