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
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Chianti Region guest houses

Chapel

1. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (207 reviews)
"Canadian hospitality can learn from this INCREDIBLE winery❣️ HIGHLY recommended"
Canada
Nicole
The price is P20,099
P22,685 total
includes taxes & fees
Aug 25 - Aug 26
Dievole Wine Resort
Exterior

2. Casa di Palaia

Casa di Palaia
Greve in Chianti
9.2 out of 10, Wonderful, (27 reviews)
"The bedroom was large, clean and comfortable as was the bathroom. In particular the owners were very friendly and helpful."
United Kingdom
Steven
The price is P8,252
P9,365 total
includes taxes & fees
Aug 23 - Aug 24
Casa di Palaia
Garden

3. 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 P3,448
P4,081 total
includes taxes & fees
Sep 20 - Sep 21
Homelink Poggibonsi
27-inch flat-screen TV with digital channels, TV, heated floors

4. 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 P8,399
P9,239 total
includes taxes & fees
Aug 22 - Aug 23
Dimora Casa Eugenia
Restaurant

5. Borgo Nuovo San Martino

Borgo Nuovo San Martino
Bucine
6.8 out of 10, (10 reviews)
"Definitely going back in the summer"
United States
Josimar
The price is P6,778
P7,744 total
includes taxes & fees
Sep 21 - Sep 22
Borgo Nuovo San Martino
View from property

6. Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (140 reviews)
"Great place nice location"
United States
Zaid
The price is P3,487
P4,859 total
includes taxes & fees
Aug 22 - Aug 23
Villa Gelsomino Garden
Reception

7. Foresteria Valdese di Firenze - Casa per Ferie

Foresteria Valdese di Firenze - Casa per Ferie
Historic Centre of Florence
8.8 out of 10, Excellent, (235 reviews)
"I had a lovely stay! Staff were helpful"
United States
Alloura
The price is P5,114
P6,490 total
includes taxes & fees
Aug 31 - Sep 1
Foresteria Valdese di Firenze - Casa per Ferie
Courtyard

8. Drom Florence Rooms & Apartments

Drom Florence Rooms & Apartments
Historic Centre of Florence
9.8 out of 10, Exceptional, (152 reviews)
"We had a very nice stay. Claudia was very friendly and service minded The place serves continental breakfast - and is a good idea to supplement it a little bit! Nice and quiet area, where you can walk to most things We can only recommend it Else Marie Hansen May 2026"
Denmark
Else Marie
The price is P7,404
P9,008 total
includes taxes & fees
Aug 22 - Aug 23
Drom Florence Rooms & Apartments
Premium bedding, in-room safe, soundproofing, WiFi (free)

9. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (389 reviews)
"Great staff and location"
United States
Albert
The price is P7,427
P9,178 total
includes taxes & fees
Aug 23 - Aug 24
Toscanelli Residenza D'epoca
Garden

10. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (140 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is P5,649
P6,574 total
includes taxes & fees
Sep 8 - Sep 9
Villa Montarioso
Front of property

11. Soprarno Suites

Soprarno Suites
Historic Centre of Florence
9.8 out of 10, Exceptional, (417 reviews)
"The room was lovely and clean, the breakfast was exemplary and the staff were a delight."
United States
Valerie
The price is P17,925
P20,726 total
includes taxes & fees
Aug 24 - Aug 25
Soprarno Suites
Interior

12. Casa Santo Nome di Gesù

Casa Santo Nome di Gesù
Historic Centre of Florence
8.8 out of 10, Excellent, (379 reviews)
"Excellent location and wonderful staff in a unique building with an amazing history."
United Kingdom
Matthew
The price is P7,713
P9,349 total
includes taxes & fees
Aug 27 - Aug 28
Casa Santo Nome di Gesù
Minibar (free items), in-room safe, iron/ironing board, WiFi (free)

13. Residenza D'epoca Poliziano

Residenza D'epoca Poliziano
San Lorenzo
8.8 out of 10, Excellent, (60 reviews)
"Great location and excellent room."
United States
HALE
The price is P5,541
P6,960 total
includes taxes & fees
Aug 23 - Aug 24
Residenza D'epoca Poliziano
Fireplace

14. Ottantotto Firenze

Ottantotto Firenze
Historic Centre of Florence
9.6 out of 10, Exceptional, (176 reviews)
"Quaint boutique hotel in great location. Clean comfortable room and nice breakfast. Wonderful restaurant almost next door and close to train station. Highly recommend."
United States
Timothy
The price is P14,048
P16,461 total
includes taxes & fees
Sep 6 - Sep 7
Ottantotto Firenze
In-room dining

15. Piazza Pitti Palace

Piazza Pitti Palace
Historic Centre of Florence
9.2 out of 10, Wonderful, (140 reviews)
"Great rooms for families. Close to everything! Easy to drive to/"
United States
Raine
The price is P11,809
P14,001 total
includes taxes & fees
Aug 25 - Aug 26
Piazza Pitti Palace
Private kitchen

16. Florence David's Guesthouse

Florence David's Guesthouse
Historic Centre of Florence
9.4 out of 10, Exceptional, (11 reviews)
"This place is exactly what is depicted and the host was extremely responsive and helpful. Would highly recommend!"
Canada
Lauren
The price is P4,679
P6,011 total
includes taxes & fees
Aug 23 - Aug 24
Florence David's Guesthouse
Hypo-allergenic bedding available, minibar, in-room safe, WiFi (free)

17. Palazzo Oliveto

Palazzo Oliveto
Oltrarno
7.6 out of 10, Good, (106 reviews)
"I really enjoyed my stay here. The host was also extremely kind and helpful."
Belgium
Mary Mariam
The price is P4,497
P5,811 total
includes taxes & fees
Aug 22 - Aug 23
Palazzo Oliveto
Desk, laptop workspace, cribs (surcharge), WiFi (free)

18. Maggio Living

Maggio Living
Historic Centre of Florence
10.0 out of 10, Exceptional, (4 reviews)
"Excellent! Perfect location!"
Sweden
Ida
The price is P14,270
P16,561 total
includes taxes & fees
Aug 25 - Aug 26
Maggio Living
1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

19. Fornace Suite

Fornace Suite
Oltrarno
9.8 out of 10, Exceptional, (33 reviews)
"One of the nicest places I've stayed at!"
United Kingdom
Oopdeshwarnathsingh
The price is P10,972
P12,934 total
includes taxes & fees
Aug 27 - Aug 28
Fornace Suite
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

8/10 Good
"We had mixed feelings about our stay. The property and vineyard are beautiful, with fantastic Tuscan views. Our villa was spacious and private, the AC worked extremely well, and the semi-private pool was great with a small child. We booked through Expedia expecting more of a hotel/resort experience, but the villas operate as self-catering rentals. There was no daily housekeeping, fresh towels/linens, or replenishment of basics. We received three coffee pods and were directed to nearby grocery stores for additional provisions, so plan to stock up after arrival. We were surprised that villa guests could not use the main castle pool and were largely separate from the hotel areas. The four villas are in their own chain-link-fenced compound, which felt secluded from the otherwise beautiful property. Cleanliness could have been better: we found quite a bit of hair on arrival, and the shower flooded the bathroom with each use. We chose not to raise this during our stay. The pool itself is gorgeous, but the surrounding area felt unfinished, with loungers on gravel or long grass/weeds, few tables, and limited shade when multiple families were there. Overall, the villa has a lot going for it. Just arrive expecting a self-catering villa rather than the services and amenities of the hotel."
Justin 4-night trip
Posted 4 hours ago
Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,613
Accommodation
8 Guest Houses
Lowest Price
P4,081
Highest Price
P22,685

Explore a world of travel with Expedia