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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Top Holiday Rentals in Chianti Region

Lobby lounge
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,575
฿5,033 total
includes taxes & fees
9 Dec - 10 Dec
Villa Cassia di Baccano
Exterior detail
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ฿4,784
฿5,411 total
includes taxes & fees
24 Dec - 25 Dec
Villa il Fedino
Property amenity
Antica Pieve B&B

Townhouse in 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
The price is ฿3,040
฿4,235 total
includes taxes & fees
8 Dec - 9 Dec
Antica Pieve B&B
Aerial view
Relais Villa Olmo

Residence in Impruneta

9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
The price is ฿4,019
฿4,533 total
includes taxes & fees
7 Dec - 8 Dec
Relais Villa Olmo
Front of property
L' Eroico

Townhouse in 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
Apartment, 2 Bedrooms | Premium bedding, down duvets, in-room safe, blackout curtains
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
Terre di Baccio
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Aparthotel in Figline e Incisa Valdarno

9.2 out of 10, Wonderful, (69)
"Very nice place"
United States
Maria
The price is ฿3,342
฿3,732 total
includes taxes & fees
8 Dec - 9 Dec
Relais Villa Belvedere
Terrace/patio
B&B La Fonte del Machiavelli

Townhouse in 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
The price is ฿3,850
฿4,384 total
includes taxes & fees
8 Dec - 9 Dec
B&B La Fonte del Machiavelli
Full-sized fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Residence in Impruneta

3.0 star property
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
Rocca Palazzaccio
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool 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
The price is ฿4,391
฿4,978 total
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno
Outdoor pool, pool loungers
Rocca di Castagnoli

Townhouse in 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
The price is ฿7,599
฿8,656 total
includes taxes & fees
3 Jan - 4 Jan 2026
Rocca di Castagnoli
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

Townhouse in Barberino Tavarnelle

9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Residence in 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
The price is ฿5,235
฿5,759 total
includes taxes & fees
7 Dec - 8 Dec
Relais Villa Belpoggio - Residenza d'Epoca
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
The price is ฿3,993
฿4,616 total
includes taxes & fees
21 Dec - 22 Dec
Casa Vacanze Squarcialupi
Seasonal outdoor pool
Agriturismo La Ferrozzola

Holiday Home in Castellina in Chianti

9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Front of property
Borgo Antico Residence

Apartment in Certaldo Alto

10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is ฿2,818
฿4,140 total
includes taxes & fees
2 Jan - 3 Jan 2026
Borgo Antico Residence
Outdoor pool, pool loungers
I Parigi Corbinelli

Townhouse in Florence

9.4 out of 10, Exceptional, (161)
"I Parigi Corbinelli is a Tuscan treasure - welcoming, clean and luxurious. Grazie mille."
Australia
Tim
The price is ฿2,517
฿3,214 total
includes taxes & fees
15 Dec - 16 Dec
I Parigi Corbinelli
Terrace/patio
Casa Vacanze Le Fornaci

Apartment in 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
The price is ฿4,188
฿4,718 total
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci
Exterior
Sportland

Townhouse in Colle di Val d'Elsa

7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Interior
Residence Il Connubio

Residence in Impruneta

3.0 star property
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
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

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 6 days ago
Hotel Borgo di Cortefreda Relais

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