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

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Gaiole in Chianti villas

Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is AU$1,218
includes taxes & fees
24 July - 25 July
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Outdoor dining

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveller
The price is AU$2,101
includes taxes & fees
25 July - 26 July
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is AU$1,294
includes taxes & fees
18 July - 19 July
Villa Marcolina
Exterior

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is AU$1,375
includes taxes & fees
19 July - 20 July
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AU$303
includes taxes & fees
19 July - 20 July
Villa Montecastello
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful property and great experience "
United States
edward p.
The price is AU$535
includes taxes & fees
19 July - 20 July
Luxury Villa in the Florentine hills
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is AU$816
includes taxes & fees
19 July - 20 July
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is AU$999
includes taxes & fees
19 July - 20 July
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Outdoor dining

Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AU$2,890
includes taxes & fees
18 July - 19 July
Villa Capanna: A Window onto Tuscany
Outdoor dining

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...
Germany
Anonymous traveller
The price is AU$791
includes taxes & fees
24 July - 25 July
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is AU$689
includes taxes & fees
19 July - 20 July
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is AU$1,645
includes taxes & fees
20 July - 21 July
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AU$199
includes taxes & fees
19 July - 20 July
Rooster House, cooking classes and opera
Exterior

La Dimora di Teresa: fairytale house in the woods, ideal for families with children.

La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
Sovicille
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful house for our family. Spacious and well appointed home with a charming rustic feel. It is a short drive to Siena. Marina is super helpful with any need you may have. We had a local chef come to the house to make pizzas for us one evening. It was terrific. Our family enjoyed the peace and quiet of this home in the middle of a busy trip around Italy."
United States
Ericka B.
The price is AU$1,426
includes taxes & fees
23 July - 24 July
La Dimora di Teresa: fairytale house in the woods, ideal for families with children.
Exterior

Romantic stylish villa with private pool & splendid view

Romantic stylish villa with private pool & splendid view
Panzano In Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful location with spectacular views."
United States
lawrence s.
The price is AU$1,824
includes taxes & fees
30 July - 31 July
Romantic stylish villa with private pool & splendid view
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is AU$1,603
includes taxes & fees
19 July - 20 July
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is AU$741
includes taxes & fees
19 July - 20 July
Villa Il Signorino
Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (68 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
Il Poggio dell'Eremita
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AU$4,975
includes taxes & fees
7 Aug - 8 Aug
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Casale Le Rondini with a swimming pool and private garden

Casale Le Rondini with a swimming pool and private garden
LUCIGNANO
Casale Le Rondini with a swimming pool and private garden
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Gorgeous hotel, amazing views. Fabulous staff. They made our stay in Siena extra special."
Seth 2-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
264
Accommodation
1592 Villas
Lowest Price
AU$199
Highest Price
AU$4,975

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Expect to pay between AU$199 and AU$4,975 per night for villas in Gaiole in Chianti. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Gaiole in Chianti?
Pick from 1592 villas in Gaiole in Chianti. Whether you're travelling with the little ones or planning a getaway with some friends, Expedia can help you find the best space for your crew.
What is there to do near my villa in Gaiole in Chianti?
Whatever your tastes or interests, Gaiole in Chianti has loads to keep you entertained. Castle of Brolio, Meleto Castle and Castello di Radda Winery are on most visitors' sightseeing plans. Don't head home without exploring Castello di Albola, Badia a Coltibuono and Il Molino di Grace Winery either. With Expedia's hotel deals in Gaiole in Chianti, you can see more terrific attractions like these with the cash you save.