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

Check out our pick of great 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$228.41 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, 421 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$141.43 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$335.42 per night
  • Agriturismo La Forra

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 123 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$184.49 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$159.30 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$306.66 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$184.49 per night
  • Wine Resort Dievole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 595 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.

Highly rated holiday rentals in Gaiole in Chianti and nearby

  • 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$111.28 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 194 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$368.98 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, a property with a shared lounge, is situated in Cavriglia, 32 km from Piazza Matteotti, 43 km from Piazza del Campo, as well as 46 km from Piazza Grande.

    From US$81.99 per night
  • Borgo Carpineto

    Vagliagli
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 512 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$105.42 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$173.82 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$108.58 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 519 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$135.21 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.

Enjoy breakfast in Gaiole in Chianti and nearby

  • 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 9.5
    Exceptional - What previous guests thought, 11 reviews

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

    From US$646.76 per night
  • 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.

  • Scored out of 10, guest rating 10.0
    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.

  • 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 10.0
    Exceptional - What previous guests thought, 2 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.

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$258.63
    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
  • Avg. price/night: US$127.68
    Scored out of 10, guest rating 9.3
    Superb - 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: US$127.68
    Scored out of 10, guest rating 9.3
    Superb - 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: US$127.68
    Scored out of 10, guest rating 9.3
    Superb - 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, 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
  • 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
  • Avg. price/night: US$2,342.70
    Scored out of 10, guest rating 9.2
    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
  • 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
  • Avg. price/night: US$111.28
    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