Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Chianti Region vacation rentals

Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$142 nightly
The price is $157
Jan 8 - Jan 9, 2026
Total with taxes and fees
Villa Cassia di Baccano
Property amenity
Antica Pieve B&B

Antica Pieve B&B

Barberino Tavarnelle
9.4 out of 10, Exceptional, (14)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
$116 nightly
The price is $133
Dec 10 - Dec 11
Total with taxes and fees
Antica Pieve B&B
Terrace/patio
B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
$115 nightly
The price is $132
Dec 16 - Dec 17
Total with taxes and fees
B&B La Fonte del Machiavelli
Exterior detail
Villa il Fedino

Villa il Fedino

San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
$138 nightly
The price is $157
Jan 7 - Jan 8, 2026
Total with taxes and fees
Villa il Fedino
Outdoor pool, sun loungers
I Parigi Corbinelli

I Parigi Corbinelli

Florence
9.4 out of 10, Exceptional, (162)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
$73 nightly
The price is $95
Dec 13 - Dec 14
Total with taxes and fees
I Parigi Corbinelli
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$64 nightly
The price is $73
Dec 16 - Dec 17
Total with taxes and fees
Chianti Village Morrocco
Full-size fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Rocca Palazzaccio

3.0 star property
Impruneta
9.0 out of 10, Wonderful, (14)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
$262 nightly
The price is $292
Dec 20 - Dec 21
Total with taxes and fees
Rocca Palazzaccio
Front of property
L' Eroico

L' Eroico

Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
$95 nightly
The price is $107
Dec 10 - Dec 11
Total with taxes and fees
Relais Villa Belvedere
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
$164 nightly
The price is $180
Dec 10 - Dec 11
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

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
$123 nightly
The price is $137
Jan 7 - Jan 8, 2026
Total with taxes and fees
Casa Vacanze Squarcialupi
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

Pergine Valdarno
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
$131 nightly
The price is $148
Jan 3 - Jan 4, 2026
Total with taxes and fees
Casa Vacanze Le Fornaci
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Residenzia del Sogno

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
$138 nightly
The price is $156
Jan 2 - Jan 3, 2026
Total with taxes and fees
Residenzia del Sogno
Exterior
Sportland

Sportland

Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
Terre di Baccio

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
$253 nightly
The price is $283
Dec 27 - Dec 28
Total with taxes and fees
Terre di Baccio
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Interior
Residence Il Connubio

Residence Il Connubio

3.0 star property
Impruneta
8.8 out of 10, Excellent, (32)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
Residence Il Connubio
Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
$129 nightly
The price is $147
Dec 16 - Dec 17
Total with taxes and fees
Agriturismo La Ferrozzola
Front of property
Borgo Antico Residence

Borgo Antico Residence

Certaldo Alto
10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
$115 nightly
The price is $130
Jan 3 - Jan 4, 2026
Total with taxes and fees
Borgo Antico Residence
Outdoor pool, sun loungers
Rocca di Castagnoli

Rocca di Castagnoli

Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
$238 nightly
The price is $271
Jan 1 - Jan 2, 2026
Total with taxes and fees
Rocca di Castagnoli
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 Chianti Region Hotel Reviews

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 23 hours ago
Castello di Fonterutoli Wine Resort

Find out more about Chianti Region

Everything you need to know about Chianti Region 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 Chianti Region 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 Chianti Region vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chianti Region vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chianti Region. 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 Chianti Region 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 $73 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 Chianti Region rentals

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