View over the hills from the Brolio Castle

Gaiole in Chianti Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Gaiole in Chianti holiday rentals

Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is HK$2,466
HK$2,784 total
includes taxes & fees
18 Jun - 19 Jun
Borgo Argenina
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 HK$1,178
HK$1,368 total
includes taxes & fees
9 Jul - 10 Jul
L' Eroico
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 HK$894
HK$984 total
includes taxes & fees
25 Jun - 26 Jun
Villa Cassia di Baccano
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 HK$2,254
HK$2,516 total
includes taxes & fees
12 Jul - 13 Jul
Villa il Fedino
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 HK$1,053
HK$1,195 total
includes taxes & fees
12 Jun - 13 Jun
B&B La Fonte del Machiavelli
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is HK$1,785
HK$1,982 total
includes taxes & fees
15 Jun - 16 Jun
Riserva di Fizzano Residence
Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is HK$1,496
HK$1,673 total
includes taxes & fees
16 Jun - 17 Jun
Villa Montecastello
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is HK$1,951
HK$2,182 total
includes taxes & fees
12 Jun - 13 Jun
Castello di Gargonza
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is HK$1,265
HK$1,428 total
includes taxes & fees
22 Jun - 23 Jun
La Coroncina Lodging
8 outdoor pools

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is HK$6,658
HK$7,396 total
includes taxes & fees
12 Jun - 13 Jun
Villa Marcolina
Premium bedding, down duvets, pillow-top beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$599
HK$776 total
includes taxes & fees
14 Jun - 15 Jun
Tuscasì Aparthotel
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is HK$1,251
HK$1,376 total
includes taxes & fees
18 Jun - 19 Jun
Villa di Sotto
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is HK$2,923
HK$3,234 total
includes taxes & fees
12 Jul - 13 Jul
Fontelunga Hotel & Villas
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 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 HK$2,461
HK$2,744 total
includes taxes & fees
15 Jun - 16 Jun
Terre di Baccio
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is HK$2,308
HK$2,593 total
includes taxes & fees
15 Jun - 16 Jun
2 Cuori e 1 Yurta Glamping in Toscana
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is HK$632
HK$741 total
includes taxes & fees
24 Jun - 25 Jun
RESIDENCE LECCIO
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 HK$871
HK$994 total
includes taxes & fees
14 Jun - 15 Jun
Il Pozzo di Sant'Andrea
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (172 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is HK$904
HK$1,067 total
includes taxes & fees
24 Jun - 25 Jun
Bosco della Spina
Seasonal outdoor pool, pool umbrellas, pool loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
The price is HK$586
HK$699 total
includes taxes & fees
15 Jun - 16 Jun
Villa San Filippo
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.6 out of 10, Exceptional, (204 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is HK$827
HK$946 total
includes taxes & fees
3 Jul - 4 Jul
B&B Il Corso
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

8/10 Good
"It's nice to be surrounded by plants than just city"
Ky 3-night trip
Posted 10 hours ago
Hu Firenze Camping In Town

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 electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Gaiole in Chianti?

With 22 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 Chianti Sculpture Park. 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.