Best B&B Montegrossi in 2026

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Our top choices for Montegrossi bed & breakfast

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

1. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

₹7,551 total

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a stone wall, a bed, a nightstand, a window, and a mirror.

2. Casale La Gora

Figline e Incisa Valdarno

Roberto

₹7,202 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with a tiled roof, surrounded by greenery and a clear sky.

3. Brolio Agriroom

Gaiole in Chianti

Arturo

₹10,567 total

includes taxes & fees

7 Nov - 8 Nov

A narrow stone pathway leading to a rustic building with a wooden door and a window.

4. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

₹17,301 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor dining area with a table and chairs, surrounded by greenery and a view of a building in the background.

5. Chiantirooms Guesthouse

Greve in Chianti

Pasquale

₹11,006 total

includes taxes & fees

12 Nov - 13 Nov

A wooden chair and table with a bottle and wine glass.

6. B&B Poggiobonizio

Poggibonsi

ROBERT

₹6,874 total

includes taxes & fees

7 Dec - 8 Dec

An outdoor dining area with a table and chairs, a potted plant, and a stone building with a balcony.

7. A Casa Da Agata

Loro Ciuffenna

Carolina

₹13,642 total

includes taxes & fees

1 Dec - 2 Dec

A kitchen with a brick archway, a wooden table with pies, and a clock on the wall.

8. A Casa di BiaGio B&B

Rapolano Terme

Juan Diego

₹10,591 total

includes taxes & fees

12 Nov - 13 Nov

A stone building with outdoor seating and a pool in the background.

9. B&B Country House Poggio del Drago

Civitella in Val di Chiana

Kristen

₹13,455 total

includes taxes & fees

25 Nov - 26 Nov

An outdoor patio with tables and chairs, string lights, and hanging glass globes.

10. Bed & Breakfast Le Terrazze del Chianti

Tavarnelle Val di Pesa

Janine und Thomas

₹9,567 total

includes taxes & fees

3 Dec - 4 Dec

A dining area with a wooden table, chairs, a vase with sunflowers, and a wooden cabinet with glass doors.

11. A'Loro B&B

Terranuova Bracciolini

Emiliano

₹14,931 total

includes taxes & fees

12 Nov - 13 Nov

A neatly made bed with two pillows, a bedside lamp, and a nightstand.

12. Alle Terme B&B

Rapolano Terme

Cheryl

₹9,246 total

includes taxes & fees

11 Nov - 12 Nov

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

13. Relais degli Angeli

Siena City Centre

Manjeet

₹12,706 total

includes taxes & fees

1 Dec - 2 Dec

An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

14. Torrebianca Tuscany

Rignano sull'Arno

Roberto

₹8,893 total

includes taxes & fees

8 Nov - 9 Nov

A historic building with multiple stories, green shutters, and a visible entrance.

15. B&B San Francesco

Siena City Centre

Albert

₹6,969 total

includes taxes & fees

30 Nov - 1 Dec

A large, two-story building with a symmetrical facade, a central entrance with a staircase, and a well-maintained lawn with a circular garden feature.

16. Relais Villa al Vento

Figline e Incisa Valdarno

Ian

₹12,623 total

includes taxes & fees

17 Nov - 18 Nov

A narrow hallway leading to a bedroom with a four-poster bed, a wooden wardrobe, and a chandelier.

17. All'Ombra della Torre

Siena City Centre

"The location was perfect, easy walk from parking and easy walk to all the sites. The check in is completely online and there are no onsite staff. If you message the staff are responsive. The bedroom was great and cool, although no air on. The shared bathroom was large, but shower could have been better cleaned and maintained. Although the name suggests it is a bed & breakfast, there is no breakfast included, however, there are plenty of cafes just downstairs."

William

₹6,350 total

includes taxes & fees

12 Nov - 13 Nov

A courtyard with a stone building featuring green shutters, surrounded by a lush green landscape and trees.

18. Arnolfo B&B

Colle di Val d'Elsa

Elsa

₹8,828 total

includes taxes & fees

9 Nov - 10 Nov

A covered outdoor seating area with white wicker furniture, a table with a vase of flowers, and two candelabras.

19. Country Lodge

Petriccio

Ellen

₹14,549 total

includes taxes & fees

17 Nov - 18 Nov

An outdoor dining area with wicker furniture, a table set with croissants, a bowl of fruit, and a glass of orange juice.

20. Il Chiostro del Carmine

Siena Historical Center

Edward

₹11,624 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Top reviews in Montegrossi

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

This place is surreal. We felt like we were on the set of the Name of the Rose. Sleeping in a real XIV century monastery, with its own church (with amazing frescoes), on a hill overlooking the grapes and olive trees dotted countryside...just unbelievable. We stay in one the celle, which is a 3 bedroom apartment on 2 floors, with your own private garden...yes, that's correct. Simply unheard of. The location is great too (Siena is a short drive away). The only setbacks were breakfast, very...

Ivo

Castello di Fonterutoli Wine Resort

Castellina in Chianti

10/10 Excellent

Claire

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Excellent

My husband and I had a wonderful stay at Poggio del Drago - Emanuele is a perfect host and made us feel very welcome throughout our stay. The room itself was lovely - recently renovated and looking lovely. The pool is perfectly located, overlooking the olive groves and with plenty of loungers for all guests. Breakfast was great - a large breakfast table where all guests sat together and took breakfast - an array of sliced meats, cereals, and also a coffee machine to make yourself a cappuccino or...

katy

Bed & Breakfast Le Terrazze del Chianti

Tavarnelle Val di Pesa

10/10 Excellent

Raymond

Relais degli Angeli

Siena City Centre

10/10 Excellent

Olivia

B&B Poggiobonizio

Poggibonsi

10/10 Excellent

ROBERT

A'Loro B&B

Terranuova Bracciolini

10/10 Excellent

Emiliano

Antica Residenza Cicogna

Siena City Centre

10/10 Excellent

Matthew

A room with a piano, stone walls, a wooden cabinet, and a bench.

Antico Granaione

Rapolano Terme

10/10 Excellent

Caroline

Relais Villa al Vento

Figline e Incisa Valdarno

10/10 Excellent

Me and my partner stayed here for 3 nights and from a 3 week stay across Italy, it was the highlight of our trip. The Villa is gorgeous, the rooms are spacious, comfy and clean. Breakfast is lovely and plenty of option, they’ll even make a lovely omelette if you’d like one. The pool is amazing and has views that are out of this world. Only downside is the location and having to get the bus into/out of Florence everyday but very grateful to the owner and her daughter for the lifts they gave us to...

Laura

B&B San Francesco

Siena City Centre

10/10 Excellent

Katherine

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

La Dimora Dei Monaci

Siena City Centre

10/10 Excellent

Katharine

Frequently Asked Questions

Searching for B&Bs in Montegrossi?

If you're looking for some accommodation with fewer rooms than the traditional hotel and a more personalised environment, a bed and breakfast might be a great fit for your trip to Montegrossi.

Why consider B&Bs instead of traditional hotels?

Every B&B has its own unique feel — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a fun place to get away.

What are the best B&Bs in Montegrossi?

Below are some well-liked B&Bs in the surrounding area: La Certosa di Pontignano: 9.1 mi (14.6 km) from the heart of Montegrossi. Enjoy the rooftop terrace and snack bar/deli. Il Chiostro del Carmine: 21 rooms. 13.2 mi (21.3 km) from the city centre. Enjoy the free buffet breakfast and in-room dining. Relais degli Angeli: 7 rooms. Situated 12.7 mi (20.4 km) from the heart of Montegrossi. Enjoy the rooftop terrace and unique decor. Borgo Del Cabreo: 11 rooms. 10.4 mi (16.7 km) from the city centre. Enjoy the free buffet breakfast and winery. Castello di Fonterutoli Wine Resort: 15 rooms. Located 8.1 mi (13.1 km) from the core of Montegrossi. Enjoy the designer toiletries and winery.

What's the best time of year to stay at a B&B in Montegrossi?

When you're planning your getaway to Montegrossi, make sure that you take the year-round temperatures into account. The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montegrossi is 946 mm.

How can I get to and around Montegrossi?

You can map out your trip in and around Montegrossi ahead of time with these transportation options. Fly into Peretola Airport (FLR), which is located 25.5 mi (41.1 km) away from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.

Search Bed and Breakfasts in Montegrossi

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montegrossi bed & breakfast

1. La Certosa di Pontignano - Place of Charme

2. Casale La Gora

3. Brolio Agriroom

4. Castello di Fonterutoli Wine Resort

5. Chiantirooms Guesthouse

6. B&B Poggiobonizio

7. A Casa Da Agata

8. A Casa di BiaGio B&B

9. B&B Country House Poggio del Drago

10. Bed & Breakfast Le Terrazze del Chianti

11. A'Loro B&B

12. Alle Terme B&B

13. Relais degli Angeli

14. Torrebianca Tuscany

15. B&B San Francesco

16. Relais Villa al Vento

17. All'Ombra della Torre

18. Arnolfo B&B

19. Country Lodge

20. Il Chiostro del Carmine

Top reviews in Montegrossi

La Certosa di Pontignano - Place of Charme

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Montegrossi?

Why consider B&Bs instead of traditional hotels?

What are the best B&Bs in Montegrossi?

What's the best time of year to stay at a B&B in Montegrossi?

How can I get to and around Montegrossi?

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