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Holiday Rentals in Gaiole in Chianti

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The best holiday rentals in Gaiole in Chianti

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Agriturismo San Sano

Gaiole in Chianti

Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti.

C
Chih-Wei
From
Taiwan
Everything is great, beautiful and vintage house, room is comfortable, breakfast and parking space is good , the staff for checking are so warm and nice , and the staff girl for check out is amazing beautiful, and of course friendly. Btw, there are 2 cute cats there, I hope to come back soon.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,258 reviews
Price from
US$126.27
1 night, 2 adults

BORGO A MONTI di Sotto

Gaiole in Chianti

20 km from Piazza del Campo, BORGO A MONTI di Sotto is a recently renovated property located in Gaiole in Chianti and provides air-conditioned rooms with free WiFi and private parking.

J
Jonathan
From
Switzerland
We rented an apartment with two couples as we attended a wedding close by - the place was great in so many aspects, very spacious and freshly renovated apartments, nice pool, very calm with great view and super friendly and accommodating team.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 155 reviews
Price from
US$240.02
1 night, 2 adults

RICASOLI, Brolio Agriroom

Gaiole in Chianti

Offering a garden and garden view, RICASOLI, Brolio Agriroom is situated in Gaiole in Chianti, 23 km from Piazza del Campo and 35 km from Piazza Matteotti.

T
Thomas
From
United Kingdom
Unbelievable. One of the best places I have ever stayed in my life. Both the wine tour and the dinner were exceptional. The views from the castle onto the Tuscan countryside were unforgettable.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 255 reviews
Price from
US$140.38
1 night, 2 adults

Cavarchino B&B

Gaiole in Chianti

Featuring a garden and views of pool, Cavarchino B&B is a bed and breakfast situated in a historic building in Gaiole in Chianti, 30 km from Piazza Matteotti.

A
Ada
From
Luxembourg
Amazing place to stay in Giaole in Chianti. The staff was very welcoming and helpful, the room was very comfy and the breakfast delicious. I particularly liked the pool area which offered a beautiful view of the town.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 126 reviews
Price from
US$173.92
1 night, 2 adults

Capannelle Wine Resort

Gaiole in Chianti

Located on a hillside and surrounded by vineyards and cypress trees, Capanelle Wine Resort is around 500mt from Gaiole in Chianti's town centre.

V
Vjolla
From
Kosovo
We liked everything and really enjoyed our time there. The staff were very friendly and helpful. The view from the hotel is amazing. We did the wine tour paired with lunch and it was amazing. The rooms were clean and had everything we needed.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 204 reviews
Price from
US$427.28
1 night, 2 adults

Badia a Coltibuono Wine Resort

Gaiole in Chianti

Badia a Coltibuono, Abbey of 1051, is the first wine resort in Chianti that offers a truly exceptional experience.

T
Thorsten
From
Germany
My partner loves the pool. I love the historic bulidings, the garden / terrace with the breakfast outside. And it is a rare experience to stay in such an historic location.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 311 reviews
Price from
US$232.46
1 night, 2 adults

Casa Vacanze Chianti Summer

Gaiole in Chianti

Boasting air-conditioned accommodation with a private pool, Casa Vacanze Chianti Summer is situated in Gaiole in Chianti.

M
Mark
From
United Kingdom
We had the whole lower floor of the house with our own living room and kitchen as well as bathroom and bedroom. There is a swimming pool and outside table for breakfast in the sunshine. It is very well situated as it is a very short walk into the centre for restaurants and bars. There is also sheltered parking at the house
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 12 reviews
Price from
US$537.79
1 night, 2 adults

Podere Erbolino

Gaiole in Chianti

Located in Gaiole in Chianti in the Tuscany region, Podere Erbolino has a balcony. A hot tub is available for guests.

M
Mihaela
From
Romania
Our stay at Podere Erbolino was nothing short of magical. Nestled in the heart of Tuscany, this property exceeded every expectation we had for our Italian getaway.The house itself is absolutely stunning - a perfect blend of authentic Tuscan charm and modern comfort. Every detail has been thoughtfully considered, from the rustic stone walls to the beautifully appointed interiors that make you feel instantly at home. The accommodation exudes warmth and character that you simply can't find anywhere else.But what truly took our breath away was waking up each morning to the most spectacular view imaginable. The rolling hills of Tuscany stretched endlessly before us... It was like stepping into a Renaissance painting every single day - absolutely dreamlike and unforgettable. The location is perfect for exploring the Tuscan countryside while providing a peaceful retreat where you can truly disconnect and immerse yourself in the beauty of Italy. Whether you're sipping wine on the terrace at sunset or simply taking in the panoramic vistas, every moment feels special. Podere Erbolino isn't just accommodation - it's an experience that captures the very essence of what makes Tuscany so enchanting. We left with hearts full of beautiful memories and are already planning our return. Highly recommended for anyone seeking an authentic and truly amazing Tuscan escape.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 16 reviews
Price from
US$3,773.48
1 night, 2 adults

B&B L'Eroico

Gaiole in Chianti

Offering a garden and city view, B&B L'Eroico is set in Gaiole in Chianti, 30 km from Piazza Matteotti and 30 km from Piazza del Campo.

G
Giulia
From
United Kingdom
The venue is all new and decorated with taste. The beds are very comfortable and the breakfast is lovely. All home made biscuits and cakes, and cooked, savoury breakfast if wanted. Monica the owner is really friendly ad helpful. Bike storage with charging point for e-bikes was important to us and this was provided. 3 minutes away from lovely restaurants and cafes.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 82 reviews
Price from
US$181.81
1 night, 2 adults

La Loggetta - Apartments

Gaiole in Chianti

Set in Gaiole in Chianti and only 30 km from Piazza Matteotti, La Loggetta - Apartments offers accommodation with pool views, free WiFi and free private parking.

S
Stefan
From
Romania
Location, quiet atmosphere, very relaxing. Typical Tuscan accommodation.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 55 reviews
Price from
US$124.32
1 night, 2 adults
All holiday rentals in Gaiole in Chianti

Most booked holiday rentals in Gaiole in Chianti and surroundings in the past month

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Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 155 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 72 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 163 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 126 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 357 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 255 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 311 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 163 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,258 reviews

Popular with guests booking holiday rentals in Gaiole in Chianti

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 654 reviews

Enjoy breakfast in Gaiole in Chianti and nearby

Scored out of 10, guest rating 7.1
Good - What previous guests thought, 412 reviews

The Relais Santa Cristina is a renovated country house in the heart of the Chianti wine country, outside Siena. It offers panoramic views, an outdoor pool and free parking.

From US$140 per night

Le Lappe

Cavriglia
Breakfast options
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 209 reviews

Set in Cavriglia, 31 km from The Mall Luxury Outlet, Le Lappe offers accommodation with a hot tub and wellness packages. This farm stay features a pool with a view, a garden and free private parking.

From US$252.02 per night
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 114 reviews

Located just 38 km from Piazza Matteotti, Agriturismo La Forra features accommodation in Cavriglia with access to a bar, a shared lounge, as well as a concierge service.

From US$194.80 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 531 reviews

Featuring pool with a view and views of garden, Castello di Volpaia is a country house situated in a historic building in Radda in Chianti, 22 km from Piazza Matteotti.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 46 reviews

Located within 35 km of Piazza Matteotti and 44 km of Piazza del Campo in Cavriglia, Tenuta San Jacopo - Agriturismo provides accommodation with seating area.

From US$203.63 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 82 reviews

Offering a garden and city view, B&B L'Eroico is set in Gaiole in Chianti, 30 km from Piazza Matteotti and 30 km from Piazza del Campo.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Boasting air-conditioned accommodation with a private pool, Ciacchieri is situated in Gaiole in Chianti. This property offers access to a balcony, free private parking and free WiFi.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 4 reviews

Situated in Gaiole in Chianti, 27 km from Piazza Matteotti and 28 km from Piazza del Campo, Casa Ciaccheri offers air conditioning.

These holiday rentals in Gaiole in Chianti and nearby have options with free cancellation

Villino Chianti

Cavriglia
Free cancellation options available
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 31 reviews

Situated in Cavriglia, the recently renovated Villino Chianti features accommodation 30 km from The Mall Luxury Outlet and 36 km from Piazza Matteotti.

From US$157.69 per night

Il Nespolo

Cavriglia
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 78 reviews

Featuring air-conditioned accommodation with a terrace, Il Nespolo is set in Cavriglia. With garden views, this accommodation offers a balcony.

Castello di Selvole

Vagliagli
Free cancellation options available
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 58 reviews

Set in a historical hills of Chianti Classico, Castello di Selvole is a winery offering hospitality with an outdoor pool.

From US$162.33 per night

Casa Badia

Radda in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 87 reviews

Casa Badia has quiet street views, free WiFi and free private parking, situated in Radda in Chianti, 18 km from Piazza Matteotti.

From US$112.70 per night

Casa Ciaccheri 2

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 26 reviews

Located in Gaiole in Chianti, 30 km from Piazza Matteotti and 31 km from Piazza del Campo, Casa Ciaccheri 2 provides air-conditioned accommodation with a balcony and free WiFi.

Casa Marcella nel cuore del Chianti

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 13 reviews

Featuring garden views, Casa Marcella nel cuore del Chianti provides accommodation with a garden and a balcony, around 27 km from Piazza Matteotti.

Castelli del Chianti

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 72 reviews

Featuring garden views, Castelli del Chianti provides accommodation with balcony, around 29 km from Piazza Matteotti.

Il Balcone

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set in Gaiole in Chianti, 30 km from Piazza Matteotti and 31 km from Piazza del Campo, Il Balcone offers air-conditioned accommodation with a balcony and free WiFi.

Holiday Rentals with swimming pools in Gaiole in Chianti and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 7 reviews

Boasting accommodation with a private pool, Tuscan Countryside Paradise with Pool is located in Cavriglia. This property offers access to a balcony, free private parking and free WiFi.

From US$542.65 per night
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews

Featuring accommodation with a pool with a view, mountain view and a patio, Borgo di Gaiole - Casa BD - apartment with a view & travel guide is situated in Gaiole in Chianti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Situated in Gaiole in Chianti, Il Colombaio by VacaVilla features accommodation with private pool, free WiFi and free private parking for guests who drive.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 55 reviews

Set in Gaiole in Chianti and only 30 km from Piazza Matteotti, La Loggetta - Apartments offers accommodation with pool views, free WiFi and free private parking.

From US$140.55 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 204 reviews

Located on a hillside and surrounded by vineyards and cypress trees, Capanelle Wine Resort is around 500mt from Gaiole in Chianti's town centre.

From US$318.86 per night

Situated in Gaiole in Chianti, 28 km from Piazza Matteotti and 29 km from Piazza del Campo, Villa Radda by Mmega offers air conditioning.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 20 reviews

Located in Gaiole in Chianti, Casina provides accommodation with a private pool, a patio and mountain views. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 9 reviews

Featuring a garden, private pool and garden views, Il Molinaccio is set in Gaiole in Chianti. This property offers access to a patio, a pool table, free private parking and free WiFi.

Highly rated holiday rentals in Gaiole in Chianti and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 51 reviews

Set just 26 km from Piazza Matteotti, Casa Vacanze Vertine offers accommodation in Gaiole in Chianti with access to a spa and wellness centre, an open-air bath, as well as a 24-hour front desk.

From US$133.34 per night
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 63 reviews

Boasting quiet street views, Camere e Appartamenti Baldini Romanita provides accommodation with patio, around 18 km from Piazza Matteotti.

From US$115.95 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 126 reviews

Featuring a garden and views of pool, Cavarchino B&B is a bed and breakfast situated in a historic building in Gaiole in Chianti, 30 km from Piazza Matteotti.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 23 reviews

Set in Gaiole in Chianti and only 30 km from Piazza Matteotti, Agriturismo Vinci offers accommodation with lake views, free WiFi and free private parking.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews

Situated in Gaiole in Chianti and only 30 km from Piazza Matteotti, Montemarcoli features accommodation with mountain views, free WiFi and free private parking.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 163 reviews

Situated within 27 km of Piazza Matteotti and 28 km of Piazza del Campo, La Corte del Chianti Classico features rooms with air conditioning and a private bathroom in Gaiole in Chianti.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 8 reviews

Featuring air-conditioned accommodation with a terrace, Holiday Home Montechioccioli-2 by Interhome is set in Gaiole in Chianti. Guests staying at this holiday home have access to a balcony.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 158 reviews

Set within 30 km of Piazza Matteotti and 31 km of Piazza del Campo, Rietine24 offers rooms with air conditioning and a private bathroom in Gaiole in Chianti.

FAQ about holiday rentals in Gaiole in Chianti

Holiday rentals that guests love in Gaiole in Chianti

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Avg. price/night: US$169.34
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 654 reviews
I have been to this castle a lot of times and I love it. You instantly relax when you get arrive and the buildings and vibe is just lovely. There was 8 of us this time. Village nearby is lovely and it is a short drive to other places. Breakfast is lovely and there are two beautiful pools (Although they were covered in wasps!!)
Guest review by
Fiona
Group
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,258 reviews
Beautiful agriturismo in the Chianti area about half an hour from Siena. We loved everything about this agriturismo: the friendly welcome, the spacious and well-equipped room, the light dinner that the agriturismo offers, the beatuiful building and garden, and the location: San Sano. A very small, picturesque Tuscan village. We shall be back for sure!
Guest review by
Ulrike
Family with young children
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,258 reviews
This place is a little oasis where you can relax and enjoy the feeling of a tiny tuscan village and a huge wineyard. It is lucky that they dont upload new pictures of the property, otherwise they wouldnt have any vacancy :D Everything is covered with flowers, room and pool is clean, breakfast is really good with excellent background music, lot of things to see nearby. We also enjoyed the kind service of Lorena who is super sweet! We had the chance to meet with the owner and take a winetour which was really interesting.
Guest review by
Veronika
Young couple
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 1,258 reviews
Very friendly staff, with good breakfast and lunch/dinner options featuring local products and wine from their own winery. Everything was super clean, including the rooms and the pool area. It is a great small village for people who want to enjoy the nature and chill vibes of the Chianti area.
Guest review by
Mariya
Young couple
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 63 reviews
A beautiful and quiet Tuscany villa in the middle of olive groves and a very kind and hospitable host
Guest review by
Vladimír
Family with young children
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 158 reviews
Location (Chianti region, tiny village on a hill), characteristics of the room (design) and the very friendly and helpful owner.
Guest review by
maurice
Young couple
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 80 reviews
When we arrived at the accommodation, surrounded by a beautiful landscape, our hostess Jasmin welcomed us and showed us around the stunningly beautiful property. We immediately felt at home, which was mainly due to the great service and the extravagant interior design. The entire house is incredibly tastefully furnished and invites you to relax. The rooms are very comfortable and wonderfully equipped. We left the villa with a homemade peach cake and are already looking forward to our next visit!
Guest review by
Heinersdorff
Young couple
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 63 reviews
Very charming old Tuscan villa with a lot of space. There was a huge living room with lots of space. Nice Garden area with lots of seating space and grill station.
Guest review by
Christopher
Group
Avg. price/night: US$110.15
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 105 reviews
Alessandra was a delight! She was friendly, helpful with answering questions about the area and available for our needs. The room was beautiful comfortable and very clean. The grounds on property were beautiful, lush and green ,with flowers, olive trees and grapes. The location was peaceful and easy walking distance to little village. We got the breakfast which was extra but was well worth it. Alessandra set up our breakfast in the shared kitchen. We had espresso, fruit, yogurt and croissant. We enjoyed our visit and would stay here again.
Guest review by
Diana
Young couple