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The best vacation rentals in Castellina in Chianti

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

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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Offering a garden and garden view, Casa Vacanze Squarcialupi is set in Castellina in Chianti, 20 km from Piazza Matteotti and 21 km from Piazza del Campo. This apartment offers free private parking, a 24-hour front desk and free WiFi. Featuring family rooms, this property also provides guests with a terrace.

Spacious, clean, well fitted apartment offering an absolutely picturesque view.

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9.3
Wonderful
288 reviews
Price from
£119
per night

Set in Castellina in Chianti and only 22 km from Piazza Matteotti, Agriturismo La Ferrozzola offers accommodation with pool views, free WiFi and free private parking. The property features garden views and is 24 km from Piazza del Campo and 43 km from Pitti Palace. Featuring family rooms, this property also provides guests with a seasonal outdoor pool.

Spacious bedrooms and locations. Good deal considering we booked last minute. Easy check-in and close to the city.

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9.1
Wonderful
119 reviews
Price from
£117
per night

Located in Castellina In Chianti, Locanda La Casina Di Lilliano offers free Wi-Fi, an outdoor pool and air-conditioned rooms with a flat-screen TV.

Rooms at La Casina Di Lilliano have tiled floors, wood-beamed ceilings and original stone walls. Each includes a private bathroom with shower.

A beautiful place in the middle of the vines. The people were adorable to us. I strongly recommend having dinner there, the food was absolutely delicious !!

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9.2
Wonderful
391 reviews
Price from
£102
per night

Located 5 km from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodation with a patio. WiFi is free throughout, and there is also a terrace.

location, scenery, authenticity, Felt like I belonged there. Felt like home!

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9
Wonderful
254 reviews
Price from
£237
per night

Overlooking the Chianti hills, Agriturismo Casale Dello Sparviero is set in a former monastery. It features a panoramic garden and free Wi-Fi throughout.

With garden views, apartments all come with terracotta floors and a living room with a sofa and a TV. The kitchenette is equipped with a refrigerator.

The swimming pool with a view to the vinyards is top! Also you can have a breakfast outside with a view of the countryside. Complimentary wine on arrival

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9.3
Wonderful
395 reviews
Price from
£120
per night

Set next to the 13th-century Castle of Grignano, this charming stone farmhouse is 7 km outside Castellina in Chianti. Surrounded by nature, it features a large garden with tables and chairs.

La FIABA is set in the Chianti wine district, in an area famous for its Gallo Nero wine. Tours of an organic winery are available on request.

It was a nice & comfy stay in this cute house. It’s a cool and rustic house that Simone has taken care of very well. Room is very clean and cozy. Simone made all pastries for the breakfast for the guests. It’s very nice to have a breakfast in his cute kitchen, sharing traveling information with other guests as well. I highly recommend this place.

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9.2
Wonderful
189 reviews
Price from
£68
per night

Castello La Leccia is a restored mediaeval hamlet, featuring an 11th-century castle, an outdoor swimming pool, and free Wi-Fi. The property is set on a hill, and offers a terrace with views of the Tuscan countryside. Castellina in Chianti is 2 km away.

Staff was outstanding as well as the service. I would highly recommend this hotel. The location and surroundings are beautiful.

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9.7
Exceptional
340 reviews
Price from
£244
per night

Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena.

Guests can rent bikes in the village and ride around the countryside, or just relax in the large garden with sun loungers.

It’s a very comfortable place with amazing hosts. We had a great time and enjoyed the breakfast and dinners served by the hosts during our stay. Also very good suggestions made by them that elevated our experience. Also they have a very good pool and very quite and secluded place.

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9.7
Exceptional
126 reviews
Price from
£296
per night

The Residenzia Del Sogno is in the heart of the Chianti region, surrounded by vineyards and gardens with barbecue facilities. It offers free parking and free Wi-Fi. The outdoor pool offers views of the Tuscan countryside.

Overall our experience was superb. The hosts were exceptional, the rooms were charming and comfortable, and the facilities were great. Breakfast was pretty good, and the hosts clearly put a lot of effort into it.

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9.2
Wonderful
162 reviews
Price from
£126
per night

In the heart of Tuscany’s Chianti region, Relais Riserva di Fizzano has gardens, a gourmet restaurant, and a large pool.

The apartments are air-conditioned and boast tiled floors, wooden ceilings, and fireplaces. Each apartment has a fully equipped kitchen.

Stunning stone villa hotel on the hillside surrounded by vineyards. The pool and chaise lounges were lovely for our family. The breakfasts were outstanding. Ana and Ilaria were so accommodating with booking cooking classes (highly recommend Virna and Claudio's class down the road) and winery picnics.

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9
Wonderful
309 reviews
Price from
£204
per night

Most booked vacation rentals in Castellina in Chianti this month

Enjoy breakfast in Castellina in Chianti!

  • Querceto Di Castellina
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 254 reviews

    Located 3.1 mi from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodations with a patio.

    Location was excellent and staff were very friendly

  • La FIABA
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 189 reviews

    Set next to the 13th-century Castle of Grignano, this charming stone farmhouse is 4.3 mi outside Castellina in Chianti. Surrounded by nature, it features a large garden with tables and chairs.

    Accueil disponibilité confort propreté petit déjeuner

  • Luxor Chianti Glamping village
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 651 reviews

    Luxor Chianti Glamping village in Castellina in Chianti provides accommodations with a seasonal outdoor swimming pool, a garden, and a bar.

    Cool location with amazing facilities, great value

  • AZ.AGR.POGGIO REGINI
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 179 reviews

    Offering quiet street views, AZ.AGR.POGGIO REGINI in Castellina in Chianti offers accommodations, a garden, and barbecue facilities.

    Posizione, genuinità, bontà del cibo e del vino e cortesia dei proprietari

  • Agriturismo Villa Godenano - Pool&Relax
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 619 reviews

    Agriturismo Villa Godenano - Pool&Relax is a recently renovated country house in Castellina in Chianti where guests can make the most of its pool with a view, garden, and bar.

    Very good breakfast. Very nice and friendly staff.

  • Mariani Bed&Breakfast
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 227 reviews

    Mariani Bed&Breakfast is a 5-minute walk from Castellina in Chianti. It offers a garden with terrace. A continental breakfast is provided daily.

    The view. The Location The checkin and out by the owner.

  • Castello di Fonterutoli Wine Resort
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 842 reviews

    Castello di Fonterutoli Wine Resort is a medieval country village in Tuscany's Chianti wine district 3.1 mi outside Castellina in Chianti. It offers a restaurant and wine cellar to visit.

    Rooms, buildings and area around are all beautiful.

  • Podere Palazzolo (ADULTS ONLY)
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 129 reviews

    Podere Palazzolo is a country farmhouse set outside Castellina in Chianti. It has large gardens with swimming pool overlooking the Chianti Valley. Parking and Wi-Fi are free.

    Staff accogliente e attento alle esigenze degli ospiti. Panorama mozzafiato

These vacation rentals in Castellina in Chianti have options with FREE cancellation

  • Casa Vacanze Squarcialupi
    Free cancellation options available
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 288 reviews

    Offering garden views, Casa Vacanze Squarcialupi in Castellina in Chianti provides accommodations, a garden, and a terrace.

    Stunning location with views over the Tuscan hills.

  • Residenzia Del Sogno
    Free cancellation options available
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 162 reviews

    The Residenzia Del Sogno is in the heart of the Chianti region, surrounded by vineyards and gardens with barbecue facilities. It offers free parking and free Wi-Fi.

    Posto, accoglienza, riservatezza e cura particolari

  • Casa Gosi
    Free cancellation options available
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 12 reviews

    Featuring a garden, Casa Gosi provides accommodations in Castellina in Chianti. This property offers access to a balcony, free private parking, and free Wifi.

    maison ancienne bien rénovée avec tout l'équipement

  • Collelungo
    Free cancellation options available
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 238 reviews

    Set in the Tuscan countryside, Collelungo is 2.5 mi from the center of Castellina in Chianti. It offers a free outdoor pool, a sun terrace, and a garden with BBQ facilities.

    location, view, swimming pool, friendly staff, clean

  • Villa Cristina
    Free cancellation options available
    7.8
    Scored 7.8
    Good
    Rated good
     · 400 reviews

    Villa Cristina is a 5-minute walk from Castellina in Chianti town center. It offers an outdoor pool and a garden. A continental breakfast is served buffet style every morning.

    Nice Pool, nice village, nice people. Anytime again

  • Casafrassi
    Free cancellation options available
    7.3
    Scored 7.3
    Good
    Rated good
     · 300 reviews

    Casafrassi is an 18th-century villa with free WiFi located in a panoramic setting less than 5 minutes’ drive from Castellina in Chianti. This large estate features an outdoor pool.

    Beautiful surroundings, friedly and helpful staff.

  • Agriturismo La Ferrozzola
    Free cancellation options available
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 119 reviews

    Agriturismo La Ferrozzola offers accommodations in Castellina in Chianti, 26 miles from Pitti Palace and 27 miles from Strozzi Palace. 14 miles from Piazza Matteotti and 15 miles from Piazza del Campo...

    Большие комнаты. Чудесный вид вокруг дома. Бассейн и т д

  • Locanda La Casina Di Lilliano
    Free cancellation options available
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 392 reviews

    Located in Castellina In Chianti, Locanda La Casina Di Lilliano offers free Wi-Fi, an outdoor pool and air-conditioned rooms with a flat-screen TV.

    Amazing location, pool view to enjoy and really nice room for two!

Highly-rated vacation rentals in Castellina in Chianti

  • Agriturismo Casale Dello Sparviero
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 395 reviews

    Overlooking the Chianti hills, Agriturismo Casale Dello Sparviero is set in a former monastery. It features a panoramic garden and free Wi-Fi throughout.

    Everything, a butifull place in the Tuscan countryside.

  • Castello La Leccia
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 340 reviews

    Castello La Leccia is a restored medieval hamlet, featuring an 11th-century castle, an outdoor swimming pool, and free Wi-Fi.

    The location, the staff, the food and the wine were great!

  • Villa Di Capovento
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 126 reviews

    Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena.

    The evening meal and breakfast was exceptional. Home cooked.

  • Relais Riserva di Fizzano
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 309 reviews

    In the heart of Tuscany’s Chianti region, Relais Riserva di Fizzano has gardens, a gourmet restaurant, and a large pool.

    Beautiful scenery, really helpful staff,good food.

  • CASA IL MANDORLO NEL CHIANTI
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 22 reviews

    CASA IL MANDORLO NEL CHIANTI is located in Castellina in Chianti, just 13 miles from Piazza del Campo and 14 miles from Piazza Matteotti.

    The apartment is quiet and clean. the location is good if you drive car to explore the area.

  • Casa VANINA-self check-in
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 17 reviews

    Featuring a garden, Casa VANINA-self check-in features accommodations in Castellina in Chianti. The vacation home features both Wifi and private parking free of charge.

    Sehr schönes Haus und sehr schöne, abgeschiedene Lage

  • MEA CASA Toscana
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 89 reviews

    MEA CASA Toscana in Castellina in Chianti provides accommodations with an open-air bath, a garden, and barbecue facilities.

    Toppen läge fantastiskt bemötande av värdparet! Vi kommer tillbaka!

  • Cipressini
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 22 reviews

    Providing garden views, Cipressini in Castellina in Chianti provides accommodations and a garden. This property offers a pool with a view, free Wifi, and free private parking.

    Great place, very nice owner, amazing pool, very well equipped beautiful house

FAQ about vacation rentals in Castellina in Chianti







Vacation Rentals That Guests Love in Castellina in Chianti

  • 9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 309 reviews
    We loved the Villa, everything was perfect, the 360 views are to die for. Rooms are very clean, spacious and comfortable. We got to use the pool even it was a bit cold for swimming but kids could not resist. The grounds are gorgeous. Location is perfect, half hour from San Gimignano and Siena, there are plenty of restaurants and small deli within 10 min drive. Breakfast is very nice. We loved our stay !
    Vladlena
    Family with young children
  • Avg. price/night: £161.32
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 619 reviews
    Villa Godenano exceeded all of our expectations! From the moment we arrived, everything was perfect. The staff was absolutely marvelous - welcoming, attentive, and always ready to assist with any request. The breakfast provided each morning was delicious, offering a wide variety of options to suit every taste. We looked forward to starting each day with such a delightful meal. Our room was impeccably clean and beautifully appointed, providing a comfortable and relaxing atmosphere throughout our stay.
    Saranda
    Group
  • Avg. price/night: £84.99
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 227 reviews
    Excellent location to village, exceptional hospitality (Serena helped w/recommendations etc), beautiful view from room, very clean, comfortable bed, good security, included parking, great value.
    Lysa
    Young couple
  • 9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 126 reviews
    The hosts were very friendly and provide a great service to their customers. They cooked for us and were accommodating to any request you may have. The rooms were spacious and clean. The property itself is located on top of a hill overlooking the hills of Tuscany. In warmer weather the use of the pool would be a lot of fun. I would recommend Villa Di Capovento to anyone who is considering stay at an Agriturismo.
    John
    Young couple
  • 9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 254 reviews
    The complex of villas/units is very impressive. The units provide complete privacy. Very kind staff. good breakfast
    ela
    Family with young children
  • 9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 89 reviews
    A dream stay in Tuscany! The host, Elena was very kind, welcoming and helpful. She made us feel like family. The villa and surrounding are stunning, this place is exactly how we pictured our trip before we arrived. The apartment is perfectly set up. I'd love to come back there again during summer time!
    agzim
    Family with young children
  • Avg. price/night: £164.88
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 842 reviews
    Wonderful off the beaten path property with a very special family owned resort that encompasses the whole village. Beautiful new winery with fantastic tours!
    John
    Family with young children
  • 9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 660 reviews
    Beautiful hotel in the beautiful Tuscan village of Castallina In Chianti. Great rooms, fantastic views from the restaturant terrace. Staff were excellent
    Greg
    Young couple
  • Avg. price/night: £164.88
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 842 reviews
    Beautiful historic wine village with a wonderful atmosphere and location.
    Calvin
    Young couple
  • Avg. price/night: £161.32
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 619 reviews
    Location near village, breakfast, staff, pool, view, Bianca cat…
    Sari
    Travelers with friends
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