Montegrossi Holiday Rentals, Gaiole in Chianti: Private House Rentals

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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.

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

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

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

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

Gaiole in Chianti

Rama

8.698.208 ₫

9.863.226 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

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

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.

2. Tenuta CorteDomina

Radda in Chianti

Dustin

6.792.245 ₫

7.589.596 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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.

3. Delta Hotel

Montevarchi

weixing

3.382.699 ₫

3.720.969 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

A modern hotel room with a large bed, a desk, and a chair. There is a painting on the wall and a lamp on the side table.

A balcony with two chairs and a table, overlooking a building with a tiled roof and shutters.

A hotel with a sign reading "HOTEL RISTORANTE CHIUSARELLI," surrounded by greenery and a brick wall.

4. Hotel Chiusarelli

Siena City Centre

Scott

3.307.528 ₫

3.785.938 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A stone building with a window and a light fixture.

5. Agriturismo San Sano

Gaiole in Chianti

Glen

1.920.837 ₫

2.231.267 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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.

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

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

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

6. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

2.544.273 ₫

3.034.953 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

A courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

A bar area with a counter, bottles, and glasses.

7. Palazzo Ravizza

Siena Historical Center

Sherri

4.276.698 ₫

4.852.025 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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 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.

8. Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

3.723.733 ₫

4.332.358 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.

A bedroom with a large bed, a bedside table, and a chair.

A pool area with a view of a hilly landscape.

9. Borgo Del Cabreo

Greve in Chianti

Brian

6.778.001 ₫

7.574.147 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

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

10. Hotel Villa Campomaggio

Radda in Chianti

Dario

4.852.188 ₫

5.514.926 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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.

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

11. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

3.172.253 ₫

3.548.542 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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

A reception area with a wooden ceiling, a reception desk, and seating.

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.

12. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

7.087.560 ₫

7.973.505 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A clear swimming pool with a view of a lush green landscape and distant hills.

A restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.

A garden with pink roses, a lawn, and a white umbrella.

A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

13. Villa Le Barone

Greve in Chianti

Tereza

6.361.749 ₫

7.175.442 ₫ total

includes taxes & fees

17 Oct - 18 Oct

A pool with a view of a lush valley and distant buildings.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

14. Castello Vicchiomaggio

Greve in Chianti

Maryse

4.472.881 ₫

4.920.169 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

A hotel entrance with a view of historic buildings and a clear sky.

A bedroom with a large window, a bed, a nightstand, and a mirror.

A room with a white desk, chair, and a large mirror. There is a painting of a horse on the wall and a window with curtains.

15. Villa del Sole Siena

Siena City Centre

John

5.353.088 ₫

6.036.241 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

16. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

2.649.566 ₫

3.003.058 ₫ total

includes taxes & fees

26 Oct - 27 Oct

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

17. Villa San Lucchese

Poggibonsi

James

2.740.469 ₫

3.191.704 ₫ total

includes taxes & fees

30 Oct - 31 Oct

An outdoor patio area with a brick archway, potted plants, and wicker furniture.

An outdoor courtyard with stone walls, potted plants, and a wooden door leading to an interior space.

A room with a large window, a radiator, and a television on a stand.

A swimming pool with steps leading into it, surrounded by lounge chairs and a stone wall with greenery.

18. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

2.152.015 ₫

2.411.596 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

A swimming pool surrounded by lush greenery and a stone pathway.

A large, historic building with a covered patio and a well-maintained garden.

19. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

5.001.562 ₫

5.649.376 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A table set for breakfast with a scenic view of hills and a cloudy sky.

A breakfast buffet with various food items and beverages, set in a room with arched ceilings and yellow walls.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

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

20. Palazzo di Valli

Siena

Payton

3.994.179 ₫

4.541.530 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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Top Montegrossi Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"10/10 - we loved every bit of our stay at Fattoria di Vegi. The hotel is beautiful with great views across the Tuscan hills, an amazing pool, the rooms and decor are wonderful and we also loved the food at the restaurant. We would highly recommend this hotel to anybody visiting the area and will definitely be coming back."

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."

Borgo Scopeto Wine & Country Relais

8/10 Good

"Staff are nice!"

Four Points by Sheraton Siena

10/10 Excellent

"Excellent property. It was well maintained, and the staff was friendly. I would definitely stay here again."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."

Hotel Chiusarelli

10/10 Excellent

"Really enjoyed our stay. Room was spacious and clean. Very nice breakfast and the staff were very kind and helpful."

La Certosa di Pontignano

10/10 Excellent

"Everything about this property is wonderful from the lodging to the staff!"

Hotel Athena

10/10 Excellent

"Excellent location with free. And easy parking. Great breakfast, extremely kind and helpful staff, small but adequate shower. Would definitely stay here in the future!!"

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"Beautiful hotel that is close to a bus line to get into the city. The views and accommodations make this a wonderful place to stay."

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

1.510.133 ₫

1.808.803 ₫ total

25 Oct - 26 Oct

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

2.904.858 ₫

3.343.276 ₫ total

30 Sept - 1 Oct

includes taxes & fees

7.8/10 Good! (442 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

3.796.922 ₫

4.324.271 ₫ total

22 Oct - 23 Oct

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

3.933.662 ₫

4.474.961 ₫ total

30 Sept - 1 Oct

includes taxes & fees

10/10 Exceptional! (50 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

1.897.366 ₫

4.542.783 ₫ total

20 Oct - 21 Oct

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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Hotels in Montegrossi with star rating

Frequently asked questions

What's the seasonal weather like in Montegrossi?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montegrossi is 946 mm.

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Book Hotels in Montegrossi on Expedia.it

Find hotels in Montegrossi from 1.808.803 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

Star rating

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Our top choices for Montegrossi hotels

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

2. Tenuta CorteDomina

3. Delta Hotel

4. Hotel Chiusarelli

5. Agriturismo San Sano

6. La Certosa di Pontignano

7. Palazzo Ravizza

8. Castello di Tornano Wine Resort

9. Borgo Del Cabreo

10. Hotel Villa Campomaggio

11. Villa Casagrande Resort & SPA

12. Chapter Chianti, a Member of Design Hotels

13. Villa Le Barone

14. Castello Vicchiomaggio

15. Villa del Sole Siena

16. Hotel Colle Etrusco Salivolpi

17. Villa San Lucchese

18. Hotel Tenuta Il Burchio

19. Villa Scacciapensieri Boutique Hotel

20. Palazzo di Valli

Top Montegrossi Hotel Reviews

Fattoria di Vegi

Hotel Minerva

Borgo Scopeto Wine & Country Relais

Four Points by Sheraton Siena

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

La Certosa di Pontignano

Hotel Athena

Villa Ermellina Siena, a Tribute Portfolio Hotel

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Castello di Bossi

Porta Pispini Residence

Hotels in Montegrossi with star rating

Frequently asked questions

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