A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Gaiole in Chianti vacation rentals

Exterior

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 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
The price is SAR 550
SAR 640 total
includes taxes & fees
2 Aug - 3 Aug
L' Eroico
Exterior

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is SAR 688
SAR 791 total
includes taxes & fees
4 Aug - 5 Aug
Borgo Argenina
Lounge

3. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is SAR 318
SAR 367 total
includes taxes & fees
4 Aug - 5 Aug
Mariani Bed & Breakfast
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

4. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (37 reviews)
"Great spot"
Canada
Philippe
The price is SAR 644
SAR 709 total
includes taxes & fees
10 Aug - 11 Aug
Villa di Sotto
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

5. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is SAR 450
SAR 504 total
includes taxes & fees
18 Aug - 19 Aug
Borgo di Erboli
Aerial view

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is SAR 666
SAR 767 total
includes taxes & fees
5 Aug - 6 Aug
Villa Curina Resort
Exterior

7. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is SAR 313
SAR 362 total
includes taxes & fees
1 Aug - 2 Aug
Villa le Camelie Siena
Outdoor pool

8. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very Good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
Villa Rosa Panzano
Property grounds

9. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is SAR 255
SAR 297 total
includes taxes & fees
5 Aug - 6 Aug
Domus il Palio B&B
Exterior

10. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (328 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is SAR 350
SAR 398 total
includes taxes & fees
3 Aug - 4 Aug
Hu Norcenni Girasole Village
Free daily buffet breakfast

11. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is SAR 1,162
SAR 1,295 total
includes taxes & fees
2 Aug - 3 Aug
Terre di Baccio
City view from property

12. Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very Good, (17 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is SAR 311
SAR 359 total
includes taxes & fees
5 Aug - 6 Aug
Birbo Bike Hospitality
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

13. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is SAR 461
SAR 524 total
includes taxes & fees
30 Aug - 31 Aug
Residenzia del Sogno
Breakfast, lunch and dinner served

14. La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.6 out of 10, Exceptional, (38 reviews)
"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."
Australia
Con
The price is SAR 618
SAR 698 total
includes taxes & fees
1 Aug - 2 Aug
La Locanda di Pietracupa
Aerial view

15. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is SAR 842
SAR 935 total
includes taxes & fees
29 Aug - 30 Aug
Riserva di Fizzano Residence
View from room

16. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is SAR 391
SAR 439 total
includes taxes & fees
25 Aug - 26 Aug
Chianti Village Morrocco
Room amenity

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (468 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is SAR 471
SAR 535 total
includes taxes & fees
3 Aug - 4 Aug
Siena Vip
Panoramic Apartment (2) | Terrace/patio

18. 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
The price is SAR 484
SAR 558 total
includes taxes & fees
18 Aug - 19 Aug
Casa Vacanze Squarcialupi
Garden view

19. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is SAR 404
SAR 471 total
includes taxes & fees
31 Aug - 1 Sep
Villa San Filippo
Chalet | In-room safe, cribs (surcharge), bed sheets

20. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,710 reviews)
"Clean room and great proximity to town."
United States
KEVIN
The price is SAR 240
SAR 294 total
includes taxes & fees
30 Aug - 31 Aug
Hu Firenze Camping In Town
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 Gaiole in Chianti Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Really nice hotel! The gardens at the back of the property were a really nice surprise!"
Jerome 1-night trip
Posted 13 hours ago
La Certosa di Pontignano

Frequently asked questions

Can I find vacation rentals in Gaiole in Chianti?

Yes, we have vacation rentals close to the most popular attractions in Gaiole in Chianti, or you can choose a more secluded option if you're looking for relaxation. The spas and wineries are several reasons why visitors like Gaiole in Chianti. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Gaiole in Chianti has to offer?

Borgo Argiano: Visitors like this Gaiole in Chianti vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Gaiole in Chianti?

With 26 Expedia vacation rentals, you're sure to find just the right place for your Gaiole in Chianti stay.

What’s there to see and do in Gaiole in Chianti?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Chianti Sculpture Park. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

What’s a vacation rental in Gaiole in Chianti like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Gaiole in Chianti. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.