Top 10 Hotels in Montegrossi (from $66) 2026 - Competitive Prices

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Our top choices for Montegrossi hotels

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone archway leading to a window with a view of tall trees and a distant landscape.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

1. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

$152 nightly

$176 total

Oct 26 - Oct 27

Total with taxes and fees

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

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

A stone building with a window and a light fixture.

2. Agriturismo San Sano

Gaiole in Chianti

Glen

$65 nightly

$76 total

Nov 2 - Nov 3

Total with taxes and fees

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

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

3. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

$110 nightly

$128 total

Nov 1 - Nov 2

Total with taxes and fees

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

A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

A courtyard with outdoor seating, stone walls, and a staircase.

A buffet area with various fruits and a bar with bottles.

4. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

$105 nightly

$123 total

Nov 2 - Nov 3

Total with taxes and fees

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

A table set with wine glasses and a candle, viewed through a window with string lights.

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

5. Tenuta CorteDomina

Radda in Chianti

Edgar

$123 nightly

$140 total

Nov 8 - Nov 9

Total with taxes and fees

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.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

An interior corridor with arches, columns, and a brick wall.

6. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Leslie

$90 nightly

$108 total

Oct 25 - Oct 26

Total with taxes and fees

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

A patio with a round table and chairs, potted plants, and a view of the building's interior.

A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.

A modern hotel lobby with a curved reception desk, seating area, and a bar.

7. Hotel Valdarno

Montevarchi

Emmanuel

$116 nightly

$127 total

Oct 24 - Oct 25

Total with taxes and fees

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

A historic building with a stone facade, arched entrance, and a wooden balcony.

A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

8. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

$99 nightly

$111 total

Nov 8 - Nov 9

Total with taxes and fees

An outdoor dining area with a pool, potted plants, and umbrellas.

A restaurant with a table set for two, overlooking a scenic landscape.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

9. Relais Vignale & Spa

Radda in Chianti

Ali

$198 nightly

$224 total

Oct 22 - Oct 23

Total with taxes and fees

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

A room with a view of a forest through a window, a table with a lamp, and a chair.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

10. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

$264 nightly

$299 total

Nov 7 - Nov 8

Total with taxes and fees

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

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

11. Hotel Villa Campomaggio

Radda in Chianti

Dario

$165 nightly

$188 total

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

12. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

$269 nightly

$302 total

Oct 11 - Oct 12

Total with taxes and fees

A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.

A cozy living room with a fireplace, wooden bookshelves, and a decorative mirror.

An outdoor dining area with tables and chairs, overlooking a scenic view of a coastal town during sunset.

An indoor dining area with tables set for two, large windows, and potted plants.

13. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

$203 nightly

$224 total

Oct 17 - Oct 18

Total with taxes and fees

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

14. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

$91 nightly

$109 total

Oct 18 - Oct 19

Total with taxes and fees

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

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

A modern reception area with a wooden reception desk, a metal bowl, potted plants, and a seating area with chairs.

15. Delta Hotel

Montevarchi

weixing

$114 nightly

$126 total

Oct 15 - Oct 16

Total with taxes and fees

A well-maintained garden with geometric hedges and a pathway leading to a building with multiple windows and outdoor seating.

A room with a large window offering a view of a vineyard and distant hills.

A restaurant with tables set for dining, large umbrellas, and a view of the landscape.

A cozy living room with a wooden ceiling, a television, a sofa, and a view of greenery outside.

16. Palagina la Dimora

Figline e Incisa Valdarno

Rayvant

$74 nightly

$83 total

Oct 12 - Oct 13

Total with taxes and fees

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.

A person relaxing in a hot tub with a view of a building and trees in the background.

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A poolside area with lounge chairs and a view of the night sky.

17. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

$121 nightly

$139 total

Oct 10 - Oct 11

Total with taxes and fees

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

A stone building with a garden, tall trees, and a clear blue sky.

A swimming pool with stone walls and a stone pathway leading to a building with multiple floors and a balcony.

18. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Sonja

$332 nightly

$376 total

Oct 30 - Oct 31

Total with taxes and fees

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

A stone house with a tiled roof, surrounded by greenery and a gravel path.

A rectangular swimming pool with a view of mountains in the background.

19. Podere L'Aquila

Gaiole in Chianti

Heather

$312 nightly

$352 total

Oct 10 - Oct 11

Total with taxes and fees

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

A clear blue pool with lounge chairs and a stone building in the background.

20. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

$107 nightly

$121 total

Oct 18 - Oct 19

Total with taxes and fees

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Top Montegrossi Hotel Reviews

Il Chiostro del Carmine

10/10 Excellent

"Amazing building, the breakfast was wonderful, the staff very friendly. The rooms could use some updating."

Hotel Borgo San Luigi

10/10 Excellent

"Beautiful hotel. Excellent food. The Staff was wonderful. We had an issue with our rental car passenger window and they did everything to help us with it."

Fattoria di Vegi

10/10 Excellent

"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

Hotel Minerva

10/10 Excellent

"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."

Villa Pitiana

10/10 Excellent

"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

$57 nightly

$66 total

Nov 4 - Nov 5

Total with taxes and fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

$75 nightly

$86 total

Nov 7 - Nov 8

Total with taxes and fees

7.8/10 Good! (450 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

$78 nightly

$89 total

Nov 4 - Nov 5

Total with taxes and fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

$95 nightly

$108 total

Nov 3 - Nov 4

Total with taxes and fees

8.8/10 Excellent! (111 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

$152 nightly

$172 total

Oct 19 - Oct 20

Total with taxes and fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

Hotels in Montegrossi with star-rating

Frequently asked questions

Where is the best place for a stay in Montegrossi?

Located 9.1 mi (14.6 km) from the heart of Montegrossi, La Certosa di Pontignano is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are Hotel Athena and Hotel Executive. See all available top hotels, or vacation rentals in Montegrossi.

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.

What's it like to stay in Montegrossi?

Visitors to Montegrossi are sure to find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodations to choose from. Find out more about Montegrossi.

What are the top places to visit in Montegrossi?

Places to visit in the wider area include Badia a Coltibuono, Meleto Castle, and Cantalici Winery. You'll also find Castello di Albola and Castello di Radda Winery in the area. Check out what more to see and do in Expedia's Montegrossi guide.

What's the seasonal weather like in Montegrossi?

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.

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Find hotels in Montegrossi from $66

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montegrossi hotels

1. Castello di Tornano Wine Resort

2. Agriturismo San Sano

3. Palazzo Leopoldo Dimora Storica & Spa

4. Hotel Palazzo San niccolò & Spa

5. Tenuta CorteDomina

6. La Certosa di Pontignano - Place of Charme

7. Hotel Valdarno

8. Villa Casagrande Resort & SPA

9. Relais Vignale & Spa

10. Dievole Wine Resort

11. Hotel Villa Campomaggio

12. Chapter Chianti, a Member of Design Hotels

13. Villa Sassolini Country Boutique Hotel

14. Ultimo Mulino Wellness Country Hotel

15. Delta Hotel

16. Palagina la Dimora

17. Belvedere di San Leonino

18. Castello di Spaltenna- Small Luxury Hotels of the World

19. Podere L'Aquila

20. Hotel Colle Etrusco Salivolpi

Top Montegrossi Hotel Reviews

Il Chiostro del Carmine

Hotel Borgo San Luigi

Fattoria di Vegi

Grand Hotel Continental Siena – Starhotels Collezione

Four Points by Sheraton Siena

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Hotel Minerva

Villa Pitiana

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Albergo Centrale

Castello di Bossi

Porta Pispini Residence

Hotels in Montegrossi with star-rating

Frequently asked questions

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