Castellina in Chianti Vacation Rentals

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Our top choices for Castellina in Chianti vacation rentals

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
4.0 star property
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola

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
Castellina in Chianti
$138 nightly
The price is $143
Jan 13 - Jan 14
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

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
$120 nightly
The price is $134
Jan 18 - Jan 19
Total with taxes and fees
Casa Vacanze Squarcialupi

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
$6,052 nightly
The price is $6,052
Jan 13 - Jan 14
Total with taxes and fees
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (406 reviews)
"Great inn. "
United States
Carol
$92 nightly
The price is $116
Jan 18 - Jan 19
Total with taxes and fees
San Giuliano Inn - Adults Only

Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
9.8 out of 10, Exceptional, (153 reviews)
"Room was large & well appointed. Bathroom was new with update products. Staff was great."
United States
John
Residenza La Musa Amarcord

Sette Angeli Rooms

Sette Angeli Rooms
5.0 star property
Historic Centre of Florence
8.8 out of 10, Excellent, (636 reviews)
"Very convenient. Rooms are small but ok for a couple of nights in Florence. Staff were very helpful. Fantastic location! "
Australia
Suzanne
$63 nightly
The price is $84
Jan 18 - Jan 19
Total with taxes and fees
Sette Angeli Rooms

Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.8 out of 10, Exceptional, (7 reviews)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
$161 nightly
The price is $163
Jan 13 - Jan 14
Total with taxes and fees
Exclusive Stone Tower.

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (423 reviews)
"The staff was great and the location was ideal to explore the Tuscany area"
United States
Juan
$87 nightly
The price is $100
Jan 13 - Jan 14
Total with taxes and fees
Siena Vip

B&B Il Corso

B&B Il Corso
3.0 star property
Siena City Centre
9.8 out of 10, Exceptional, (192 reviews)
"Safe, clean, close to all attractions"
Canada
Carlo
$106 nightly
The price is $122
Feb 10 - Feb 11
Total with taxes and fees
B&B Il Corso

PALAZZO DEL PAPA

PALAZZO DEL PAPA
3.5 star property
Siena City Centre
9.6 out of 10, Exceptional, (97 reviews)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$140 nightly
The price is $159
Jan 30 - Jan 31
Total with taxes and fees
PALAZZO DEL PAPA

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (66 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
Regis Condo

ApartHotel Anghel

ApartHotel Anghel
3.5 star property
Siena
8.4 out of 10, Very Good, (335 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
4.0 star property
Siena City Centre
9.8 out of 10, Exceptional, (63 reviews)
"Excellent host and location!"
United States
Kimberly
$92 nightly
The price is $106
Jan 13 - Jan 14
Total with taxes and fees
B&B Palazzo del Magnifico

Domus il Palio B&B

Domus il Palio B&B
3.0 star property
Ravacciano
9.2 out of 10, Wonderful, (82 reviews)
"Great service Thanks "
Canada
Nelson
$59 nightly
The price is $70
Jan 17 - Jan 18
Total with taxes and fees
Domus il Palio B&B

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
4.0 star property
Siena City Centre
9.6 out of 10, Exceptional, (195 reviews)
"Great location and friendly staff. "
United States
Parissa
$154 nightly
The price is $175
Jan 16 - Jan 17
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
3.5 star property
Siena City Centre
9.8 out of 10, Exceptional, (239 reviews)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Palazzo al Torrione 2

Palazzo al Torrione 2
3.0 star property
San Gimignano City Centre
9.2 out of 10, Wonderful, (107 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
$114 nightly
The price is $131
Jan 19 - Jan 20
Total with taxes and fees
Palazzo al Torrione 2

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (111 reviews)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco

Villa il Fedino

Villa il Fedino
4.0 star property
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97 reviews)
"Great people, great location great service"
Canada
James
$139 nightly
The price is $158
Feb 12 - Feb 13
Total with taxes and fees
Villa il Fedino
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Top Castellina in Chianti Hotel Reviews

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 $58 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?

Farmhouse in the heart of the real chiantishire: This Castellina in Chianti vacation home rental is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Castellina in Chianti include Villa with large garden in the Chianti hills and detached villa with private pool and garden.

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 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.