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 RM1,416
RM1,595 total
includes taxes & fees
5 May - 6 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 RM476
RM542 total
includes taxes & fees
4 May - 5 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 RM543
RM597 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 RM190
RM228 total
includes taxes & fees
6 May - 7 May
Homelink Poggibonsi

Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (136 reviews)
"Great clean hotel not far from central Florence. "
United States
David
The price is RM513
RM630 total
includes taxes & fees
17 May - 18 May
Villa Gelsomino Garden

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 RM356
RM657 total
includes taxes & fees
6 May - 7 May
Carla's Rooms with Private Bathroom & Shared Kitchen

Florence David's Guesthouse

Florence David's Guesthouse
Historic Centre of Florence
9.0 out of 10, Wonderful, (2 reviews)
"The room was very small and needs some"
United States
Egla
The price is RM619
RM737 total
includes taxes & fees
12 May - 13 May
Florence David's Guesthouse

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 RM487
RM573 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 RM1,139
RM1,277 total
includes taxes & fees
11 May - 12 May
Poggio Paradiso Resort & Spa

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 RM343
RM401 total
includes taxes & fees
10 May - 11 May
Villa Montarioso

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 RM546
RM620 total
includes taxes & fees
4 May - 5 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 RM703
RM792 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 RM720
RM810 total
includes taxes & fees
4 May - 5 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 RM329
RM436 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 RM480
RM546 total
includes taxes & fees
25 May - 26 May
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 RM651
RM735 total
includes taxes & fees
5 May - 6 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 RM717
RM807 total
includes taxes & fees
4 May - 5 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 RM377
RM433 total
includes taxes & fees
10 May - 11 May
Relais La Corte Dei Cavalieri

Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (176 reviews)
"I would highly recommend this property. The staff were very amazing."
United States
Cynthia
The price is RM402
RM465 total
includes taxes & fees
17 May - 18 May
Residenza d'Epoca Palazzo Buonaccorsi
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
1,096
Accommodation
8 Guest Houses
Lowest Price
RM228
Highest Price
RM1,595

Explore a world of travel with Expedia