Book The Best Hotels in Montegrossi for 2026 from CA $89 - Fully Refundable Options

Q: What's the top vacation rental in Montegrossi?

Borgo Argiano : This vacation home rental outside of Montegrossi is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library. See all vacation rentals in Montegrossi .

Q: What are some hotels with pools in Montegrossi?

Castello di Spaltenna- Small Luxury Hotels of the World : Offers an indoor pool, an outdoor pool, and 2 restaurants. Hotel Borgo di Cortefreda Relais and Four Points by Sheraton Siena are two additional hotels that feature an onsite pool. View all hotels with pools in Montegrossi .

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Our top choices for Montegrossi hotels

A spa area with a stone ceiling, a pool, and two sun loungers.

1. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

CA $122 total

includes taxes & fees

Dec 1 - Dec 2

A couple dining at an outdoor table with a view of the countryside.

2. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

CA $169 total

includes taxes & fees

Nov 23 - Nov 24

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

3. Agriturismo San Sano

Gaiole in Chianti

Glen

CA $173 total

includes taxes & fees

Nov 7 - Nov 8

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.

4. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

CA $111 total

includes taxes & fees

Nov 9 - Nov 10

A spacious lobby with a reception desk, seating area, and a large vase.

5. Hotel Valdarno

Montevarchi

Emmanuel

CA $171 total

includes taxes & fees

Nov 7 - Nov 8

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

6. Delta Hotel

Montevarchi

weixing

CA $184 total

includes taxes & fees

Nov 7 - Nov 8

A courtyard with stone flooring, arched walkways, and a central fountain.

7. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

CA $170 total

includes taxes & fees

Nov 8 - Nov 9

A person pouring a liquid from a bottle into a glass.

8. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

CA $172 total

includes taxes & fees

Nov 7 - Nov 8

A buffet with various food items and utensils.

9. Hotel Il Viandante

Terranuova Bracciolini

jessica

CA $175 total

includes taxes & fees

Nov 15 - Nov 16

A dining area with a table and chairs, a view of a landscape through an arched window, and a large umbrella providing shade.

10. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

CA $424 total

includes taxes & fees

Nov 9 - Nov 10

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

11. Hotel Villa Campomaggio

Radda in Chianti

Dario

CA $341 total

includes taxes & fees

Nov 7 - Nov 8

A modern building with a sign reading "Palace Hotel."

12. Palace Hotel Due Ponti

Due Ponti

Adam

CA $124 total

includes taxes & fees

Nov 27 - Nov 28

A rustic stone interior with a dining area, two armchairs, a table with a lamp, and a view through an arched doorway.

13. Castello di Volpaia

Radda in Chianti

Stenley

CA $328 total

includes taxes & fees

Dec 4 - Dec 5

An outdoor patio with tables and chairs, a pergola structure, and a stone building in the background.

14. Tenuta CorteDomina

Radda in Chianti

Edgar

CA $337 total

includes taxes & fees

Nov 9 - Nov 10

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

15. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

CA $407 total

includes taxes & fees

Nov 16 - Nov 17

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

16. Belvedere di San Leonino

Castellina in Chianti

Kevork

CA $175 total

includes taxes & fees

Nov 11 - Nov 12

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

17. Hotel Casafrassi

Castellina in Chianti

Stuart

CA $102 total

includes taxes & fees

Nov 18 - Nov 19

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

18. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Micaela

CA $253 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

19. Albergo Il Colombaio

Castellina in Chianti

Christine

CA $228 total

includes taxes & fees

Nov 7 - Nov 8

A pathway lined with trees and a large pot in the center.

20. Villa Montarioso

Montarioso

Michael

CA $134 total

includes taxes & fees

Nov 12 - Nov 13

View all properties

Top Montegrossi Hotel Reviews

Agriturismo San Sano

Gaiole in Chianti

10/10 Excellent

I can't believe this property is only a 2 star! The rooms are very basic, but they are very charming and just for sleeping and showering anyhow. We had no trouble sleeping, was quiet and comfortable. The breakfast was very good. The wine and food offered for purchase was affordable and very good. Staff was helpful and kind. We drove all over exploring the towns in Chanti. There's so many wineries if we had more time we would have booked a tour. The pool and views at this place are amazing....

Regan

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveller

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

Debbie

Castello di Volpaia

Radda in Chianti

10/10 Excellent

Stenley

Hotel Valdarno

Montevarchi

10/10 Excellent

Navjot

Hotel Il Viandante

Terranuova Bracciolini

10/10 Excellent

FRANCESCO

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jeremy

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

Palazzo di Valli

Siena

10/10 Excellent

We spent 2 days at the Palazzo do Vali and absolutely loved it!! Beautiful surroundings, magnificent home with frescoes on the ceiling and an old world charm! Sitting in the garden with a spectacular view of beautiful Siena was a perfect way to start our days with a delicious breakfast and also to end our days with some amazing italian red wine. Many thanks to Lorenzo and staff for making our stay unforgettable.

Chris&Susan

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

Hotel Ristorante La Dama nella Vigna

Monteriggioni

10/10 Excellent

mary christine

Frequently Asked Questions

What's the top vacation rental in Montegrossi?

Borgo Argiano: This vacation home rental outside of Montegrossi is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. You can relax into your vacation with a garden and a library. See all vacation rentals in Montegrossi.

If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?

Yes, the majority of hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.

Where can I learn more about changing or cancelling my trip to Montegrossi?

To find more details about rescheduling or cancelling your trip to Montegrossi, head over to our customer service page.

What are some hotels with pools in Montegrossi?

Castello di Spaltenna- Small Luxury Hotels of the World: Offers an indoor pool, an outdoor pool, and 2 restaurants. Hotel Borgo di Cortefreda Relais and Four Points by Sheraton Siena are two additional hotels that feature an onsite pool. View all hotels with pools in Montegrossi.

Find hotels in Montegrossi from CA $89

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

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Our top choices for Montegrossi hotels

1. Hotel Palazzo San niccolò & Spa

2. Palazzo Leopoldo Dimora Storica & Spa

3. Agriturismo San Sano

4. La Certosa di Pontignano - Place of Charme

5. Hotel Valdarno

6. Delta Hotel

7. Villa Casagrande Resort & SPA

8. Moody smart & comfy Hotel

9. Hotel Il Viandante

10. Chapter Chianti, a Member of Design Hotels

11. Hotel Villa Campomaggio

12. Palace Hotel Due Ponti

13. Castello di Volpaia

14. Tenuta CorteDomina

15. Dievole Wine Resort

16. Belvedere di San Leonino

17. Hotel Casafrassi

18. Castello di Fonterutoli Wine Resort

19. Albergo Il Colombaio

20. Villa Montarioso

Top Montegrossi Hotel Reviews

Agriturismo San Sano

10/10 Excellent

Frequently Asked Questions

What's the top vacation rental in Montegrossi?

If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?

Where can I learn more about changing or cancelling my trip to Montegrossi?

What are some hotels with pools in Montegrossi?

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