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
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Chianti Region guest houses

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

1. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (218 reviews)
"This stay was absolutely perfect. The staff is amazing and we had a great time! The food is also great!"
Norway
Magdalena
The price is CA $347
CA $394 total
includes taxes & fees
Nov 21 - Nov 22
Dievole Wine Resort
A white planter with colorful flowers on a stone ledge, overlooking a lake and green hills.

2. Casa di Palaia

Casa di Palaia
Greve in Chianti
9.2 out of 10, Wonderful, (33 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 $141
CA $161 total
includes taxes & fees
Oct 28 - Oct 29
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)
"Nice hotel, beautiful large room. Nice view over the river. "
Norway
Hilde Stendal
The price is CA $166
CA $183 total
includes taxes & fees
Oct 30 - Oct 31
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 $53
CA $65 total
includes taxes & fees
Nov 4 - Nov 5
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 $147
CA $168 total
includes taxes & fees
Oct 28 - Oct 29
Borgo Nuovo San Martino
A room with a large window, a potted plant, and a view of a building with an archway.

6. Residenze Strozzi Firenze

Residenze Strozzi Firenze
Historic Centre of Florence
9.0 out of 10, Wonderful, (10 reviews)
"As a solo traveler, this was perfect and so cozy. In the middle of everything and I could easily come back to rest as many times as I needed without it feeling like a hassle. The staff was really helpful too!"
United States
Ariana
The price is CA $144
CA $178 total
includes taxes & fees
Oct 29 - Oct 30
Residenze Strozzi Firenze
A pathway lined with trees and a large pot in the center.

7. 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 $106
CA $124 total
includes taxes & fees
Nov 15 - Nov 16
Villa Montarioso
A room with a large window overlooking a crowded square with historic buildings.

8. Palazzina Fusi

Palazzina Fusi
Historic Centre of Florence
9.2 out of 10, Wonderful, (189 reviews)
"Perfect location! Attentive staff and a very quiet room ."
United States
debbie
The price is CA $119
CA $149 total
includes taxes & fees
Nov 8 - Nov 9
Palazzina Fusi
A narrow courtyard with terracotta steps leading to a door, surrounded by potted plants and a small table with a chair.

9. Corte dell'albero

Corte dell'albero
Historic Centre of Florence
9.4 out of 10, Exceptional, (122 reviews)
"Close location to main train station , about 6 minutes walk , also great location and walkable to most attractions, breakfast was very simple"
United States
Marjan
The price is CA $88
CA $116 total
includes taxes & fees
Nov 1 - Nov 2
Corte dell'albero
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
9.6 out of 10, Exceptional, (133 reviews)
"A lovely room, hosts were extremely helpful, there some noise from the nearby kitchen, but this did not detract our enjoyment of our stay."
United Kingdom
Susan
The price is CA $138
CA $158 total
includes taxes & fees
Nov 7 - Nov 8
B&B Le Aquile
A historic building with intricate architectural details and a dome.

11. Guest House Bel Duomo

Guest House Bel Duomo
Historic Centre of Florence
8.6 out of 10, Excellent, (1,002 reviews)
"Great location and friendly staff! Would stay again."
United States
Tracy
The price is CA $89
CA $116 total
includes taxes & fees
Nov 15 - Nov 16
Guest House Bel Duomo
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 CA $190
CA $215 total
includes taxes & fees
Nov 10 - Nov 11
Blossoms of Siena
An outdoor courtyard with stone walls, arched doorways, and potted plants.

13. Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (205 reviews)
"This was one of the best places we stayed. We hiked the Tuscany portion of the Via Francegena and this stop was the best. The hotel is uniquely refurbished to include the 1,000 year old structures. It was an absolute delight. Blanca, was particularity helpful and accommodating. This is the best place to stay"
United States
Douglas
The price is CA $111
CA $130 total
includes taxes & fees
Oct 29 - Oct 30
Residenza d'Epoca Palazzo Buonaccorsi
A bedroom with a bed, a TV mounted on the wall, a window with a view of buildings, and a radiator.

14. Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (400 reviews)
"The room was fantastic & the staff above & beyond helpful & friendly."
United States
Clint
The price is CA $119
CA $153 total
includes taxes & fees
Nov 15 - Nov 16
Toscanelli Residenza D'epoca
A hotel room with a bed, a nightstand, a wall clock, and a framed picture on the wall.

15. Pier Capponi 17 Room & Suites

Pier Capponi 17 Room & Suites
Santissima Annunziata
9.6 out of 10, Exceptional, (37 reviews)
"Clean and beautiful room."
United States
Jennifer
The price is CA $94
CA $123 total
includes taxes & fees
Nov 26 - Nov 27
Pier Capponi 17 Room & Suites
A modern hotel room with a large bed, a built-in TV, a flat-screen TV on a stand, a bathroom with a bathtub, and a wooden floor.

16. Artemide GuestHouse

Artemide GuestHouse
Historic Centre of Florence
9.0 out of 10, Wonderful, (162 reviews)
"very good place close to the train station, short walk to the historic center and attractions"
Australia
Matthew
The price is CA $117
CA $147 total
includes taxes & fees
Nov 17 - Nov 18
Artemide GuestHouse
A balcony with a view of a pool and landscape, a wooden table with chairs, and a large umbrella.

17. Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (37 reviews)
"This was our second time staying here-- so charming and AMAZING breakfast❤️❤️❤️"
United States
Sasha
The price is CA $155
CA $177 total
includes taxes & fees
Nov 3 - Nov 4
Villa Sant Andrea
A hallway with a wooden door, two potted plants, and a doormat that reads "The Artists' Palace Florence".

18. The Artists' Palace Florence

The Artists' Palace Florence
Historic Centre of Florence
9.4 out of 10, Exceptional, (509 reviews)
"Location, staff, everything is amazing"
Canada
Maryam
The price is CA $142
CA $222 total
includes taxes & fees
Nov 8 - Nov 9
The Artists' Palace Florence
A bedroom with a bed, bedside tables, a bench, a sofa, and a radiator.

19. Residenza D'epoca Poliziano

Residenza D'epoca Poliziano
San Lorenzo
8.8 out of 10, Excellent, (73 reviews)
"Great location, clean, quiet"
United States
Charles
The price is CA $113
CA $143 total
includes taxes & fees
Nov 2 - Nov 3
Residenza D'epoca Poliziano
A stone building with multiple windows and a central entrance.

20. Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.4 out of 10, Exceptional, (62 reviews)
"I didn't see the staff, you have to follow instructions but it's pretty easy. The room was modern and updated. It was great!"
United States
Akis
The price is CA $90
CA $99 total
includes taxes & fees
Nov 11 - Nov 12
Fondaco del Moro
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
"We had a beautiful stay. Everything met our expectations. We will come back."
Ruben 3-night trip
Posted 10 hours ago
Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
2,673
Accommodation
8 Guest Houses
Lowest Price
CA $65
Highest Price
CA $394

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