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

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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.

S
Silke
From
France
EVERYTHING was perfect (We are hesitating to rate because we would like to keep this B&B as a secret 🤫😜! Very dog friendly. Parking unter olive trees. The BEST staff EVER! The pool... marvellous! Perfectly situated, have fun with your e-Bikes! Olive oil and wine (Chianti classico) tasting. Small but sufficient store near by (foot distance, as well as excellent truffle authentic restaurant.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 147 reviews
Price from
US$241.44
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.

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, 139 reviews
Price from
US$174.96
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.

M
Maree
From
Australia
The staff were amazing and very friendly. They were genuinely wanting to make each visitors experience the best it could be.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 313 reviews
Price from
US$233.84
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, 11 reviews
Price from
US$540.99
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.

P
Paul
From
Spain
Great place for a bigger family or a group of friends with a spectacular view. There are multiple terraces, a barbecue place and a large table inside, which all are all very comfortable to hang around with a bigger group of people. Due to heavy rains we had some issues with the electricity as apparently almost everybody in the area. The host took care of it immediately and the communication was very pleasant.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 19 reviews
Price from
US$4,121.77
1 night, 2 adults

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.

H
Heinersdorff
From
Germany
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!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 78 reviews
Price from
US$2,332.80
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.

в
валентина
From
Russia
Splendid breakfast,good fresh room and great Monica!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 83 reviews
Price from
US$182.89
1 night, 2 adults

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$110.81
1 night, 2 adults

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
Alyssa
From
Australia
Beautiful property, great views and lovely gardens.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 679 reviews
Price from
US$170.22
1 night, 2 adults

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.

D
David
From
United Kingdom
A truly wonderful place to stay. It is a wonderful location amongst the vineyards and so peaceful with incredible views. The staff are exceptional. We also did a tour of the winery which was fabulous. The owner Francesco was warm and friendly and the food was excellent. Their own Chianti Classico is served and we were so impressed we bought 3 cases and shipped them back to the UK. We will certainly go there again.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 358 reviews
Price from
US$220.19
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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These holiday rentals in Gaiole in Chianti and nearby have options with free cancellation

  • Relais Santa Cristina

    Radda in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 420 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$140.83 per night
  • Le Lappe

    Cavriglia
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 207 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$334 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$183.71 per night
  • Agriturismo Malpensata

    Radda in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 271 reviews

    Featuring a garden and views of city, Agriturismo Malpensata is a farm stay situated in a historic building in Radda in Chianti, 19 km from Piazza Matteotti.

    From US$123.64 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$158.63 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, 541 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.

  • 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$183.71 per night
  • Wine Resort Dievole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 591 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 US$751.16 per night

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$110.81 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$295.10 per night
  • L' Antico Comune

    Cavriglia
    8.0+ review score
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 90 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$81.65 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$104.98 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 45 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$173.08 per night
  • Amoliv

    Arezzo
    8.0+ review score
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 14 reviews

    Boasting air-conditioned accommodation with a private pool, pool view and a patio, Amoliv is set in Arezzo. This property offers access to a balcony, table tennis, free private parking and free WiFi.

  • 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$108.13 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 517 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$134.64 per night

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, 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.

  • 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 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$227.45 per night
  • 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.

    From US$540.04 per night

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$257.54
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 679 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$92.15
    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
  • Avg. price/night: US$92.15
    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
  • Avg. price/night: US$92.15
    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
  • 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$2,332.80
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 78 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$110.81
    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