Top 10 Hotels in Montegrossi (from $62) 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 stone building with a tower, surrounded by people dining at tables with candles.

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.

1. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

$142 nightly

$165 total

Oct 29 - Oct 30

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

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

A stone building with a window and a light fixture.

2. Agriturismo San Sano

Gaiole in Chianti

Glen

$66 nightly

$77 total

Oct 18 - Oct 19

Total with taxes and fees

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

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

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

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

3. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

$94 nightly

$112 total

Oct 22 - Oct 23

Total with taxes and fees

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

A villa with a swimming pool, outdoor seating, and a garden.

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

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

4. Relais Vignale & Spa

Radda in Chianti

Ali

$187 nightly

$212 total

Oct 26 - Oct 27

Total with taxes and fees

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

A narrow street with buildings on either side, a flag, and a bench.

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

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

5. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

$117 nightly

$135 total

Nov 2 - Nov 3

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 corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

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.

6. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

$89 nightly

$107 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

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.

7. Hotel Villa Campomaggio

Radda in Chianti

Dario

$139 nightly

$160 total

Nov 3 - Nov 4

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 modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

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

$112 nightly

$125 total

Nov 2 - Nov 3

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 a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.

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

9. Hotel Valdarno

Montevarchi

Emmanuel

$114 nightly

$125 total

Oct 8 - Oct 9

Total with taxes and fees

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

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

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

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

10. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

$292 nightly

$330 total

Oct 27 - Oct 28

Total with taxes and fees

A bottle of Bagnio Doccia al Vino Rosso on a rustic stone ledge with a glass.

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

A building with a brick facade, arched entrance, and multiple windows covered in green ivy.

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

11. Tenuta CorteDomina

Radda in Chianti

Edgar

$236 nightly

$264 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

A four-poster bed with a view of the outdoors, a desk with a chair, and a sofa in a room with wooden beams on the ceiling.

12. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

$203 nightly

$224 total

Oct 5 - Oct 6

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 buffet area with various fruits and a bar with bottles.

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

13. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

$123 nightly

$142 total

Nov 1 - Nov 2

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 hotel room with a bed, a TV, a desk, and a mirror.

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

14. Delta Hotel

Montevarchi

weixing

$108 nightly

$119 total

Oct 5 - Oct 6

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

A stone building with a wooden bench outside.

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

15. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

$101 nightly

$114 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

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

A modern living room with a white sofa, armchairs, and a coffee table.

16. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

$270 nightly

$304 total

Oct 6 - Oct 7

Total with taxes and fees

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

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

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

A stone building with a balcony, potted plants, and a view of distant hills.

17. Podere L'Aquila

Gaiole in Chianti

Heather

$393 nightly

$437 total

Oct 7 - Oct 8

Total with taxes and fees

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

A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

18. Hotel Casafrassi

Castellina in Chianti

Rita

$60 nightly

$73 total

Oct 6 - Oct 7

Total with taxes and fees

A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

A stone building with a rustic exterior, surrounded by lush greenery and outdoor seating areas.

An outdoor patio area with tables and chairs, a reception desk, and potted plants.

A view from a covered outdoor area with a paved floor, leading to a garden with various plants and a distant landscape.

19. Hotel Villa San Giorgio

Poggibonsi

Arik

$62 nightly

$68 total

Nov 3 - Nov 4

Total with taxes and fees

A stone building with arched windows, a grassy courtyard, and outdoor seating.

A person relaxing in a clear pool surrounded by natural scenery.

A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

20. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

$361 nightly

$406 total

Oct 22 - Oct 23

Total with taxes and fees

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Top Montegrossi Hotel Reviews

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"This hotel was PERFECT for our honeymoon trip to Siena. It was peaceful and quiet, but still close enough to get to the city centre and the train station easily. The pool was a perfect oasis after hot days. The staff were so friendly and helpful. The terrace was a gorgeous place for a night cap at the end of the night. We would definitely stay here again."

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 Borgo San Luigi

8/10 Good

"Great breakfast and clean room. However, not a very kid friendly with no high chair available in the room and the few ones in the restaurant were broken or dirty. Good place for adulte."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"A peaceful luxurious stay with amazing amenities, 6 star service & and amazing dinner restaurant."

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Hotel Athena

10/10 Excellent

"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."

La Certosa di Pontignano

10/10 Excellent

"good to stay"

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."

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

$54 nightly

$62 total

Nov 1 - Nov 2

Total with taxes and fees

7.8/10 Good! (258 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

$92 nightly

$104 total

Nov 3 - Nov 4

Total with taxes and fees

8.8/10 Excellent! (108 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

$93 nightly

$105 total

Nov 3 - Nov 4

Total with taxes and fees

10/10 Exceptional! (50 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

$102 nightly

$115 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (445 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

$152 nightly

$173 total

Oct 20 - Oct 21

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 $62

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. Ultimo Mulino Wellness Country Hotel

4. Relais Vignale & Spa

5. Palazzo Leopoldo Dimora Storica & Spa

6. La Certosa di Pontignano

7. Hotel Villa Campomaggio

8. Villa Casagrande Resort & SPA

9. Hotel Valdarno

10. Dievole Wine Resort

11. Tenuta CorteDomina

12. Villa Sassolini Country Boutique Hotel

13. Hotel Palazzo San niccolò & Spa

14. Delta Hotel

15. Hotel Colle Etrusco Salivolpi

16. Chapter Chianti, a Member of Design Hotels

17. Podere L'Aquila

18. Hotel Casafrassi

19. Hotel Villa San Giorgio

20. Pieve Aldina - Relais & Châteaux

Top Montegrossi Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Hotel Borgo San Luigi

Borgo Scopeto Wine & Country Relais

Fattoria di Vegi

Hotel Athena

La Certosa di Pontignano

Hotel Minerva

More cheap stays in Montegrossi

Cannon d'Oro

Albergo Centrale

Torre del Fuggisole

Piccolo Hotel Etruria

Castello di Bossi

Porta Pispini Residence

Hotels in Montegrossi with star-rating

Frequently asked questions

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