Top 10 Hotels in Montegrossi (from $68) 2026 - Competitive Prices

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Our top choices for Montegrossi hotels

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

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

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

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

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

Gaiole in Chianti

Rama

$400 nightly

$452 total

Oct 5 - Oct 6

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.

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.

2. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

"Ultimo Mulino Hotel was amazing! The property is so peaceful and beautiful. We had breakfast both mornings and ate at their on site restaurant both evenings. The food was delicious and the staff was incredible. Leno was our server both nights- she was amazing and so helpful making suggestions on food and wines. We also enjoyed the spa for the wellness package and a couples massage for our honeymoon. We highly recommend this to everyone! It was so relaxing and worth the cost."

Hannah

$116 nightly

$137 total

Oct 6 - Oct 7

Total with taxes and fees

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

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

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

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

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

$279 nightly

$313 total

Oct 6 - Oct 7

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.

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

4. Villa Sassolini Country Boutique Hotel

Montevarchi

Peter

$210 nightly

$231 total

Oct 10 - Oct 11

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 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.

5. Relais Vignale & Spa

Radda in Chianti

Maaya

$205 nightly

$233 total

Oct 8 - Oct 9

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 stone building with a window and a light fixture.

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

6. Agriturismo San Sano

Gaiole in Chianti

Ernesto

$80 nightly

$93 total

Oct 11 - Oct 12

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.

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.

7. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

$120 nightly

$141 total

Oct 11 - Oct 12

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 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.

8. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

$185 nightly

$210 total

Oct 12 - Oct 13

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

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.

9. Podere L'Aquila

Gaiole in Chianti

$410 nightly

$456 total

Sep 16 - Sep 17

Total with taxes and fees

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

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

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

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

10. Tenuta CorteDomina

Radda in Chianti

Dustin

$236 nightly

$264 total

Oct 12 - Oct 13

Total with taxes and fees

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

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

A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

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

11. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Anthony

$372 nightly

$419 total

Sep 30 - Oct 1

Total with taxes and fees

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

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

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

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

12. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

$176 nightly

$200 total

Oct 12 - Oct 13

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.

13. Dievole Wine Resort

Castelnuovo Berardenga

Karamjit

$360 nightly

$406 total

Oct 11 - Oct 12

Total with taxes and fees

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

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

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

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

14. Hotel Casafrassi

Castellina in Chianti

Jane

$61 nightly

$68 total

Sep 20 - Sep 21

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.

15. Hotel Villa Campomaggio

Radda in Chianti

Krishna

$182 nightly

$207 total

Oct 12 - Oct 13

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

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

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

16. Palagina la Dimora

Figline e Incisa Valdarno

Tarek

$102 nightly

$115 total

Sep 14 - Sep 15

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 stone building with a wooden bench outside.

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

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

17. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

$112 nightly

$127 total

Sep 20 - Sep 21

Total with taxes and fees

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

A dining area with a table set for two, featuring wine bottles and bread.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

18. Castello La Leccia

Castellina in Chianti

Samuel

$268 nightly

$299 total

Oct 9 - Oct 10

Total with taxes and fees

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

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

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.

19. Hotel Valdarno

Montevarchi

Emmanuel

$111 nightly

$123 total

Sep 14 - Sep 15

Total with taxes and fees

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

A modern building with a glass facade, a car parked in front, and a well-lit entrance area.

A glass table with a sandwich and a drink, a yellow sofa, and a fireplace with flames.

A modern interior with a blue chair, a yellow chair, and a brown sofa. There is a glass door leading to an outdoor area with chairs and plants.

20. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

$105 nightly

$119 total

Oct 12 - Oct 13

Total with taxes and fees

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Top Montegrossi Hotel Reviews

Borgo Vescine

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."

Hotel Athena

8/10 Good

"Overall okay hotel. It’s meant more to come in during the morning while explore and out all day. Rooms are small and you can hear everything that’s going on in the hallway and in othe rooms (e.g., crying baby at 3am). Reception staff (Simone) was helpful and bartender (Lucas) was super nice. View in the terrace is good and peaceful but can’t be use if too close to dinner time."

NH Siena

10/10 Excellent

"Superior room not great, Very small with leaking shower and other issues. Upgraded to suite on 5th floor which was excellent. Very spacious, huge bathroom with bath and walk in shower. Great views and comfortable bed."

Villa Pitiana

10/10 Excellent

"We spent our honeymoon here and it was absolutely beautiful"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"All the staff in the hotel were very helpful and we would like to stay there again."

Hotel Chiusarelli

10/10 Excellent

"Great location. Wonderful staff, very helpful and polite."

Borgo San Felice Resort

10/10 Excellent

"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"

Fattoria di Vegi

10/10 Excellent

"Amazing! I wish I could have stayed forever!"

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

$96 nightly

$112 total

Sep 24 - Sep 25

Total with taxes and fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

$113 nightly

$130 total

Oct 11 - Oct 12

Total with taxes and fees

7.8/10 Good! (435 reviews)

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI

$158 nightly

$177 total

Oct 11 - Oct 12

Total with taxes and fees

9/10 Wonderful! (20 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

$157 nightly

$178 total

Oct 5 - Oct 6

Total with taxes and fees

8.8/10 Excellent! (106 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

$164 nightly

$186 total

Oct 11 - Oct 12

Total with taxes and fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

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 Grand Hotel Continental Siena – Starhotels Collezione. 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 Castello di Albola. You'll also find Castello di Radda Winery and Castle of Brolio 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 $68

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 Spaltenna- Small Luxury Hotels of the World

2. Ultimo Mulino Wellness Country Hotel

3. Chapter Chianti, a Member of Design Hotels

4. Villa Sassolini Country Boutique Hotel

5. Relais Vignale & Spa

6. Agriturismo San Sano

7. La Certosa di Pontignano

8. Palazzo Leopoldo Dimora Storica & Spa

9. Podere L'Aquila

10. Tenuta CorteDomina

11. Pieve Aldina - Relais & Châteaux

12. Hotel Palazzo San niccolò & Spa

13. Dievole Wine Resort

14. Hotel Casafrassi

15. Hotel Villa Campomaggio

16. Palagina la Dimora

17. Hotel Colle Etrusco Salivolpi

18. Castello La Leccia

19. Hotel Valdarno

20. Moody smart & comfy Hotel

Top Montegrossi Hotel Reviews

Borgo Vescine

Hotel Athena

NH Siena

Villa Pitiana

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

Borgo San Felice Resort

Fattoria di Vegi

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Antico Borgo Poggiarello

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Hotels in Montegrossi with star-rating

Frequently asked questions

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