Search Guest Houses in Chianti Region

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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
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Jan 16 - Jan 18
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Feb 13 - Feb 15

Our top choices for Chianti Region guest houses

Exterior
Casa di Palaia

Casa di Palaia

Casa di Palaia
Greve in Chianti
10.0 out of 10, Exceptional, (22)
"Very well located in the heart if the Tuscany region."
United States
Eli
The price is ₩127,471
₩147,142 total
includes taxes & fees
Dec 21 - Dec 22
Casa di Palaia
Lobby
Dimora Casa Eugenia

Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (32)
"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
Dimora Casa Eugenia
Outdoor pool, open 8:00 AM to 7:30 PM, sun loungers
Borgo Nuovo San Martino

Borgo Nuovo San Martino

Borgo Nuovo San Martino
Bucine
6.8 out of 10, (10)
"Definitely going back in the summer"
United States
Josimar
Borgo Nuovo San Martino
Interior entrance
Homelink Poggibonsi

Homelink Poggibonsi

Homelink Poggibonsi
Barberino Tavarnelle
6.0 out of 10, (11)
"We didn't get the e-mail with the codes to the doors. The wifi doesn't connect to the internet. Our room wasn't cleaned during our stay. The place lokks abandoned from the inside. The room wasclean when we arrived. The inside of the place looks nice. "
Denmark
Kaya
Homelink Poggibonsi
Garden
Villa Montarioso

Villa Montarioso

Villa Montarioso
Montarioso
8.6 out of 10, Excellent, (134)
"Quiet location not far from Siena. Has free parking and free light breakfast. "
United States
Aileen
The price is ₩174,738
₩199,136 total
includes taxes & fees
Dec 28 - Dec 29
Villa Montarioso
Courtyard
Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi

Residenza d'Epoca Palazzo Buonaccorsi
San Gimignano City Centre
8.6 out of 10, Excellent, (171)
"Exceptional building and excellent staff "
Canada
Mariana
The price is ₩141,635
₩164,454 total
includes taxes & fees
Dec 21 - Dec 22
Residenza d'Epoca Palazzo Buonaccorsi
Comfort Double Room | Terrace/patio
Villa Gelsomino Garden

Villa Gelsomino Garden

Villa Gelsomino Garden
Oltrarno
9.0 out of 10, Wonderful, (129)
"Great clean hotel not far from central Florence. "
United States
David
Villa Gelsomino Garden
Classic Double Room | Living area | 25-inch flat-screen TV with satellite channels, TV
Tuscany View, Montalcino

Tuscany View, Montalcino

Tuscany View, Montalcino
Montalcino
8.6 out of 10, Excellent, (8)
"Very nice place right in town convenient to everything"
United States
Bonnie
The price is ₩201,915
₩235,955 total
includes taxes & fees
Dec 21 - Dec 22
Tuscany View, Montalcino
Reception
Villa Sant Andrea

Villa Sant Andrea

Villa Sant Andrea
Siena
9.2 out of 10, Wonderful, (33)
"Nice Tuscan Villa, only 10 minutes from city centre, easy parking and moving in and out of the city. The host are great, Cecilia and husband always available to help."
United States
Adrian
Villa Sant Andrea
Lobby sitting area
Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (14)
"Excellent room and food. Great location!"
United States
Saurabh
The price is ₩395,729
₩444,477 total
includes taxes & fees
Dec 29 - Dec 30
Poggio Paradiso Resort & Spa
Luxury Double or Twin Room | Premium bedding, memory foam beds, individually decorated
Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile

Residenza d'Epoca Le Aquile
Siena City Centre
10.0 out of 10, Exceptional, (83)
"Beautiful area, very walkable! "
United States
Anita
Residenza d'Epoca Le Aquile
Minibar, desk, iron/ironing board, free WiFi
Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri

Relais La Corte Dei Cavalieri
Siena City Centre
8.0 out of 10, Very Good, (89)
"Nice and easy checking friendly staff "
United States
Jose
Relais La Corte Dei Cavalieri
Exterior
B&B Le Aquile

B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (111)
"Staff was exceptionally helpful prior to arriving at property and offering suggestions for transportation to surrounding activities. Location was well situated to highlights and attractions. "
Canada
Lydia
B&B Le Aquile
Hallway
Blossoms of Siena

Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (32)
"We really enjoyed our stay!! Everyone was accomodating and we loved Siena."
United States
Linda
The price is ₩227,466
₩257,137 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Blossoms of Siena
Deluxe Room | Premium bedding, in-room safe, individually decorated, desk
Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29

Residenza d'Epoca San Martino 29
Siena City Centre
9.8 out of 10, Exceptional, (30)
"The host was very friendly and helpful. We had a great stay."
United States
Anonymous traveler
The price is ₩171,761
₩195,861 total
includes taxes & fees
Dec 22 - Dec 23
Residenza d'Epoca San Martino 29
Exterior
AmiRooms Affittacamere

AmiRooms Affittacamere

AmiRooms Affittacamere
Siena City Centre
10.0 out of 10, Exceptional, (9)
"Thanks to Amina, very welcoming. "
Canada
daniel
AmiRooms Affittacamere
Exterior
Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house
San Gimignano City Centre
9.8 out of 10, Exceptional, (6)
The price is ₩171,379
₩197,172 total
includes taxes & fees
Dec 20 - Dec 21
Duccio Nacci Rooms - guest house
Double Room (Il Nido) | Pillowtop beds, blackout drapes, free WiFi, bed sheets
Il Sogno di Annalisa

Il Sogno di Annalisa

Il Sogno di Annalisa
Volterra
8.0 out of 10, Very Good, (15)
"Lovely property inside the city walls but away from the high traffic tourist areas. Well equipped with everything you need. Easy check in. We had a lovely visit in Volterra."
United States
Sylvia
Il Sogno di Annalisa
Courtyard
L'Antico Borgo di Torri

L'Antico Borgo di Torri

L'Antico Borgo di Torri
Sovicille
8.0 out of 10, Very Good, (1)
"Appartamento confortevole, Lorenzo oste disponibile e molto simpatico. Faceva molto caldo e l'aria condizionata sarebbe gradita. Borgo piccolo ma interessante, ottimo ristorante vicinissimo. Ci torneremo!"
Italy
Anonymous traveler
L'Antico Borgo di Torri
Single Room, 1 Twin Bed, Private Bathroom, City View | View from room
B&B San Francesco

B&B San Francesco

B&B San Francesco
Cortona Old Town
8.8 out of 10, Excellent, (55)
"The B&B is charming, the location is perfect, and Beatrice and the staff are so nice!"
United States
Maria
B&B San Francesco
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

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

10/10 Excellent
"Very clean,staff was very kind and helpful. Looking forward to come back! 😊"
Andrea 2-night trip
Posted 11 days ago
Castello di Fonterutoli Wine Resort

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
971
Accommodation
9 Guest Houses
Lowest Price
₩147,142
Highest Price
₩444,477