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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 Montegrossi bed & breakfast

Exterior detail
La Certosa di Pontignano

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (502)
"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is AED 301
AED 348 total
includes taxes & fees
11 Dec - 12 Dec
La Certosa di Pontignano
Garden
Arnolfo B&B

Arnolfo B&B

Arnolfo B&B
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (26)
"Stunning property in a cute hilltop town. Garden with tables and lounge chairs to have breakfast or hang out in the evenings. The rooms have nice details and good quality beds. "
France
Elsa
The price is AED 351
AED 394 total
includes taxes & fees
4 Jan - 5 January 2026
Arnolfo B&B
Interior
Antico Granaione

Antico Granaione

Antico Granaione
Rapolano Terme
9.8 out of 10, Exceptional, (59)
"old fashion building, clean and affordable"
United States
Irene
Antico Granaione
Exterior
B&B Country House Poggio del Drago

B&B Country House Poggio del Drago

B&B Country House Poggio del Drago
Civitella in Val di Chiana
9.8 out of 10, Exceptional, (57)
"Staff were friendly and helpful. Breakfast was just right - some fresh fruit would be nice to have. B&B was clean and tidy. Good signage so place was reasonably easy to find."
United States
Ludwig
B&B Country House Poggio del Drago
Porch
Il Chiostro del Carmine

Il Chiostro del Carmine

Il Chiostro del Carmine
Siena Historical Center
8.6 out of 10, Excellent, (870)
"Terrific place to stay. Breakfast was great, staff were friendly, and the view we had was stunning. Lots of room Old monastery was very interesting. "
Canada
John
Il Chiostro del Carmine
Basic Double Room, Private Bathroom | Down comforters, minibar, in-room safe, individually decorated
Quattro Cantoni

Quattro Cantoni

Quattro Cantoni
Siena City Centre
8.8 out of 10, Excellent, (80)
"Absolutely loved this stay. The staff were incredibly helpful and got me taxis etc when I needed them. The room was so comfortable with high tech support for working and relaxing. The meals were absolutely delicious and served with great customer service. This was a gem of a place to stay. The area is also beautiful and has much to offer in terms of a relaxing stay. I would happily go again! "
United Kingdom
Yvonne
The price is AED 295
AED 341 total
includes taxes & fees
23 Dec - 24 Dec
Quattro Cantoni
Exterior
Brolio Agriroom

Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti
8.8 out of 10, Excellent, (10)
"Ricasoli is stunning, and nice place to stay nearby"
United States
Arturo
Brolio Agriroom
Comfort Suite, 1 Bedroom, Non Smoking, Fireplace | Private kitchen | Microwave, stovetop, dishwasher, highchair
San Sebastiano Suite & Luxury

San Sebastiano Suite & Luxury

San Sebastiano Suite & Luxury
Colle di Val d'Elsa
8.6 out of 10, Excellent, (7)
"Great location and beautiful place to stay. Loved the interior decorating and host was good too. Would stay again. "
Canada
Nadia
San Sebastiano Suite & Luxury
Pool
Torrebianca Tuscany

Torrebianca Tuscany

Torrebianca Tuscany
Rignano sull'Arno
9.6 out of 10, Exceptional, (40)
"Lovely pool Breakfast good"
United Kingdom
christine
The price is AED 397
AED 443 total
includes taxes & fees
29 Dec - 30 Dec
Torrebianca Tuscany
Daily buffet breakfast (EUR 7.50 per person)
B&B San Francesco

B&B San Francesco

B&B San Francesco
Siena City Centre
9.4 out of 10, Exceptional, (46)
"Very nice enjoyable stay"
United States
Michael
B&B San Francesco
Front of property
A Casa Da Agata

A Casa Da Agata

A Casa Da Agata
Loro Ciuffenna
10.0 out of 10, Exceptional, (1)
"Our stay was aboslutely wonderful! The house and farm lies high up in the Tuscan hills and we were immersed in lush greenery with a river flowing nearby. Lorenzo was very welcoming and cooked us a delicious Tuscan dinner every night. We also loved his beautiful dog and two cats who made our stay extra nice! The room was sprakling clean and very cozy. "
United States
Carolina
The price is AED 490
AED 539 total
includes taxes & fees
11 Dec - 12 Dec
A Casa Da Agata
Free daily buffet breakfast
Casale La Gora

Casale La Gora

Casale La Gora
Figline e Incisa Valdarno
9.6 out of 10, Exceptional, (21)
"Casale La Gora in Tuscany. The property is beautifully renovated, blending historic charm with modern architecture. Our room was clean and cozy, the breakfast was delicious, and the pool was perfect for cooling off during the hot summer days. The host was warm, friendly, and always helpful, which made our stay even more enjoyable. We would definitely love to come back! "
Sweden
Besarta
The price is AED 330
AED 371 total
includes taxes & fees
19 Dec - 20 Dec
Casale La Gora
Free daily buffet breakfast
A Casa di BiaGio B&B

A Casa di BiaGio B&B

A Casa di BiaGio B&B
Rapolano Terme
10.0 out of 10, Exceptional, (24)
"It is an increable place to stay. Unbealiable very charm and cozy decoration, with everything you need. "
United States
Juan Diego
The price is AED 419
AED 478 total
includes taxes & fees
11 Dec - 12 Dec
A Casa di BiaGio B&B
Gazebo
Chiantirooms Guesthouse

Chiantirooms Guesthouse

Chiantirooms Guesthouse
Greve in Chianti
9.8 out of 10, Exceptional, (34)
"Friendly host and great place to stay. "
Canada
Pasquale
Chiantirooms Guesthouse
Outdoor pool, sun loungers
Relais Villa al Vento

Relais Villa al Vento

Relais Villa al Vento
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (78)
"The place was very welcoming and clean "
United States
SILVANO
The price is AED 394
AED 442 total
includes taxes & fees
18 Dec - 19 Dec
Relais Villa al Vento
Breakfast, lunch, dinner served; Italian cuisine, garden views
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (200)
"Clean room, courteous staff, and good winery"
United States
Sangchun
The price is AED 556
AED 629 total
includes taxes & fees
11 Dec - 12 Dec
Castello di Fonterutoli Wine Resort
Exterior detail
B&B Siena in Centro - Diffuso

B&B Siena in Centro - Diffuso

B&B Siena in Centro - Diffuso
Siena City Centre
8.6 out of 10, Excellent, (162)
"Great staff, good location and quiet"
United States
Molly
The price is AED 332
AED 382 total
includes taxes & fees
10 Jan - 11 January 2026
B&B Siena in Centro - Diffuso
Terrace/patio
Alle Terme B&B

Alle Terme B&B

Alle Terme B&B
Rapolano Terme
8.4 out of 10, Very Good, (20)
"We found the facility, very clean and the manager was very understanding and nice. A very nice asdortment of foods for breakfast was available. Would highly recommend this charming accomodation. "
United States
Cheryl
Alle Terme B&B
Garden
Villa Fiorita

Villa Fiorita

Villa Fiorita
Camollia
8.2 out of 10, Very Good, (183)
"Easy parking in the street behind the building. Amazing hosts Very close to city center and yet find parking."
United Kingdom
Kushal
The price is AED 235
AED 275 total
includes taxes & fees
7 Jan - 8 January 2026
Villa Fiorita
Interior
La Dimora Dei Monaci

La Dimora Dei Monaci

La Dimora Dei Monaci
Siena City Centre
10.0 out of 10, Exceptional, (86)
"Fantastic accommodations! Very comfortable bed! Spacious room, and beautiful. We definitely recommend."
United States
Karin
La Dimora Dei Monaci
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 Montegrossi Hotel Reviews

Villa del Sole Siena

Villa del Sole Siena

10/10 Excellent
"Amazing rooms and service!!"
Janet 1-night trip
Posted 2 days ago
Villa del Sole Siena

Frequently asked questions

Searching for B&Bs in Montegrossi?
If you want to find a place to stay with a small number of rooms and an intimate environment, a bed and breakfast might be a great fit for your trip to Montegrossi.
Why consider a B&B versus a traditional hotel?
Every B&B has its own unique feel. Whether it's a comfy common area with a fireplace or a beautiful dining room, the small details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Montegrossi?
Below are some well-liked B&Bs in the area: La Certosa di Pontignano: 9.1 mi (14.6 km) from the heart of Montegrossi. Enjoy the local cuisine breakfast and rooftop terrace. Castello di Fonterutoli Wine Resort: 15 rooms. 8.1 mi (13.1 km) from the downtown core. Enjoy the designer toiletries and winery. Borgo Del Cabreo: 11 rooms. Situated 10.4 mi (16.7 km) from the heart of Montegrossi. Enjoy the free buffet breakfast and winery. Il Chiostro del Carmine: 21 rooms. 13.2 mi (21.3 km) from the heart of downtown. Enjoy the free buffet breakfast and in-room dining. B&B San Francesco: 8 rooms. Located 12.6 mi (20.3 km) from the core of Montegrossi.
When should I stay at a B&B in Montegrossi?
When you're planning your getaway to Montegrossi, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Montegrossi is 37 inches.
How can I get to and around Montegrossi?
You can plan your excursions in and around Montegrossi ahead of time with these transportation options. Fly into Florence Airport, Peretola (FLR), which is located 25.5 mi (41.1 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.