A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Chianti Region guest houses

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

1. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (214 reviews)
"Our recent stay at the Dievole Wine Resort was incredible! The hospitality is second to none. This is the perfect place to unwind in Tuscany. I wish we could’ve stayed longer! Ciao!"
Canada
Marissa
The price is HK$2,306
HK$2,607 total
includes taxes & fees
28 Oct - 29 Oct
Dievole Wine Resort
An outdoor seating area with tables and chairs, a wooden bar, and a view of the countryside.

2. Casa di Palaia

Casa di Palaia
Greve in Chianti
9.4 out of 10, Exceptional, (31 reviews)
"This is a great place to stay if you want a relaxed feel at home experience when visiting Chianti. The owner will set you up with a good breakfast with various options like boiled eggs, bread, your selection of coffee or cappuccino and varied pastries and fruits. The view and whole scenery is awesome! We hope to be back soon!"
United States
Belisario
The price is HK$792
HK$907 total
includes taxes & fees
8 Oct - 9 Oct
Casa di Palaia
A luxurious room with a chandelier, classical columns, and a dining area with wooden chairs and a table.

3. Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (33 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$1,030
HK$1,133 total
includes taxes & fees
8 Oct - 9 Oct
Dimora Casa Eugenia
A two-story building with a patio area featuring outdoor seating and potted plants.

4. Homelink Poggibonsi

Homelink Poggibonsi
Barberino Val d'Elsa
6.0 out of 10, (15 reviews)
"There was Ants in the room and property is in very bad condition "
United Kingdom
Avinash
The price is HK$325
HK$393 total
includes taxes & fees
11 Oct - 12 Oct
Homelink Poggibonsi
A stone-walled room with a fireplace, a table with chairs, and a hanging light fixture.

5. Borgo Nuovo San Martino

Borgo Nuovo San Martino
Bucine
7.2 out of 10, Good, (11 reviews)
"Definitely going back in the summer"
United States
Josimar
The price is HK$798
HK$913 total
includes taxes & fees
12 Oct - 13 Oct
Borgo Nuovo San Martino
A living room with a sofa, a coffee table, and a television mounted on the wall.

6. Residenze Strozzi Firenze

Residenze Strozzi Firenze
Historic Centre of Florence
8.4 out of 10, Very good, (5 reviews)
"Lovely property.. best location. Everything is 10/10 for me."
Australia
Marie Jo
The price is HK$980
HK$1,183 total
includes taxes & fees
20 Oct - 21 Oct
Residenze Strozzi Firenze
Exterior

7. AmiRooms Affittacamere

AmiRooms Affittacamere
Siena City Centre
10.0 out of 10, Exceptional, (25 reviews)
"We received great instructions from Amina on how to access the room which were easy to follow. If arriving in the day, the ground floor is where a lovely flower shop is, then up a lift. There are then 9 easy steps down to where the room is located. This was our 4th stop on our trip and by far the best room. Although in the centre of everything, the room is super quiet, modern, with a lovely-sized bathroom & powerful shower and great WiFi. We would highly recommend and will definitely return...
United Kingdom
Michelle
The price is HK$663
HK$764 total
includes taxes & fees
4 Nov - 5 Nov
AmiRooms Affittacamere
A hotel room with a large bed, a desk with a chair, a dining area with chairs, and a view of a building through open windows.

8. Palazzina Fusi

Palazzina Fusi
Historic Centre of Florence
9.2 out of 10, Wonderful, (180 reviews)
"Perfect location! Attentive staff and a very quiet room ."
United States
debbie
The price is HK$825
HK$1,013 total
includes taxes & fees
5 Nov - 6 Nov
Palazzina Fusi
A pathway lined with trees and a large pot in the center.

9. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (143 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is HK$643
HK$752 total
includes taxes & fees
3 Nov - 4 Nov
Villa Montarioso
A multi-story building with a classic architectural style, featuring a ground-floor entrance with a canopy and a visible storefront.

10. B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (132 reviews)
"Everything is excellent, if I will come back I will definitely stay again, room is clean and huge for 2 and is near to the Cathedral and Plaza. Ada is an amazing person to talk to."
Canada
Lope
The price is HK$846
HK$966 total
includes taxes & fees
5 Nov - 6 Nov
B&B Le Aquile
A modern bathroom with a glass shower enclosure, a vanity with a mirror, and a radiator near the window.

11. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (60 reviews)
"Such a beautiful place to stay and so handy to the main square and restraunts we loved our stay here"
United Kingdom
Cara
The price is HK$925
HK$1,052 total
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca San Martino 29
A balcony with wicker furniture, a table with fruit, and a cityscape view.

12. Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (45 reviews)
"The convenience of the hotel being so close to so many activities and a lot of restaurants within walking distance from the hotel."
United States
Walter
The price is HK$1,313
HK$1,479 total
includes taxes & fees
7 Nov - 8 Nov
Blossoms of Siena
A dining area with a round table, wooden chairs, and hanging light fixtures.

13. podere la strega

podere la strega
Siena
10.0 out of 10, Exceptional, (4 reviews)
"Vår vistelse på Podere La Strega var fantastisk! Paret som hade hand om oss var alldeles underbara. Frukosten var trevlig vid ett stort gemensamt bord och god mat, mannen på hotellet ordnade en riktigt bra kaffe! Poolområdet var rent och fräsch och det märktes att de tar väl hand om stället. Vi vill åka tillbaka redan nu!"
Sweden
Jenny
The price is HK$1,446
HK$1,626 total
includes taxes & fees
14 Oct - 15 Oct
podere la strega
A historic building with intricate architectural details and a dome.

14. Guest House Bel Duomo

Guest House Bel Duomo
Historic Centre of Florence
8.6 out of 10, Excellent, (1,003 reviews)
"Great location and friendly staff! Would stay again."
United States
Tracy
The price is HK$665
HK$838 total
includes taxes & fees
1 Nov - 2 Nov
Guest House Bel Duomo
A balcony with a view of a pool and landscape, a wooden table with chairs, and a large umbrella.

15. Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (36 reviews)
"This was our second time staying here-- so charming and AMAZING breakfast❤️❤️❤️"
United States
Sasha
The price is HK$968
HK$1,100 total
includes taxes & fees
2 Nov - 3 Nov
Villa Sant Andrea
A storefront with a sign reading 'STUDIO GELATO' and a scooter parked outside.

16. The Florence Crown LR Collection

The Florence Crown LR Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (8 reviews)
"The room was clean and had plenty of space. Every day, the staff cleaned the room and the bathroom. I love the bid mirror. Two days before your arrival, the staff will give you all the information on how to access your room via WhatsApp, including how to access the Wi-Fi. What I loved was that there was an iron for my clothes. One more thing: the location is very close to a supermarket and restaurants, and even a hair salon. The staff is always available through WhatsApp."
United States
Vivian
The price is HK$933
HK$1,132 total
includes taxes & fees
1 Nov - 2 Nov
The Florence Crown LR Collection
A multi-story building with a classic architectural style, featuring a central entrance with a canopy, and a series of windows on each floor.

17. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (95 reviews)
"Ada was wonderful from the first moment we spoke with her until we had to da6 goodbye when we checked. The restaurant she recommended and made reservations for us eas outstanding. She was spot on guiding us to tours around the area. She even helped us with our luggage the first day. Highly recommend!!!"
United States
Scott
The price is HK$1,496
HK$1,681 total
includes taxes & fees
5 Nov - 6 Nov
Residenza d'Epoca Le Aquile
A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

18. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (393 reviews)
"This was the perfect place to stay for my trip to Florence. The location was great, right across from Boboli Gardens, down the street from Ponte Vecchio, and close by a bunch of nice restaurants and wine bars. AC works great too!"
United States
Emily
The price is HK$737
HK$935 total
includes taxes & fees
6 Nov - 7 Nov
Toscanelli Residenza D'epoca
An outdoor courtyard with stone walls, arched doorways, and potted plants.

19. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (198 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is HK$692
HK$805 total
includes taxes & fees
11 Oct - 12 Oct
Residenza d'Epoca Palazzo Buonaccorsi
A covered outdoor dining area with a table and chairs, a pergola with vines, and a tree in the foreground.

20. In Corte - Rooms in Florence

In Corte - Rooms in Florence
Santa Croce
8.4 out of 10, Very good, (6 reviews)
"Property was in a good location. It was very clean. Will definitely stay there again. Make sure you read check in instructions before you arrive to save you some time."
United States
Jennifer
The price is HK$752
HK$933 total
includes taxes & fees
5 Nov - 6 Nov
In Corte - Rooms in Florence
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"What a gorgeous place! We loved it here and can’t wait to go back!"
Sarah 3-night trip
Posted 2 days ago
Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,771
Accommodation
8 Guest Houses
Lowest Price
HK$393
Highest Price
HK$2,607

Explore a world of travel with Expedia