The 10 best vacation rentals in Gaiole in Chianti, Italy | Booking.com
Skip to main content

Vacation Rentals in Gaiole in Chianti

Find the vacation rentals that appeal to you the most

Vacation Rentals for every style

Find the right vacation rental for you in Gaiole in Chianti

The best vacation rentals in Gaiole in Chianti

Check out our selection of great vacation rentals in Gaiole in Chianti

Filter by:

Review score

BORGO A MONTI di Sotto

Gaiole in Chianti

12 miles from Piazza del Campo in Gaiole in Chianti, BORGO A MONTI di Sotto offers accommodations with access to a public bath and open-air bath.

E
Edna
From
Germany
The atmosphere, the cleanliness, and Rosa was very accommodating. Great place to stay.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 145 reviews
Price from
$242.02
1 night, 2 adults

Cavarchino B&B

Gaiole in Chianti

Cavarchino B&B offers accommodations in Gaiole in Chianti, 19 miles from Piazza Matteotti and 19 miles from Piazza del Campo. Guests may go for a swim in the pool with a view.

A
Ana Patricia
From
Colombia
Beautiful house. Very confortable and clean rooms and bathrooms. Delicious Breakfast also. The staff so kind and helpful.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 141 reviews
Price from
$175.38
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.

J
Jose-Filipe
From
Portugal
It combines the beauty of nature and of historic places with the comfort of modern days. Definitely a place to rest and to appreciate nature. Our room was grand but at same time simple and comfortable. Homemade tasty food following old recipes. Staff are so genuine and so kind that you absolutely feel at home. Definitely a place to come back.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 306 reviews
Price from
$234.40
1 night, 2 adults

Casa Vacanze Chianti Summer

Gaiole in Chianti

Casa Vacanze Chianti Summer is located in Gaiole in Chianti, just 19 miles from Piazza del Campo and 23 miles from The Mall Luxury Outlet.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 11 reviews
Price from
$542.29
1 night, 2 adults

Podere Erbolino

Gaiole in Chianti

16 miles from Piazza Matteotti in Gaiole in Chianti, Podere Erbolino offers accommodations with access to a hot tub.

K
Krasavitsa Dina
From
Romania
Exceptional view at Toscana hills The property is clean, it has an amazing design and attention to every detail. The perfect mix of traditional and modern for a pleasant stay. The location is great as well. Very close to other wineries and castles. We will definitely come back to enjoy the vacation under the Tuscan sun.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 17 reviews
Price from
$1,162.03
1 night, 2 adults

Tenuta Di San Giusto in Salcio

Gaiole in Chianti

Tenuta Di San Giusto in Salcio offers an outdoor swimming pool and an open-air bath, as well as accommodations with a kitchen in Gaiole in Chianti, 13 miles from Piazza Matteotti.

m
maria
From
United States
The property was so beautiful. We loved learning about the history and restoration of the place.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 73 reviews
Price from
$2,338.40
1 night, 2 adults

B&B L'Eroico

Gaiole in Chianti

B&B L'Eroico offers accommodations in Gaiole in Chianti, 19 miles from Piazza del Campo and 24 miles from The Mall Luxury Outlet.

D
Duane
From
United States
The B&B was clean, comfortable, nicely decorated and Monica was a lovely hostess! Her breakfasts were a delicious start to the day. Gaiole is a quaint little town in beautiful Tuscany. We would absolutely stay there again.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 83 reviews
Price from
$183.33
1 night, 2 adults

RICASOLI, Brolio Agriroom

Gaiole in Chianti

RICASOLI, Brolio Agriroom offers air-conditioned accommodations in Gaiole in Chianti. Both free Wifi and parking on-site are accessible at the farm stay free of charge.

G
Guy
From
Netherlands
An excellent place the stay if you want to explore Castello di Brolio, eat at their Osteria, or taste Ricasoli wines across the street. The bedding was of high quality.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 256 reviews
Price from
$165.15
1 night, 2 adults

Agriturismo "Crocino in Chianti"

Gaiole in Chianti

16 miles from Piazza del Campo in Gaiole in Chianti, Agriturismo "Crocino in Chianti" features accommodations with access to a fitness room.

D
Diana
From
United States
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.
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 106 reviews
Price from
$111.07
1 night, 2 adults

Castello Di Meleto

Gaiole in Chianti

18 miles from Piazza Matteotti in Gaiole in Chianti, Castello Di Meleto provides accommodations with access to an open-air bath.

J
Justin
From
Netherlands
We loved our spacious little apartment with a view over the valley. The infinity pool was a lovely place to relax and cool off in the summer heat. The staff were all friendly and helpful and we enjoyed the tour of the castle with wine tasting at the end.
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 683 reviews
Price from
$170.63
1 night, 2 adults
All vacation rentals in Gaiole in Chianti

Most booked vacation rentals in Gaiole in Chianti and surrounding area in the past month

See all

Enjoy breakfast in Gaiole in Chianti and nearby

  • 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 $141.17 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 9 reviews

    B&B Borgolecchi, Lecchi in Chianti offers accommodations in San Sano, 16 miles from Piazza Matteotti and 29 miles from The Mall Luxury Outlet.

  • Le Lappe

    Cavriglia
    Breakfast options
    Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 206 reviews

    Le Lappe features a hot tub and wellness packages, as well as air-conditioned accommodations in Cavriglia, 19 miles from The Mall Luxury Outlet.

    From $341.52 per night
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 124 reviews

    19 miles from The Mall Luxury Outlet in Cavriglia, Agriturismo La Forra offers accommodations with access to a fitness room.

    From $184.15 per night
  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 195 reviews

    Tenuta Cortedomina features air-conditioned rooms in Radda in Chianti. 11 miles from Piazza Matteotti and 23 miles from Piazza del Campo, the property provides a garden and a shared lounge.

    From $307.50 per night
  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 541 reviews

    Providing garden views, Castello di Volpaia in Radda in Chianti provides accommodations, pool with a view, a garden, a bar, and barbecue facilities.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 596 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.

    From $437.28 per night
  • Borgo Carpineto

    Vagliagli
    Breakfast options
    Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 510 reviews

    Borgo Carpineto features a hot tub and free private parking, and is within 10 miles of Piazza del Campo and 18 miles of Piazza Matteotti.

    From $105.23 per night

Highly rated vacation rentals in Gaiole in Chianti and nearby

  • Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 62 reviews

    Camere e Appartamenti Baldini Romanita in Radda in Chianti provides accommodations with a garden and a terrace. Featuring mountain and lake views, this bed and breakfast also features free Wifi.

    From $111.07 per night
  • Scored out of 10, guest rating 9.4
    Wonderful - What previous guests thought, 60 reviews

    Offering mountain views, Agriturismo Borgo Il Bonagino in Radda in Chianti offers accommodations, pool with a view, a garden, and barbecue facilities.

    From $385.84 per night
  • Villino Chianti

    Cavriglia
    8.0+ review score
    Scored out of 10, guest rating 8.5
    Very Good - What previous guests thought, 32 reviews

    A recently renovated apartment, Villino Chianti offers accommodations in Cavriglia. Both free Wifi and parking on-site are accessible at the apartment free of charge.

    From $159.01 per night
  • L' Antico Comune

    Cavriglia
    8.0+ review score
    Scored out of 10, guest rating 8.0
    Very Good - What previous guests thought, 91 reviews

    L' Antico Comune offers accommodations in Cavriglia, 16 miles from The Mall Luxury Outlet and 20 miles from Piazza Matteotti. This apartment offers a shared lounge.

    From $81.84 per night
  • Il Nespolo

    Cavriglia
    8.0+ review score
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 78 reviews

    Offering a garden, Il Nespolo provides accommodations in Cavriglia. With garden views, this accommodation features a balcony.

    From $184.15 per night
  • Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 97 reviews

    Offering a garden, La Locanda Cuccuini provides accommodations in Cavriglia. This farm stay offers free private parking and luggage storage space.

    From $146.15 per night
  • Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 46 reviews

    Tenuta San Jacopo - Agriturismo provides a solarium and air-conditioned accommodations in Cavriglia, 20 miles from The Mall Luxury Outlet.

    From $173.50 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 80 reviews

    Casa Badia enjoys a location in Radda in Chianti, 11 miles from Piazza Matteotti and 17 miles from The Mall Luxury Outlet. Both Wifi and private parking are accessible at the apartment free of charge.

    From $108.38 per night

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

  • Chiantissima, Tuscany

    Starda
    Free cancellation options available
    Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 10 reviews

    Housed in a historic building, the recently renovated Chiantissima, Tuscany provides accommodations with a garden and free Wifi.

    From $175.56 per night
  • Castello di Selvole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 53 reviews

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

    From $133.29 per night
  • Agriturismo Oliviera Winery

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 524 reviews

    Providing a garden, Agriturismo Oliviera Winery offers accommodations in Vagliagli. This property offers access to a terrace, free private parking, and free Wifi.

  • Ciacchieri

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Ciacchieri is located in Gaiole in Chianti, just 19 miles from Piazza Matteotti and 19 miles from Piazza del Campo. This property offers access to a balcony, free private parking, and free Wifi.

  • Casa Ciaccheri 2

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 27 reviews

    Casa Ciaccheri 2 offers accommodations in Gaiole in Chianti, 19 miles from Piazza Matteotti and 19 miles from Piazza del Campo.

  • Casa Vacanze Chianti Summer

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 11 reviews

    Casa Vacanze Chianti Summer is located in Gaiole in Chianti, just 19 miles from Piazza del Campo and 23 miles from The Mall Luxury Outlet.

    From $645.57 per night
  • Casa Marcella nel cuore del Chianti

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 14 reviews

    Featuring a garden, Casa Marcella nel cuore del Chianti provides accommodations in Gaiole in Chianti. Both free Wifi and parking on-site are available at the apartment free of charge.

  • Castelli del Chianti

    Gaiole in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 64 reviews

    Castelli del Chianti offers accommodations in Gaiole in Chianti, 18 miles from Piazza Matteotti and 19 miles from Piazza del Campo.

FAQ about vacation rentals in Gaiole in Chianti

Vacation Rentals That Guests Love in Gaiole in Chianti

See all
  • Avg. price/night: $258.16
    Scored out of 10, guest rating 8.7
    Excellent - 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
  • Avg. price/night: $139.13
    Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 1,235 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
  • Avg. price/night: $139.13
    Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 1,235 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
  • Avg. price/night: $139.13
    Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 1,235 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, 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
  • Scored out of 10, guest rating 9.4
    Wonderful - What previous guests thought, 73 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: $111.07
    Scored out of 10, guest rating 8.4
    Very Good - What previous guests thought, 106 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