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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

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 ₩127,345
₩146,997 total
includes taxes & fees
Dec 16 - Dec 17
Casa di Palaia
Lobby
Dimora Casa Eugenia

Dimora Casa Eugenia

Dimora Casa Eugenia
Loro Ciuffenna
9.2 out of 10, Wonderful, (32)
"Nice hotel, beautiful large room. Nice view over the river. "
Norway
Hilde Stendal
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 ₩174,565
₩198,939 total
includes taxes & fees
Dec 25 - Dec 26
Villa Montarioso
Hypo-allergenic bedding, minibar, in-room safe, free WiFi
Palazzo Oliveto

Palazzo Oliveto

Palazzo Oliveto
Oltrarno
7.6 out of 10, Good, (90)
"Great service easy check in Clean safe quiet "
United States
Gabriel
The price is ₩95,890
₩126,232 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo Oliveto
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
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 ₩201,716
₩235,723 total
includes taxes & fees
Dec 25 - Dec 26
Tuscany View, Montalcino
Lobby sitting area
Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (13)
"Excellent room and food. Great location!"
United States
Saurabh
The price is ₩327,879
₩369,861 total
includes taxes & fees
Dec 15 - Dec 16
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, (88)
"Nice and easy checking friendly staff "
United States
Jose
The price is ₩156,824
₩179,425 total
includes taxes & fees
Dec 29 - Dec 30
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 ₩227,954
₩257,688 total
includes taxes & fees
Jan 8 - Jan 9, 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 ₩196,940
₩223,573 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza d'Epoca San Martino 29
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
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 ₩141,939
₩164,807 total
includes taxes & fees
Dec 14 - Dec 15
Residenza d'Epoca Palazzo Buonaccorsi
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
Breakfast area
Fondaco del Moro

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (33)
"Excellent breakfast, clean, quiet room. "
United States
Sheily
The price is ₩111,782
₩122,960 total
includes taxes & fees
Dec 14 - Dec 15
Fondaco del Moro
3 restaurants, dinner served, Italian cuisine
Palazzo Ninci

Palazzo Ninci

Palazzo Ninci
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (7)
"Stanza molto curata ma c'era una vibrazione nel muro, che da quanto ho capito era una pompa che caricava l'acqua del bagno. Per il resto era ok"
Italy
Luigi Cesario
The price is ₩116,341
₩127,975 total
includes taxes & fees
Dec 16 - Dec 17
Palazzo Ninci
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 5 days ago
Castello di Fonterutoli Wine Resort

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
954
Accommodation
9 Guest Houses
Lowest Price
₩122,960
Highest Price
₩369,861

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