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

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 €315
includes taxes & fees
25 Aug - 26 Aug
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 €130
includes taxes & fees
24 Aug - 25 Aug
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 €49
includes taxes & fees
24 Aug - 25 Aug
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 €128
includes taxes & fees
26 Aug - 27 Aug
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 €108
includes taxes & fees
21 Sept - 22 Sept
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 €71
includes taxes & fees
29 Aug - 30 Aug
Villa Gelsomino Garden
Garden

7. 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 €91
includes taxes & fees
8 Sept - 9 Sept
Villa Montarioso
Standard Double Room, City View (Tornabuoni Small Size Room)

8. 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 €127
includes taxes & fees
25 Aug - 26 Aug
Toscanelli Residenza D'epoca
3-inch Smart TV with digital channels

9. 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 €142
includes taxes & fees
2 Sept - 3 Sept
podere la strega
Fireplace

10. 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 €208
includes taxes & fees
30 Aug - 31 Aug
Ottantotto Firenze
Exterior

11. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (94 reviews)
"Ada the hostess was very kind and helpfull with all our queries Room was spacious bedding excellent Climate control very good we needed it as it was getting very hot in Siena Grazie Mille Ada & Massimo"
Mexico
Carlos
The price is €198
includes taxes & fees
10 Sept - 11 Sept
Residenza d'Epoca Le Aquile
Front of property

12. 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 €288
includes taxes & fees
24 Aug - 25 Aug
Soprarno Suites
Reception

13. 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 €90
includes taxes & fees
31 Aug - 1 Sept
Foresteria Valdese di Firenze - Casa per Ferie
Exterior

14. Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.2 out of 10, Very good, (116 reviews)
"Easy checkin/checkout, easy with the dog also. Very nice scenery, well located, close to the train station, within the walled city. No AC but the there was a decent fan so no sweating at night despite 30C+ weather."
Canada
Ranmal
The price is €68
includes taxes & fees
25 Aug - 26 Aug
Relais La Corte Dei Cavalieri
Apartment, 1 Bedroom, Private Bathroom

15. 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 €81
includes taxes & fees
24 Aug - 25 Aug
Residenza D'epoca Poliziano
Premium bedding, in-room safe, desk, laptop workspace

16. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (51 reviews)
"Enjoyed our stay."
United States
Rene
The price is €130
includes taxes & fees
27 Aug - 28 Aug
Residenza d'Epoca San Martino 29
Terrace/patio

17. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (192 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is €104
includes taxes & fees
24 Aug - 25 Aug
Residenza d'Epoca Palazzo Buonaccorsi
Front of property

18. B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.6 out of 10, Exceptional, (128 reviews)
"Centre of everything and very helpful host"
Canada
kevin
The price is €117
includes taxes & fees
24 Aug - 25 Aug
B&B Le Aquile
Deluxe Studio Suite, City View

19. Maggio Living

Maggio Living
Historic Centre of Florence
10.0 out of 10, Exceptional, (4 reviews)
"Excellent! Perfect location!"
Sweden
Ida
The price is €230
includes taxes & fees
24 Aug - 25 Aug
Maggio Living
Family Apartment | Private kitchen

20. 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 €84
includes taxes & fees
25 Aug - 26 Aug
Florence David's Guesthouse
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 Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."
Natasha 4-night trip
Posted 12 hours ago
Villa Casagrande Resort & SPA

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,363
Accommodation
8 Guest Houses
Lowest Price
€49
Highest Price
€315

Explore a world of travel with Expedia