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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Gaiole in Chianti holiday rentals

Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"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
The price is ฿5,336
฿6,172 total
includes taxes & fees
11 May - 12 May
L' Eroico
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is ฿8,177
฿9,297 total
includes taxes & fees
23 Apr - 24 Apr
Borgo Argenina
Exterior

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28 reviews)
"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 ฿4,973
฿5,771 total
includes taxes & fees
22 Apr - 23 Apr
Rocca di Castagnoli
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is ฿49,845
฿54,980 total
includes taxes & fees
29 Apr - 30 Apr
Terre di Baccio
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿5,216
฿5,738 total
includes taxes & fees
18 May - 19 May
Villa Cassia di Baccano
View from property

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 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
The price is ฿4,115
฿5,432 total
includes taxes & fees
17 May - 18 May
Antica Pieve B&B
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (236 reviews)
"Wonderful stay- we really enjoyed our stay and did not want to leave!! Beautiful hotel and wonderful service!"
United States
Cameron
The price is ฿5,795
฿6,488 total
includes taxes & fees
20 Apr - 21 Apr
Relais Villa Olmo
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ฿3,434
฿3,928 total
includes taxes & fees
21 Apr - 22 Apr
Il Pozzo di Sant'Andrea
Property grounds

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is ฿7,851
฿8,787 total
includes taxes & fees
18 Apr - 19 Apr
Ca' Bianca Tuscany Relais
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ฿4,072
฿4,630 total
includes taxes & fees
19 Apr - 20 Apr
B&B La Fonte del Machiavelli
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (29 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is ฿5,222
฿5,744 total
includes taxes & fees
19 Apr - 20 Apr
Villa di Sotto
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ฿6,740
฿7,565 total
includes taxes & fees
19 Apr - 20 Apr
Villa il Fedino
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is ฿6,635
฿7,374 total
includes taxes & fees
13 May - 14 May
Riserva di Fizzano Residence
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is ฿7,590
฿8,462 total
includes taxes & fees
21 Apr - 22 Apr
Luxury resort in the Tuscan countryside
Food court

Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is ฿5,710
฿6,394 total
includes taxes & fees
17 May - 18 May
Antico Borgo Poggiarello
Garden

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
The price is ฿2,938
฿3,383 total
includes taxes & fees
16 May - 17 May
Villa Cristina
Pool

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is ฿27,777
฿30,857 total
includes taxes & fees
18 Apr - 19 Apr
Villa Marcolina
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ฿2,846
฿3,358 total
includes taxes & fees
4 May - 5 May
iConic Wellness Resort
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ฿8,145
฿9,110 total
includes taxes & fees
4 May - 5 May
Castello di Gargonza
Front of property

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is ฿5,787
฿6,667 total
includes taxes & fees
27 Apr - 28 Apr
Villa Curina Resort
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

4/10 Poor
"We had booked a 2 bedroom apartment. Was given a 3 bedroom with extremely short ceiling in the bedrooms. Only 1 bathroom that was about 5ftx5ft. The door to the bathroom was about 5 7ft so my husband could not get in without bending. Staff were rude and just horrible. Not accommodative at all. "
Mina 6-night trip
Posted 7 hours ago
La Certosa di Pontignano

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:

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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 an espresso maker. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 28 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. Medieval Tower of Barbischio and Meleto Castle 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.