Chianti Region Vacation Rentals

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Our top choices for Chianti Region vacation rentals

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
$89 nightly
The price is $101
Nov 29 - Nov 30
Total with taxes and fees
Relais Villa Olmo - Place of Charme

2. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
$58 nightly
The price is $66
Dec 15 - Dec 16
Total with taxes and fees
Chianti Village Morrocco

3. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$114 nightly
The price is $127
Dec 4 - Dec 5
Total with taxes and fees
Palazzo Pacini

4. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
$105 nightly
The price is $120
Dec 9 - Dec 10
Total with taxes and fees
Antica Pieve B&B

5. LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
$167 nightly
The price is $167
Nov 16 - Nov 17
Total with taxes and fees
LARGE, OPEN-AIR TERRACE WITH VIEWS OF THE CHAINTI VALLEY AND DRINKS

6. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
$235 nightly
The price is $263
Nov 15 - Nov 16
Total with taxes and fees
Terre di Baccio

7. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (176 reviews)
"Fabulous breakfast, wonderful views from breakfast room and garden. Very helpful staff, suggesting local restaurants and things to do."
United Kingdom
Susan
$75 nightly
The price is $95
Nov 15 - Nov 16
Total with taxes and fees
I Parigi Corbinelli

8. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
$42 nightly
The price is $50
Nov 22 - Nov 23
Total with taxes and fees
hu Firenze Certosa camping in town

9. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
$127 nightly
The price is $148
Nov 15 - Nov 16
Total with taxes and fees
L' Eroico

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
$143 nightly
The price is $161
Nov 21 - Nov 22
Total with taxes and fees
La Locanda di Pietracupa

11. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$126 nightly
The price is $143
Nov 15 - Nov 16
Total with taxes and fees
Agriturismo La Ferrozzola

12. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 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
$117 nightly
The price is $131
Nov 16 - Nov 17
Total with taxes and fees
Casa Vacanze Squarcialupi

13. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
$101 nightly
The price is $113
Nov 16 - Nov 17
Total with taxes and fees
Relais Villa Belvedere

14. Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.2 out of 10, Wonderful, (15 reviews)
"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
$176 nightly
The price is $197
Nov 15 - Nov 16
Total with taxes and fees
Rocca Palazzaccio

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
$114 nightly
The price is $130
Nov 15 - Nov 16
Total with taxes and fees
B&B La Fonte del Machiavelli

16. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$94 nightly
The price is $104
Nov 15 - Nov 16
Total with taxes and fees
Villa Cassia di Baccano

17. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
$157 nightly
The price is $177
Nov 26 - Nov 27
Total with taxes and fees
Villa il Fedino

18. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
$158 nightly
The price is $174
Nov 15 - Nov 16
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca

19. Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (38 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
$73 nightly
The price is $83
Nov 20 - Nov 21
Total with taxes and fees
Residence Il Connubio

20. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (9 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
$126 nightly
The price is $131
Nov 15 - Nov 16
Total with taxes and fees
Old medieval apartment
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

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