Search Guest Houses in Chianti Region

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Check prices for these dates

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

Our top choices for Chianti Region guest houses

In-room dining
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 AED 314
AED 363 total
includes taxes & fees
14 Dec - 15 Dec
Casa di Palaia
Front of property
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
Restaurant
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
Garden
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 AED 330
AED 380 total
includes taxes & fees
17 Dec - 18 Dec
Villa Montarioso
1 bedroom, premium bedding, memory foam beds, minibar
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
Front of property
Agri Resort & Spa Le Colline del Paradiso

Agri Resort & Spa Le Colline del Paradiso

Agri Resort & Spa Le Colline del Paradiso
Vaglia
9.8 out of 10, Exceptional, (8)
"Lovely hotel in tranquil Tuscan setting. Clean room. Very nice restaurant. The best views. Would definitely recommend for a romantic trip away. "
United Kingdom
Rocco
Agri Resort & Spa Le Colline del Paradiso
Classic Double Room | Desk, blackout drapes, iron/ironing board, free WiFi
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 AED 450
AED 529 total
includes taxes & fees
17 Dec - 18 Dec
Tuscany View, Montalcino
Property grounds
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 AED 807
AED 910 total
includes taxes & fees
17 Dec - 18 Dec
Poggio Paradiso Resort & Spa
Exterior
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
Front of property
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
Exterior
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
Relais La Corte Dei Cavalieri
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
Terrace/patio
Blossoms of Siena

Blossoms of Siena

Blossoms of Siena
Siena City Centre
9.4 out of 10, Exceptional, (31)
"We really enjoyed our stay!! Everyone was accomodating and we loved Siena."
United States
Linda
The price is AED 561
AED 634 total
includes taxes & fees
10 Jan - 11 January 2026
Blossoms of Siena
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 AED 400
AED 457 total
includes taxes & fees
16 Dec - 17 Dec
Residenza d'Epoca San Martino 29
Terrace/patio
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 AED 346
AED 402 total
includes taxes & fees
12 Dec - 13 Dec
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
Free self parking
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
Exterior
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 AED 276
AED 304 total
includes taxes & fees
12 Dec - 13 Dec
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 AED 278
AED 305 total
includes taxes & fees
18 Dec - 19 Dec
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 3 days ago
Castello di Fonterutoli Wine Resort

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