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Oct 11 - Oct 12
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Oct 12 - Oct 13
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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 restaurant with stone walls and a high ceiling, featuring tables set for dining.
A sunlit patio with a glass roof, stone walls, and outdoor seating.
A stone building with a garden, tall trees, and a clear blue sky.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
Canada
Sonja
NT$10,533
NT$11,943 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
An outdoor dining area with a pool, potted plants, and umbrellas.
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.
A restaurant with a table set for two, overlooking a scenic landscape.

2. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
NT$5,513
NT$7,162 total
includes taxes & fees
Oct 19 - Oct 20
Relais Vignale & Spa
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 narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

3. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
Canada
Marissa
NT$8,690
NT$9,845 total
includes taxes & fees
Nov 9 - Nov 10
Dievole Wine Resort
A couple dining at an outdoor table with a view of the countryside.
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A narrow street with buildings on either side, a flag, and a bench.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

4. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
NT$3,518
NT$4,084 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Leopoldo Dimora Storica & Spa
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 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.

5. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
NT$3,803
NT$4,184 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Valdarno
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
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.
A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

6. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Dario
NT$5,266
NT$6,008 total
includes taxes & fees
Nov 3 - Nov 4
Hotel Villa Campomaggio
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.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A modern living room with a white sofa, armchairs, and a coffee table.

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
NT$8,582
NT$9,655 total
includes taxes & fees
Oct 12 - Oct 13
Chapter Chianti, a Member of Design Hotels
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 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.

8. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
United States
Edgar
NT$3,922
NT$4,457 total
includes taxes & fees
Nov 8 - Nov 9
Tenuta CorteDomina
A spa area with a stone ceiling, a pool, and two sun loungers.
A courtyard with outdoor seating, stone walls, and a staircase.
A buffet area with various fruits and a bar with bottles.
A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

9. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
United States
Afeefa
NT$3,102
NT$3,627 total
includes taxes & fees
Nov 11 - Nov 12
Hotel Palazzo San niccolò & Spa
A large building with multiple rooms, surrounded by a field of lavender.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
An arched brick corridor leading to a dining area with tables set for a meal.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

10. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
NT$12,318
NT$13,908 total
includes taxes & fees
Nov 6 - Nov 7
Borgo Scopeto Wine & Country Relais
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.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.

11. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
United States
Lisa
NT$4,853
NT$5,624 total
includes taxes & fees
Oct 25 - Oct 26
Castello di Tornano Wine Resort
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.

12. Delta Hotel

Delta Hotel
Montevarchi
United States
weixing
NT$4,096
NT$4,506 total
includes taxes & fees
Oct 14 - Oct 15
Delta Hotel
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

13. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
NT$17,508
NT$19,616 total
includes taxes & fees
Oct 21 - Oct 22
Hotel Le Fontanelle
A poolside area with a view of a mountainous landscape, a well-manicured lawn, and outdoor seating with umbrellas.
An indoor dining area with tables set for two, large windows, and potted plants.
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.

14. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
United Kingdom
Peter
NT$7,103
NT$7,813 total
includes taxes & fees
Oct 12 - Oct 13
Villa Sassolini Country Boutique Hotel
A bathroom with a bathtub, tiled walls, and a towel hanging on the wall.
A pool area with lounge chairs and a service person attending to a guest.
A historic stone building with multiple windows and a courtyard.
A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

15. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
NT$24,121
NT$26,891 total
includes taxes & fees
Nov 7 - Nov 8
Borgo San Felice Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

16. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
NT$14,921
NT$16,700 total
includes taxes & fees
Nov 4 - Nov 5
Borgo Vescine
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.
A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.
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.

17. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Ana
NT$3,448
NT$3,864 total
includes taxes & fees
Nov 8 - Nov 9
Villa Casagrande Resort & SPA
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

18. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
NT$11,398
NT$12,896 total
includes taxes & fees
Nov 1 - Nov 2
The Club House
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 bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

19. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
Canada
Ariel
NT$2,898
NT$3,473 total
includes taxes & fees
Oct 22 - Oct 23
Ultimo Mulino Wellness Country Hotel
A stone building with arched windows, a grassy courtyard, and outdoor seating.
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.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

20. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
NT$11,095
NT$12,491 total
includes taxes & fees
Oct 22 - Oct 23
Pieve Aldina - Relais & Châteaux
View all properties

Hotels recommended for families in Montegrossi

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 sunlit patio with a glass roof, stone walls, and outdoor seating.
A stone building with a garden, tall trees, and a clear blue sky.

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
NT$10,533
NT$11,943 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
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.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A modern living room with a white sofa, armchairs, and a coffee table.

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
NT$8,582
NT$9,655 total
includes taxes & fees
Oct 12 - Oct 13
Chapter Chianti, a Member of Design Hotels
A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.
A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.
A pool with a view of a mountainous landscape and a village in the background.
A dining area with a table set for a meal, a fireplace, and a wooden ceiling.

Cavarchino B&B

Cavarchino B&B
Gaiole in Chianti
NT$4,750
NT$5,511 total
includes taxes & fees
Nov 1 - Nov 2
Cavarchino B&B
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A pathway leading to a pool area with lounge chairs and umbrellas.
A stone building with a clear view of a lush green landscape, including trees and a distant mountain range.
A stone building with multiple windows and a well-lit entrance.

Le Lappe

Le Lappe
Cavriglia
NT$13,673
NT$15,112 total
includes taxes & fees
Oct 13 - Oct 14
Le Lappe
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 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.

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
NT$2,322
NT$2,697 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
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.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
NT$4,853
NT$5,624 total
includes taxes & fees
Oct 25 - Oct 26
Castello di Tornano Wine Resort
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 bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
NT$2,898
NT$3,473 total
includes taxes & fees
Oct 22 - Oct 23
Ultimo Mulino Wellness Country Hotel
A stone building with arched windows, a grassy courtyard, and outdoor seating.
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.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
NT$11,095
NT$12,491 total
includes taxes & fees
Oct 22 - Oct 23
Pieve Aldina - Relais & Châteaux
Save an average of 15% on thousands of hotels when you're signed in

Top Montegrossi Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here again."
Ralph 2-night trip
Posted 17 hours ago
Hotel Italia
Il Chiostro del Carmine

Il Chiostro del Carmine

10/10 Excellent
"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."
Katharine 3-night trip
Posted 20 hours ago
Il Chiostro del Carmine
Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Beautiful hotel in the city center with free parking which can be difficult to find. The staff was terrific"
Mark 3-night trip
Posted 1 day ago
Palazzo Ravizza
Hotel Athena

Hotel Athena

10/10 Excellent
"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"
Hillaine 3-night trip
Posted 2 days ago
Hotel Athena
Fattoria di Vegi

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!"
Lauren 1-night trip
Posted 4 days ago
Fattoria di Vegi
Grand Hotel Continental Siena – Starhotels Collezione

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."
JOHN 3-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Four Points by Sheraton Siena

Four Points by Sheraton Siena

8/10 Good
"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."
Rajendra 3-night trip
Posted 6 days ago
Four Points by Sheraton Siena
Castello di Spaltenna- Small Luxury Hotels of the World

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."
Sonja 3-night trip
Posted 9 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Toscana Ambassador

Hotel Toscana Ambassador

8/10 Good
"Close to train station"
Marian 1-night trip
Posted 10 days ago
Hotel Toscana Ambassador

More cheap stays in Montegrossi

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
NT$1,829
NT$2,119 total
Nov 5 - Nov 6
includes taxes & fees
7.8/10 Good! (259 reviews)
Cannon d'Oro
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
NT$2,465
NT$2,818 total
Nov 4 - Nov 5
includes taxes & fees
10/10 Exceptional! (50 reviews)
Torre del Fuggisole
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
NT$2,692
NT$3,068 total
Nov 4 - Nov 5
includes taxes & fees
7.8/10 Good! (451 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
NT$3,028
NT$3,438 total
Nov 3 - Nov 4
includes taxes & fees
8.8/10 Excellent! (111 reviews)
Albergo Centrale
Castello di Bossi

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI
NT$2,293
NT$5,491 total
Oct 19 - Oct 20
includes taxes & fees
Castello di Bossi
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

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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