Search Guest Houses in Chianti Region

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Chianti Region guest houses

Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (182 reviews)
"My fiancé and I took a rental car from Florence to do an overnight stay here and our only regret was that we did not choose to stay longer. This resort was the absolute highlight of our trip. The views are stunning, the wine is superb, and the staff and amenities are high-class. My only advice to not overpack so you can bring home some bottles of wine and olive oil!"
United States
Richard
The price is HK$2,787
HK$3,139 total
includes taxes & fees
11 May - 12 May
Dievole Wine Resort

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (23 reviews)
"Room was very clean and comfortable with gorgeous view of the Tuscan hillside. The owners were very hospitable and accommodating."
United States
Nina
The price is HK$902
HK$1,028 total
includes taxes & fees
6 May - 7 May
Casa di Palaia

Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (32 reviews)
"Beautiful boutique type stay. They are so welcoming and kind. Room was spacious, bed was comfortable. Breakfast was very tasty. Walked around the village and it was beautiful. Not one complaint, book your stay! "
United States
Shannon
The price is HK$982
HK$1,080 total
includes taxes & fees
6 May - 7 May
Dimora Casa Eugenia

Homelink Poggibonsi

Homelink Poggibonsi
Barberino Tavarnelle
5.8 out of 10, (14 reviews)
"There was Ants in the room and property is in very bad condition "
United Kingdom
Avinash
The price is HK$375
HK$449 total
includes taxes & fees
7 May - 8 May
Homelink Poggibonsi

Il Pergolato Apartment – Villa Assolata

Il Pergolato Apartment – Villa Assolata
Pietraviva
The price is HK$5,275
HK$5,311 total
includes taxes & fees
6 May - 7 May
Il Pergolato Apartment – Villa Assolata

Carla's Rooms with Private Bathroom & Shared Kitchen

Carla's Rooms with Private Bathroom & Shared Kitchen
Oltrarno
8.0 out of 10, Very good, (8 reviews)
"The room was very nice, a large space, and was in a very quiet area, with transportation close nearby. Easy walking to more "local" spots (out of the city center). The communication was good, and they were quick to respond! The room was clean- but for one bit- there are some dead mosquito residue on the walls. Other than that, great spot, great location, safe location. I recommend for female solo travelers! "
United States
Caitlin
The price is HK$653
HK$1,241 total
includes taxes & fees
6 May - 7 May
Carla's Rooms with Private Bathroom & Shared Kitchen

Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (137 reviews)
"Great clean hotel not far from central Florence. "
United States
David
The price is HK$1,009
HK$1,240 total
includes taxes & fees
25 May - 26 May
Villa Gelsomino Garden

Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (136 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is HK$630
HK$739 total
includes taxes & fees
21 May - 22 May
Villa Montarioso

Tuscany View, Montalcino

Tuscany View, Montalcino
Montalcino
8.8 out of 10, Excellent, (9 reviews)
"The room and adjecent kitchenette across the hall was lovely for our overnight stay. Location was central and within walking distance to everything. No parking on site, which was not an issue for us to walk with our bags from the car. We were told where to park the vehicle overnight and had no concerns."
Canada
Kyra
The price is HK$961
HK$1,130 total
includes taxes & fees
11 May - 12 May
Tuscany View, Montalcino

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (17 reviews)
"Excellent room and food. Great location!"
United States
Saurabh
The price is HK$2,240
HK$2,513 total
includes taxes & fees
11 May - 12 May
Poggio Paradiso Resort & Spa

Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (34 reviews)
"This was our second time staying here-- so charming and AMAZING breakfast❤️❤️❤️"
United States
Sasha
The price is HK$1,078
HK$1,223 total
includes taxes & fees
6 May - 7 May
Villa Sant Andrea

AmiRooms Affittacamere

AmiRooms Affittacamere
Siena City Centre
10.0 out of 10, Exceptional, (13 reviews)
"Thanks to Amina, very welcoming. "
Canada
daniel
The price is HK$1,384
HK$1,559 total
includes taxes & fees
2 Jun - 3 Jun
AmiRooms Affittacamere

Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (84 reviews)
"Really great."
United States
Yael
The price is HK$1,345
HK$1,516 total
includes taxes & fees
7 May - 8 May
Residenza d'Epoca Le Aquile

L'Antico Borgo di Torri

L'Antico Borgo di Torri
Sovicille
8.0 out of 10, Very good, (1 review)
"Appartamento confortevole, Lorenzo oste disponibile e molto simpatico. Faceva molto caldo e l'aria condizionata sarebbe gradita. Borgo piccolo ma interessante, ottimo ristorante vicinissimo. Ci torneremo!"
Italy
Anonymous traveller
The price is HK$558
HK$760 total
includes taxes & fees
15 May - 16 May
L'Antico Borgo di Torri

B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (117 reviews)
"The room was very clean and staff provided great recommendations for dinner. The room is in a great location very close to the Duomo."
Canada
Chad
The price is HK$874
HK$998 total
includes taxes & fees
5 Jun - 6 Jun
B&B Le Aquile

Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
10.0 out of 10, Exceptional, (34 reviews)
"Lovely clean rooms, modern with lovely historical touches. Proprietor was lovely and accommodating "
Canada
Evelyn
The price is HK$1,281
HK$1,446 total
includes taxes & fees
19 May - 20 May
Residenza d'Epoca San Martino 29

Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (36 reviews)
"We really enjoyed our stay!! Everyone was accomodating and we loved Siena."
United States
Linda
The price is HK$1,411
HK$1,589 total
includes taxes & fees
6 May - 7 May
Blossoms of Siena

Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.2 out of 10, Very good, (99 reviews)
"The room was clean and comfortable. Never met the staff; checkin was remote."
United States
John
The price is HK$496
HK$583 total
includes taxes & fees
7 May - 8 May
Relais La Corte Dei Cavalieri

B&B San Francesco

B&B San Francesco
Cortona Old Town
8.8 out of 10, Excellent, (58 reviews)
"Lovely place, I looking the beautiful San Francesco church. Excellent breakfast!"
United Kingdom
Esther
The price is HK$607
HK$841 total
includes taxes & fees
25 May - 26 May
B&B San Francesco

Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house
San Gimignano City Centre
9.8 out of 10, Exceptional, (7 reviews)
"Excelente ubicación y excelente mantenimiento. La cama de mstrimonio un poco justa, pero ha sido una estancia de 10."
Spain
Gema
The price is HK$850
HK$980 total
includes taxes & fees
13 May - 14 May
Duccio Nacci Rooms - guest house
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
977
Accommodation
8 Guest Houses
Lowest Price
HK$449
Highest Price
HK$5,311

Explore a world of travel with Expedia