Chianti Region Vacation Rentals

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Check prices for these dates

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, (275 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
$91 nightly
The price is $103
Nov 23 - Nov 24
Total with taxes and fees
Relais Villa Olmo - Place of Charme

2. 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.
$128 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Old medieval apartment

3. 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
$72 nightly
The price is $81
Dec 5 - Dec 6
Total with taxes and fees
Chianti Village Morrocco

4. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$119 nightly
The price is $136
Nov 9 - Nov 10
Total with taxes and fees
Agriturismo La Ferrozzola

5. 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
$107 nightly
The price is $122
Dec 1 - Dec 2
Total with taxes and fees
Antica Pieve B&B

6. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
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
$163 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

7. 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
$97 nightly
The price is $108
Nov 7 - Nov 8
Total with taxes and fees
Relais Villa Belvedere

8. 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
$160 nightly
The price is $180
Nov 23 - Nov 24
Total with taxes and fees
Villa il Fedino

9. 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
$260 nightly
The price is $290
Nov 9 - Nov 10
Total with taxes and fees
Terre di Baccio

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
$145 nightly
The price is $164
Nov 8 - Nov 9
Total with taxes and fees
La Locanda di Pietracupa

11. 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 9 - Nov 10
Total with taxes and fees
Casa Vacanze Squarcialupi

12. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$118 nightly
The price is $132
Dec 3 - Dec 4
Total with taxes and fees
Palazzo Pacini

13. 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
$129 nightly
The price is $151
Nov 6 - Nov 7
Total with taxes and fees
L' Eroico

14. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
$76 nightly
The price is $97
Nov 11 - Nov 12
Total with taxes and fees
I Parigi Corbinelli

15. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (125 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
$42 nightly
The price is $50
Nov 17 - Nov 18
Total with taxes and fees
hu Firenze Certosa camping in town

16. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
Teranga in Chianti - Parking & Garden 3 BR

17. 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
$116 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
B&B La Fonte del Machiavelli

18. 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
$179 nightly
The price is $200
Nov 10 - Nov 11
Total with taxes and fees
Rocca Palazzaccio

19. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
9.6 out of 10, Exceptional, (5 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
$89 nightly
The price is $102
Nov 12 - Nov 13
Total with taxes and fees
Borgo Antico Residence

20. 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
$96 nightly
The price is $106
Nov 6 - Nov 7
Total with taxes and fees
Villa Cassia di Baccano
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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