Search Guest Houses in Chianti Region

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 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 Rp1.444.273
Rp1.667.154 total
includes taxes & fees
24 Dec - 25 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)
"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
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
Deluxe Quadruple Room | 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 Rp1.155.886
Rp1.506.838 total
includes taxes & fees
25 Dec - 26 Dec
Palazzo Oliveto
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 Rp1.979.805
Rp2.256.239 total
includes taxes & fees
2 Jan - 3 Jan 2026
Villa Montarioso
Standard Double Room, City View (Tornabuoni Small Size Room) | Premium bedding, in-room safe, soundproofing, free WiFi
Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca

Toscanelli Residenza D'epoca
Historic Centre of Florence
9.6 out of 10, Exceptional, (366)
"Great location with lots of sights and restaurants in walklng distance. "
Ireland
jennifer
The price is Rp1.540.558
Rp1.969.204 total
includes taxes & fees
19 Jan - 20 Jan 2026
Toscanelli Residenza D'epoca
Classic Double Room | Desk, blackout curtains, 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 Rp2.287.728
Rp2.673.409 total
includes taxes & fees
24 Dec - 25 Dec
Tuscany View, Montalcino
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
Property grounds
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 Rp4.483.665
Rp5.035.984 total
includes taxes & fees
29 Dec - 30 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
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 traveller
The price is Rp2.103.824
Rp2.392.660 total
includes taxes & fees
7 Jan - 8 Jan 2026
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
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, (89)
"Nice and easy checking friendly staff "
United States
Jose
Relais La Corte Dei Cavalieri
Terrace/patio
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 Rp2.577.225
Rp2.913.401 total
includes taxes & fees
7 Jan - 8 Jan 2026
Blossoms of Siena
Double Room (Il Nido) | Pillow-top beds, blackout curtains, 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
Exterior
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 Rp1.765.222
Rp2.039.812 total
includes taxes & fees
26 Dec - 27 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 traveller
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 3 weeks ago
Hotel Borgo di Cortefreda Relais

Find out more about Chianti Region

Chianti Region Guest Houses information

Number of reviews
1,293
Accommodation
9 Guest Houses
Lowest Price
Rp1.506.838
Highest Price
Rp5.035.984