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

Gaiole in Chianti Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Gaiole in Chianti holiday rentals

A stone building with a yellow sign reading "b&b erioico".

1. 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
The price is HK$1,005
HK$1,176 total
includes taxes & fees
14 Nov - 15 Nov
L' Eroico
A stone building with a garden in front.

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is HK$1,470
HK$1,687 total
includes taxes & fees
31 Oct - 1 Nov
Borgo Argenina
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is HK$1,284
HK$1,413 total
includes taxes & fees
29 Oct - 30 Oct
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

4. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is HK$1,145
HK$1,294 total
includes taxes & fees
29 Oct - 30 Oct
Villa Curina Resort
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. 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
The price is HK$2,114
HK$2,360 total
includes taxes & fees
13 Nov - 14 Nov
Terre di Baccio
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

6. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (224 reviews)
"Very nice hotel with wonderful staff. Very accommodating. Would highly recommend."
United States
Anthony
The price is HK$871
HK$993 total
includes taxes & fees
9 Nov - 10 Nov
Il Battistero Siena - Residenza d'Epoca
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is HK$1,032
HK$1,170 total
includes taxes & fees
2 Nov - 3 Nov
Residenzia del Sogno
A table set with breakfast items on a balcony overlooking a historic town.

8. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (135 reviews)
"We had a great stay!"
United States
Suelina
The price is HK$1,190
HK$1,344 total
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

9. 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
The price is HK$1,164
HK$1,298 total
includes taxes & fees
2 Nov - 3 Nov
Palazzo Pacini
A table with two wine glasses, a bottle, and a book.

10. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (101 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is HK$543
HK$632 total
includes taxes & fees
18 Nov - 19 Nov
Domus il Palio B&B
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

11. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (60 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is HK$844
HK$964 total
includes taxes & fees
11 Nov - 12 Nov
Guild Living Siena Senior Resort & Residence
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

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
The price is HK$943
HK$1,089 total
includes taxes & fees
6 Nov - 7 Nov
Casa Vacanze Squarcialupi
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

13. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is HK$817
HK$925 total
includes taxes & fees
17 Nov - 18 Nov
Relais Villa Olmo - Place of Charme
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

14. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (254 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
La Terrazza Sul Campo Rooming House
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

15. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$484
HK$646 total
includes taxes & fees
20 Nov - 21 Nov
Tuscasì Aparthotel
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

16. 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
The price is HK$1,262
HK$1,388 total
includes taxes & fees
1 Nov - 2 Nov
Relais Villa Belpoggio - Residenza d'Epoca
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

17. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is HK$1,409
HK$1,585 total
includes taxes & fees
11 Nov - 12 Nov
PALAZZO DEL PAPA
A historic building with arched windows and a prominent entrance.

18. Casa Ciseri

Casa Ciseri
Siena City Centre
10.0 out of 10, Exceptional, (14 reviews)
"The property is beautiful and location excellent"
United States
Tania
The price is HK$1,238
HK$1,397 total
includes taxes & fees
4 Nov - 5 Nov
Casa Ciseri
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

19. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (76 reviews)
"Wonderful place, great location."
United States
Khaled
The price is HK$798
HK$913 total
includes taxes & fees
11 Nov - 12 Nov
B&B Palazzo del Magnifico
A bathroom with a window view of a historic building and a tiled roof.

20. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (495 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is HK$781
HK$894 total
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gaiole in Chianti Hotel Reviews

Italiana Hotels Florence

Italiana Hotels Florence

8/10 Good
"Breakfast and room was great. Swimming pool was closed during our stay. Carpet floor was smelling as it was wet. The location was not central from the main attractions. It took forever via public transport to reach to a hotel as Florence public transportation is the worst and didn’t go well after 6PM."
Gurpreet Singh 3-night trip
Posted 7 hours ago
Italiana Hotels Florence

Find out more about Gaiole in Chianti

Search for holiday rentals in Gaiole in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Gaiole in Chianti using one of the methods below:

  • View our selection of featured holiday rentals in Gaiole in Chianti
  • Use the map to find apartments and other holiday homes in the Gaiole in Chianti neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Gaiole in Chianti while they last

Look no further and take a look at our great range of rental properties in Gaiole in Chianti!

Frequently asked questions

Can I find holiday rentals in Gaiole in Chianti?

Yes, there are holiday rentals close to the most popular sights in Gaiole in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Gaiole in Chianti has to offer?

Borgo Argiano: This holiday home rental outside of Gaiole in Chianti is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 18 Expedia holiday rentals, you're guaranteed 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 Terme Antica Querciolaia. Meleto Castle and Badia a Coltibuono are other places to visit while you're in town.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gaiole in Chianti. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.