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

Search Guest Houses in Chianti Region from CA $68

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

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 CA $349
CA $397 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $139
CA $160 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $167
CA $184 total
includes taxes & fees
Oct 12 - Oct 13
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
5.8 out of 10, (16 reviews)
"There was Ants in the room and property is in very bad condition "
United Kingdom
Avinash
The price is CA $56
CA $68 total
includes taxes & fees
Oct 11 - Oct 12
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 CA $144
CA $165 total
includes taxes & fees
Oct 12 - Oct 13
Borgo Nuovo San Martino
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.

6. Palazzina Fusi

Palazzina Fusi
Historic Centre of Florence
9.2 out of 10, Wonderful, (183 reviews)
"Perfect location! Attentive staff and a very quiet room ."
United States
debbie
The price is CA $136
CA $169 total
includes taxes & fees
Nov 8 - Nov 9
Palazzina Fusi
A living room with a sofa, a coffee table, and a television mounted on the wall.

7. 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 CA $164
CA $199 total
includes taxes & fees
Oct 19 - Oct 20
Residenze Strozzi Firenze
Exterior

8. 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 CA $108
CA $125 total
includes taxes & fees
Nov 4 - Nov 5
AmiRooms Affittacamere
A pathway lined with trees and a large pot in the center.

9. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (144 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is CA $108
CA $127 total
includes taxes & fees
Nov 4 - Nov 5
Villa Montarioso
An outdoor courtyard with stone walls, arched doorways, and potted plants.

10. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (199 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is CA $122
CA $142 total
includes taxes & fees
Nov 2 - Nov 3
Residenza d'Epoca Palazzo Buonaccorsi
A dining area with a round table, wooden chairs, and hanging light fixtures.

11. 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 CA $245
CA $276 total
includes taxes & fees
Oct 14 - Oct 15
podere la strega
A modern hotel room with a bed, two sofas, a table with a candle, glasses, and a champagne bottle.

12. Antico Centro Suites

Antico Centro Suites
Historic Centre of Florence
9.0 out of 10, Wonderful, (368 reviews)
"Clean room, nice staff and excellent location !"
United States
Juliet
The price is CA $147
CA $181 total
includes taxes & fees
Nov 10 - Nov 11
Antico Centro Suites
A modern bathroom with a glass shower enclosure, a vanity with a mirror, and a radiator near the window.

13. 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 CA $167
CA $190 total
includes taxes & fees
Nov 10 - Nov 11
Residenza d'Epoca San Martino 29
A building with a symmetrical facade, arched windows, and a central door.

14. Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
8.8 out of 10, Excellent, (147 reviews)
"Great place nice location"
United States
Zaid
The price is CA $56
CA $84 total
includes taxes & fees
Nov 2 - Nov 3
Villa Gelsomino Garden
A courtyard with a domed building and a bell tower.

15. The Artists' Palace Florence

The Artists' Palace Florence
Historic Centre of Florence
9.4 out of 10, Exceptional, (506 reviews)
"Location, staff, everything is amazing"
Canada
Maryam
The price is CA $145
CA $227 total
includes taxes & fees
Nov 5 - Nov 6
The Artists' Palace Florence
A balcony with wicker furniture, a table with fruit, and a cityscape view.

16. 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 CA $206
CA $233 total
includes taxes & fees
Nov 9 - Nov 10
Blossoms of Siena
A street view with a wooden door, a shop with a sign, and a red car parked on the sidewalk.

17. La Loggia del Porcellino

La Loggia del Porcellino
Historic Centre of Florence
8.6 out of 10, Excellent, (51 reviews)
"Good for solo travel"
Canada
Margarita
The price is CA $123
CA $154 total
includes taxes & fees
Nov 9 - Nov 10
La Loggia del Porcellino
A historic building with intricate architectural details and a dome.

18. Guest House Bel Duomo

Guest House Bel Duomo
Historic Centre of Florence
8.6 out of 10, Excellent, (1,000 reviews)
"Great location and friendly staff! Would stay again."
United States
Tracy
The price is CA $88
CA $116 total
includes taxes & fees
Nov 10 - Nov 11
Guest House Bel Duomo
A narrow street with buildings on either side, a balcony with a table and chairs, and a plant.

19. Le stanze degli amidei

Le stanze degli amidei
Historic Centre of Florence
9.4 out of 10, Exceptional, (143 reviews)
"Perfect location!"
United States
Brian
The price is CA $180
CA $217 total
includes taxes & fees
Nov 3 - Nov 4
Le stanze degli amidei
A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

20. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (394 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 CA $121
CA $156 total
includes taxes & fees
Nov 6 - Nov 7
Toscanelli Residenza D'epoca
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

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

10/10 Excellent
"Great spot and friendly staff."
Chris 4-night trip
Posted 7 hours ago
Villa I Barronci Resort & Spa

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
2,550
Accommodation
8 Guest Houses
Lowest Price
CA $68
Highest Price
CA $397

Explore a world of travel with Expedia