The 10 best holiday rentals in Gaiole in Chianti, Italy | Booking.com
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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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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.

P
Paul
From
New Zealand
Staff were very helpful and obliging. Lovely extra touches with breakfast offerings and bottle of wine. Assisted us with meal reservations and recommendations. Highly recommend. Pool area lovely.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 147 reviews
Price from
US$243.03
1 night, 2 adults
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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.

L
Leigh
From
United Kingdom
Lovely location, easy check in. The pool was AMAZING. Clean and neat. Fresh towels. Breakfast was awesome. Comfortable bed. Air conditioning if needed.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 140 reviews
Price from
US$176.11
1 night, 2 adults
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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.

A
Aidana
From
United States
We did the cooking class, which was amazing! Great experience. We had a great chef and met some wonderful people also participated in the class. The grounds were beautiful! We missed the official tours, but we asked the staff to get a look at the wine cellar and they were able to accommodate us for a quick visit. 10/10 stay and we’d highly recommend it to our friends.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 308 reviews
Price from
US$235.37
1 night, 2 adults
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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, 11 reviews
Price from
US$544.54
1 night, 2 adults
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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, 19 reviews
Price from
US$4,148.80
1 night, 2 adults
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Tenuta Di San Giusto in Salcio

Gaiole in Chianti

Featuring an open-air bath and views of garden, Tenuta Di San Giusto in Salcio is a homestay set in a historic building in Gaiole in Chianti, 21 km from Piazza Matteotti.

D
Deb
From
Australia
Amazing location and accommodation . Fabulous owners
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 76 reviews
Price from
US$2,348.10
1 night, 2 adults
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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.

j
jaguiar
From
France
Monica is a wonderful host (and chef 👩🏻‍🍳). She was always nice and helpful. She recommended a lot of good restaurants. She cooks incredible cakes for breakfast, and it was great to start the day. We asked her if she could also cook dinner for us one evening as it was a service offered in the flyer and we had a great time. Even the kids who are sometimes picky-eaters really enjoyed it. The rooms are very clean and comfortable, well arranged. You should definitely go there if you stay in the area! Thank you again for everything :-)
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 83 reviews
Price from
US$184.09
1 night, 2 adults
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Agriturismo "Crocino in Chianti"

Gaiole in Chianti

Offering pool views, Agriturismo "Crocino in Chianti" is an accommodation located in Gaiole in Chianti, 26 km from Piazza del Campo and 27 km from Piazza Matteotti.

A
Anita
From
Australia
Our host was so friendly and accommodating..such a wonderful place … will definitely come back Il nostro ospite è stato così gentile e disponibile… un posto davvero meraviglioso… torneremo sicuramente
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 107 reviews
Price from
US$111.53
1 night, 2 adults
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Castello Di Meleto

Gaiole in Chianti

Offering an open-air bath and garden view, Castello Di Meleto is set in Gaiole in Chianti, 29 km from Piazza Matteotti and 30 km from Piazza del Campo.

A
Ana Beatriz
From
El Salvador
One the most amazing places I have ever been to. My Husband and I visited the castle for our Honey Moon and it was just the cherry on top for our whole Italy trip. You have amazing views of the Tuscan Region, the smell of lavender, I felt pretty much royal staying there.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 680 reviews
Price from
US$171.34
1 night, 2 adults
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Borgo Casa al Vento

Gaiole in Chianti

Borgo Casa Al Vento is in the Tuscan countryside, 3 km from Gaiole In Chianti. It offers sport activities and a panoramic pool.

J
Joel
From
Australia
After reading some questionable reviews, we were pleasantly surprised at how beautiful this accomodation was. Our room itself was large, clean, air conditioned and what appeared like a newly renovated bathroom. The room was cleaned daily. While some fixtures are clearly older than others, it was part of the charm. They had great options for experiences hosted on site which allowed us to experience all we had hoped for by staying in the gorgeous Tuscan countryside. We personally loved the BBQ hosted on the Friday night which was a surprising touch. The food was amazing, accompanied by a beautiful bottle of their wine and live music. The wine tasting and cooking class were also great. Pool area was clean and great spot for relaxing. We are from Australia and would go out of our way to come back to this beautiful accomodation.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 360 reviews
Price from
US$221.64
1 night, 2 adults
Check availability
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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These holiday rentals in Gaiole in Chianti and nearby have options with free cancellation

  • Chianti chic

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 47 reviews

    Located in Gaiole in Chianti, 27 km from Piazza Matteotti and 28 km from Piazza del Campo, Chianti chic offers air conditioning.

    From US$228.94 per night

  • Relais Santa Cristina

    Radda in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 416 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$141.75 per night

  • Le Lappe

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 206 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$336.19 per night

  • Agriturismo La Forra

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 122 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$184.91 per night

  • Villino Chianti

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 32 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$159.67 per night

  • Castello di Volpaia

    Radda in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 543 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.

    From US$307.37 per night

  • Il Nespolo

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 79 reviews

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

    From US$184.91 per night

  • Wine Resort Dievole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 594 reviews

    Set in 600 hectares of beautiful Chianti countryside 20 minutes from Siena, Wine Resort Dievole offers different types of recently renovated apartment-suites and rooms in a large complex.

Enjoy breakfast in Gaiole in Chianti and nearby

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 192 reviews

    Set within 18 km of Piazza Matteotti and 36 km of Piazza del Campo, Tenuta Cortedomina features rooms with air conditioning and a private bathroom in Radda in Chianti.

    From US$369.83 per night

  • Borgo Carpineto

    Vagliagli
    Breakfast options
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 511 reviews

    Borgo Carpineto features a hot tub and free private parking, and is within 16 km of Piazza del Campo and 30 km of Piazza Matteotti.

    From US$105.66 per night
  • 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$174.22 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 516 reviews

    Featuring a garden, Agriturismo Oliviera Winery is located in Vagliagli in the Tuscany region, 13 km from Piazza del Campo and 30 km from Piazza Matteotti.

    From US$135.52 per night
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 83 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.

    From US$184.09 per night
  • Scored out of 10, guest rating 10.0
    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 9.5
    Exceptional - What previous guests thought, 27 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.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 14 reviews

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

Highly rated holiday rentals in Gaiole in Chianti and nearby

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 59 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$135.02 per night
  • Scored out of 10, guest rating 8.0
    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$111.53 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 80 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$108.83 per night
  • 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.

  • 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 8.4
    Very good - What previous guests thought, 58 reviews

    Boasting garden views, Guest House Sofia Villas provides accommodation with a garden, a terrace and barbecue facilities, around 30 km from Piazza Matteotti.

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 60 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.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 213 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.

FAQ about holiday rentals in Gaiole in Chianti

Holiday rentals that guests love in Gaiole in Chianti

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  • Castello Di Meleto

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$259.23
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 680 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

  • Agriturismo San Sano

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$127.97
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,238 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

  • Agriturismo San Sano

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$127.97
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,238 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

  • Agriturismo San Sano

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$127.97
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,238 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

  • Podere Lucignano Secondo Agriturismo

    Holiday Rental in Gaiole in Chianti
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 64 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

  • Rietine24

    Holiday Rental in Gaiole in Chianti
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 157 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

  • Tenuta Di San Giusto in Salcio

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$2,348.10
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 76 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

  • Podere Lucignano Secondo Agriturismo

    Holiday Rental in Gaiole in Chianti
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 64 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

  • Agriturismo "Crocino in Chianti"

    Holiday Rental in Gaiole in Chianti
    Avg. price/night: US$111.53
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 107 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