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

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

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, (210 reviews)
"The property is gorgeous with breath taking views everywhere. Staff went above and beyond providing excellent service!! Beautiful Infiniti pool, great food!!"
United States
Karamjit
The price is CA $494
CA $556 total
includes taxes & fees
Oct 11 - Oct 12
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, (29 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 CA $123
CA $142 total
includes taxes & fees
Oct 11 - Oct 12
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 $180
CA $198 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $58
CA $70 total
includes taxes & fees
Sep 27 - Sep 28
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
6.8 out of 10, (10 reviews)
"Definitely going back in the summer"
United States
Josimar
The price is CA $151
CA $173 total
includes taxes & fees
Sep 21 - Sep 22
Borgo Nuovo San Martino
A building with a symmetrical facade, arched windows, and a central door.

6. Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (141 reviews)
"Great place nice location"
United States
Zaid
The price is CA $148
CA $186 total
includes taxes & fees
Sep 17 - Sep 18
Villa Gelsomino Garden
A covered courtyard with columns, a bench, and potted plants.

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, (241 reviews)
"Rooms with AC, shops and laundromats within a block, incredible good restaurants at less than 10 minutes walk"
Canada
Jorge
The price is CA $160
CA $195 total
includes taxes & fees
Oct 12 - Oct 13
Foresteria Valdese di Firenze - Casa per Ferie
A narrow cobblestone street with a parked white scooter and a table with chairs in the background.

8. Drom Florence Rooms & Apartments

Drom Florence Rooms & Apartments
Historic Centre of Florence
9.8 out of 10, Exceptional, (153 reviews)
"Claudia was very helpful and kind! The hotel is a bit out of the way but a nice stay overall. Very clean and exactly what the photos look like."
Canada
Brianna
The price is CA $302
CA $352 total
includes taxes & fees
Sep 27 - Sep 28
Drom Florence Rooms & Apartments
A pathway lined with trees and a large pot in the center.

9. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (141 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is CA $113
CA $132 total
includes taxes & fees
Oct 13 - Oct 14
Villa Montarioso
A dining area with a round table, wooden chairs, and hanging light fixtures.

10. 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 $199
CA $226 total
includes taxes & fees
Sep 27 - Sep 28
podere la strega
A modern bedroom with a minimalist design, featuring a bed with a wooden frame and a large abstract painting on the wall.

11. Fornace Suite

Fornace Suite
Oltrarno
9.8 out of 10, Exceptional, (34 reviews)
"Traveling with my best friends for our friendship anniversary, the accommodations at Fornance Suite were amazing. I’ve recommended this stay to family and friends; if you’re considering staying here, please do! The staff went above and beyond for us during our stay. Our suite was beautiful and extremely clean."
United States
Jordan
The price is CA $435
CA $497 total
includes taxes & fees
Oct 12 - Oct 13
Fornace Suite
A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

12. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (391 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 $248
CA $296 total
includes taxes & fees
Oct 9 - Oct 10
Toscanelli Residenza D'epoca
A hotel room with a bed, two chairs, a window with a view, and a vase with flowers.

13. 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 CA $105
CA $135 total
includes taxes & fees
Sep 13 - Sep 14
Palazzo Oliveto
A cozy reading nook with a fireplace, bookshelves, and comfortable seating.

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 CA $272
CA $322 total
includes taxes & fees
Sep 25 - Sep 26
Ottantotto Firenze
A multi-story building with a classic architectural style, featuring a central entrance with a canopy, and a series of windows on each floor.

15. Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (94 reviews)
"Fantastic location, helpful and welcoming staff, great sized rooms. 10 out of 10, would recommend."
United States
Stephanie
The price is CA $264
CA $297 total
includes taxes & fees
Sep 29 - Sep 30
Residenza d'Epoca Le Aquile
A dining table with breakfast items, a vase with flowers, and a balcony view.

16. 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 CA $472
CA $542 total
includes taxes & fees
Oct 5 - Oct 6
Piazza Pitti Palace
An outdoor courtyard with stone walls, arched doorways, and potted plants.

17. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (195 reviews)
"Thank you so much for a wonderful stay :)"
United Kingdom
Soni
The price is CA $124
CA $144 total
includes taxes & fees
Oct 12 - Oct 13
Residenza d'Epoca Palazzo Buonaccorsi
A grand hallway with a high ceiling, large wooden doors, and classical columns.

18. Casa Santo Nome di Gesù

Casa Santo Nome di Gesù
Historic Centre of Florence
8.8 out of 10, Excellent, (382 reviews)
"Beautiful hotel in great location. Staff really helpful with local knowledge. Communal fridge available at reception, which was great for storing drinks."
United Kingdom
Rebecca
The price is CA $238
CA $281 total
includes taxes & fees
Sep 27 - Sep 28
Casa Santo Nome di Gesù
A hotel room with a bed, a desk, a chair, a television, and an air conditioning unit.

19. Le Nove Muse Guesthouse

Le Nove Muse Guesthouse
San Lorenzo
9.6 out of 10, Exceptional, (11 reviews)
"Excellent to visit Florence"
Canada
Carolyne
The price is CA $155
CA $190 total
includes taxes & fees
Sep 13 - Sep 14
Le Nove Muse Guesthouse
A modern bathroom with a glass shower enclosure, a vanity with a mirror, and a radiator near the window.

20. Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (53 reviews)
"Enjoyed our stay."
United States
Rene
The price is CA $201
CA $228 total
includes taxes & fees
Sep 27 - Sep 28
Residenza d'Epoca San Martino 29
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.
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Top Chianti Region Hotel Reviews

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"Incredible magical place. Couldn’t recommend it more…"
Megan 2-night trip
Posted 3 hours ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
2,278
Accommodation
8 Guest Houses
Lowest Price
CA $70
Highest Price
CA $556

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