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Vacation Homes in Chianti Region

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Relax by the pool surrounded by lush greenery and well-maintained landscaping.

Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany

9.4 out of 10, Exceptional, (48)
"A fantastic place to visit Tuscany from. The pool is great and the owners are very friendly."
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Farmhouse in the heart of the real chiantishire
Traditional stone building with a charming entrance, surrounded by potted plants and a wooden door.

Farmhouse in the heart of the real chiantishire

10.0 out of 10, Exceptional, (140)
"The house was beautiful and the location was wonderfully quiet and set back from the main road. It’s quaint and cozy. There’s a short gravel road up to the cottage but it’s an easy drive. I would definitely book again."
Farmhouse in the heart of the real chiantishire
A wonderful country house in the heart of Chianti
Relax in a serene garden setting with a table and chair, surrounded by lush greenery and a vase of fresh flowers.

A wonderful country house in the heart of Chianti

9.8 out of 10, Exceptional, (22)
"We enjoyed a relaxing week in this beautiful apartment surrounded by lush gardens with a view of the Tuscan hills. Our host was charming and welcoming. "
A wonderful country house in the heart of Chianti
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Relax in this inviting living room with a comfortable sofa, dining table for two, and a staircase leading to an upper level.

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.

8.8 out of 10, Excellent, (20)
"excellent"
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Residence Le Chiuse -Casa Marrone
Relax by the pool with lounge chairs and umbrellas, surrounded by a scenic view of the hills and a nearby building.

Residence Le Chiuse -Casa Marrone

10.0 out of 10, Exceptional, (15)
"We were 4 adults and a 2 year old child and we had an amazing week here. Anna and Dino are very welcoming and it's easy to feel at home. We would recommend this place to anyone!"
Residence Le Chiuse -Casa Marrone
Villa with large garden in the Chianti hills
Relax in a serene outdoor space with a gazebo, dining table, and comfortable seating.

Villa with large garden in the Chianti hills

9.4 out of 10, Exceptional, (70)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
Villa with large garden in the Chianti hills
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite

10.0 out of 10, Exceptional, (23)
"Lovely place"
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
The Fox - Comfort and luxury. Perfect location for your preciouse holidays
Cozy space with a traditional chair, wooden table, and chandelier, offering a view of lush greenery.

The Fox - Comfort and luxury. Perfect location for your preciouse holidays

10.0 out of 10, Exceptional, (1)
"A une demie heure de Florence, en plein Chianti, dans la nature, ce logement est plein de charme, très propre très agréable au calme, et la propriétaire très accueillante. On y a passé un excellent séjour ! (Petit conseil si vous avez une voiture un peu basse, pour y accéder la route n’est pas goudronnée)."
The Fox - Comfort and luxury. Perfect location for your preciouse holidays
Leo&Kira House
Restful retreat with a neatly made bed, featuring a white mattress and patterned pillows, set against a classic metal headboard.

Leo&Kira House

10.0 out of 10, Exceptional, (1)
"This beautiful old house in Greve is very charming and true to Italian style, made of stones. The downstairs room is a combination of bedroom and living with a TV, with access to the yard. There is bathroom downstairs. Upstairs has two connected rooms with queen size beds un each and one bathroom. Downstairs there's a good size kitchen with a fridge, stove, and a table. My only issue with the place was that there were no screens on the windows so when you opened them sometimes you'd get flies...
Leo&Kira House
Amazing home in Castelfranco Piandiscó
Pool

Amazing home in Castelfranco Piandiscó

Amazing home in Castelfranco Piandiscó
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
Relax by the resort's large pool, surrounded by lounge chairs and a picturesque bridge.

Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.

9.0 out of 10, Wonderful, (11)
"8 of us stayed for 4 nights and it was fantastic! mario, the owner was gracious and expediant with messages. Mamma and Nonna pasta made a meal fit for kings ad queens!! still talking about it. 10 minutes from greve in chianti, 1 minute walk to pizza joinjt. 5 minute drive to duda restaurant, 10 minutes to filigne valdarno and its train station to florence. will be back again and again!"
Casa l'Oca, a spacious and bright house in the heart of Tuscany, in the Chianti area.
Apartment House with garden Tuscany Chianti , Florence 15km.
Guests can enjoy a refreshing swim in the pool surrounded by lush gardens and a scenic mountain view.

Apartment House with garden Tuscany Chianti , Florence 15km.

9.8 out of 10, Exceptional, (72)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Apartment House with garden Tuscany Chianti , Florence 15km.
[Chianti] Riccimballa Luxury Penthouse
Enjoy a serene view of the lush landscape from this outdoor terrace with a table and chairs.

[Chianti] Riccimballa Luxury Penthouse

10.0 out of 10, Exceptional, (1)
"The location is amazing. House is surrounded by hills and valleys. Perfect view of Tuscany. Plenty of amenities. Very spacious and clean house. Stay is on the second floor so be prepared to carry the luggage. There are two bathrooms but only one shower. The shower drain was not properly draining so was a bit of an inconvenience since we were 8. Good for smaller groups. Highly recommend this stay. I was there during the end of March, was a bit chilly but I am sure it will be more beautiful in...
[Chianti] Riccimballa Luxury Penthouse
Farmhouse in Tuscany With Pool and Organic Garden
Traditional architecture meets serene garden surroundings, offering a peaceful dining area with a table and chairs.

Farmhouse in Tuscany With Pool and Organic Garden

7.0 out of 10, Good, (2)
"Beautiful views out in the Tuscan countryside in a vineyard. If you are looking for peace and quiet, this place is wonderful. "
Farmhouse in Tuscany With Pool and Organic Garden
3 bedroom cozy home in Poggibonsi SI
Step into a charming traditional building with a lush, inviting atmosphere and a cozy outdoor seating area.

3 bedroom cozy home in Poggibonsi SI

7.0 out of 10, Good, (2)
"Propriété bien distribuée dans un cadre champêtre très agréable Appartement spacieux avec de nombreuses baies vitrées donnant sur des terrasses. Attention chemin d’accès non goudronné avec de nombreuses ornières."
3 bedroom cozy home in Poggibonsi SI
Capella by Interhome
Relax in the outdoor seating area with wicker furniture and enjoy the view of the surrounding landscape.

Capella by Interhome

9.0 out of 10, Wonderful, (2)
"Apartament dobrze przygotowany, bardzo czysto. Duży plus za możliwość pobytu ze zwierzakami. Ładny widok z tarasu. Kuchnia trochę ciasna. Niestety internet dostępny tylko na tarasie, bardzo słaby."
Capella by Interhome
Relaxing Margherita Home Private Garden, Bucine, Italy
Enjoy al fresco dining and games on the patio, featuring a barbecue grill and ping pong table.

Relaxing Margherita Home Private Garden, Bucine, Italy

10.0 out of 10, Exceptional, (1)
"Our stay was awesome. Thank you very much.Only complaint: there was no toilet paper when we arrived. Although our host hopped on the problem right away, he brought us 2 rolls. Total. 1 for each bathroom. There were 5 of us and we stayed Mon-Thu. Kind of odd…Other than that, it was great. Would do it again."
Relaxing Margherita Home Private Garden, Bucine, Italy
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Relax by the serene pool surrounded by lush greenery and breathtaking views.

Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti

9.8 out of 10, Exceptional, (60)
"We spent 3 weeks in Europe from Barcelona to Cadaques to Provence to Cannes to Nice to Monaco to Rome and Castellina in Chianti. Our stay in Stella at this location was our absolute favorite. Federico was very kind kind, greeted us upon arrival, helped us with questions, and gave us suggestions around the area. We highly recommend this place and are already making our plans to return."
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
Home Elena private garden Chianti view, Greve in Chianti, Italy
Relax in style with a patio featuring a rustic building, lounge chairs, and a shaded table.

Home Elena private garden Chianti view, Greve in Chianti, Italy

Home Elena private garden Chianti view, Greve in Chianti, Italy
Capanna di Sopra by Interhome
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Capanna di Sopra by Interhome

9.8 out of 10, Exceptional, (17)
Capanna di Sopra by Interhome
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."
Anonymous traveler 1-night trip
Posted 3 days ago
Hotel Borgo di Cortefreda Relais