Montegrossi Holiday Rentals, Gaiole in Chianti: Private House Rentals

Q: What are some of the best holiday rentals that Montegrossi has to offer?

Borgo Argiano : This holiday home rental outside of Montegrossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library. See all vacation rentals in Montegrossi .

Q: 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 on-site pool. View all hotels with pools in Montegrossi .

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Our top choices for Montegrossi hotels

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

1. Hotel Valdarno

Montevarchi

Emmanuel

฿4,379 total

includes taxes & fees

23 Nov - 24 Nov

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

2. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

฿2,903 total

includes taxes & fees

9 Dec - 10 Dec

A spa area with white massage chairs arranged in a row under a brick archway.

3. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

฿4,128 total

includes taxes & fees

8 Dec - 9 Dec

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

4. Dievole Wine Resort

Castelnuovo Berardenga

Magdalena

฿10,640 total

includes taxes & fees

16 Nov - 17 Nov

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

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

฿14,221 total

includes taxes & fees

14 Nov - 15 Nov

A stone-walled interior with a staircase, wooden doors, and a patterned rug.

6. Tenuta CorteDomina

Radda in Chianti

piyanut

฿8,789 total

includes taxes & fees

14 Nov - 15 Nov

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

7. Delta Hotel

Montevarchi

weixing

฿4,716 total

includes taxes & fees

16 Nov - 17 Nov

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

8. Borgo Vescine

Radda in Chianti

Natalie

฿17,275 total

includes taxes & fees

14 Nov - 15 Nov

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

9. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

฿4,253 total

includes taxes & fees

20 Nov - 21 Nov

A buffet with various food items and utensils.

10. Hotel Il Viandante

Terranuova Bracciolini

jessica

฿4,104 total

includes taxes & fees

13 Dec - 14 Dec

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

11. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Rodolfo

฿2,859 total

includes taxes & fees

16 Nov - 17 Nov

A courtyard with stone flooring, arched walkways, and a central fountain.

12. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

฿3,501 total

includes taxes & fees

13 Dec - 14 Dec

An aerial view of a large estate with a swimming pool, tennis courts, and a vineyard.

13. The Club House

Castelnuovo Berardenga

Natalyn

฿17,136 total

includes taxes & fees

22 Nov - 23 Nov

A large building with a swimming pool, outdoor seating, and a view of surrounding hills.

14. Palagina la Dimora

Figline e Incisa Valdarno

Danielle

฿4,150 total

includes taxes & fees

14 Nov - 15 Nov

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.

15. Belvedere di San Leonino

Castellina in Chianti

Kevork

฿4,169 total

includes taxes & fees

21 Nov - 22 Nov

A stone building with wooden shutters, a bench, and hanging purple flowers.

16. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

฿5,625 total

includes taxes & fees

16 Nov - 17 Nov

A rustic stone interior with a dining area, two armchairs, a table with a lamp, and a view through an arched doorway.

17. Castello di Volpaia

Radda in Chianti

Stenley

฿7,818 total

includes taxes & fees

5 Dec - 6 Dec

A stone-walled room with tables set for dining, a staircase, and a lamp.

18. Albergo Il Colombaio

Castellina in Chianti

Christine

฿5,726 total

includes taxes & fees

17 Nov - 18 Nov

A modern lobby with a bar area, seating, and a large window.

19. Hotel Toscana

Figline e Incisa Valdarno

Anonymous traveller

฿4,749 total

includes taxes & fees

16 Nov - 17 Nov

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

20. Sangallo Park Hotel

Vico Alto

Marcio Tadeu

฿4,023 total

includes taxes & fees

22 Nov - 23 Nov

View all properties

Top Montegrossi Hotel Reviews

Hotel Palazzo San niccolò & Spa

Radda in Chianti

10/10 Excellent

Ulrika

Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

10/10 Excellent

Anonymous traveller

La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

10/10 Excellent

This place is surreal. We felt like we were on the set of the Name of the Rose. Sleeping in a real XIV century monastery, with its own church (with amazing frescoes), on a hill overlooking the grapes and olive trees dotted countryside...just unbelievable. We stay in one the celle, which is a 3 bedroom apartment on 2 floors, with your own private garden...yes, that's correct. Simply unheard of. The location is great too (Siena is a short drive away). The only setbacks were breakfast, very...

Ivo

Hotel Il Viandante

Terranuova Bracciolini

10/10 Excellent

James

Belvedere di San Leonino

Castellina in Chianti

10/10 Excellent

Jess

Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

10/10 Excellent

Natasha

Castello di Volpaia

Radda in Chianti

10/10 Excellent

Tomi

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Excellent

Yoke yin

A modern bedroom with a wooden headboard, a large bed with white linens, a bedside table with a lamp, and a sliding glass door leading to an outdoor patio with a table and chairs.

Hotel Ristorante La Dama nella Vigna

Monteriggioni

10/10 Excellent

Ryan

Castello di Fonterutoli Wine Resort

Castellina in Chianti

10/10 Excellent

Claire

Palagina la Dimora

Figline e Incisa Valdarno

10/10 Excellent

Auste

A stone building with outdoor seating and a pool in the background.

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Excellent

My husband and I had a wonderful stay at Poggio del Drago - Emanuele is a perfect host and made us feel very welcome throughout our stay. The room itself was lovely - recently renovated and looking lovely. The pool is perfectly located, overlooking the olive groves and with plenty of loungers for all guests. Breakfast was great - a large breakfast table where all guests sat together and took breakfast - an array of sliced meats, cereals, and also a coffee machine to make yourself a cappuccino or...

katy

The Club House

Castelnuovo Berardenga

10/10 Excellent

A wonderful stay at The Club House. This is a gorgeous place in a beautiful setting in the heart of Chianti. The property is immaculate, the staff friendly and the food delicious. We have been to wonderful hotels all over the world but this place is really special. It was our second visit (we stayed in August 2025). Everything was great but if I had to be picky I would say the gym is insanely hot in the morning (despite asking for the air con to be put on the evening before). Also, having...

Elizabeth

Frequently Asked Questions

What are some of the best holiday rentals that Montegrossi has to offer?

Borgo Argiano: This holiday home rental outside of Montegrossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday 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 reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montegrossi.

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 on-site pool. View all hotels with pools in Montegrossi.

How is it to stay in Montegrossi?

Visitors to Montegrossi will definitely find plenty to explore and enjoy. In Montegrossi, there are 4 hotels and other accommodation options 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. Take a look at what more there is 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 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.

Where is the best place to 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 traveller data. Two other options for your visit to the area are Hotel Athena and Hotel Executive. See all available top hotels, or vacation rentals in Montegrossi.

Find hotels in Montegrossi from ฿2,327

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montegrossi

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Montegrossi hotels

1. Hotel Valdarno

2. Hotel Palazzo San niccolò & Spa

3. Palazzo Leopoldo Dimora Storica & Spa

4. Dievole Wine Resort

5. Chapter Chianti, a Member of Design Hotels

6. Tenuta CorteDomina

7. Delta Hotel

8. Borgo Vescine

9. Moody smart & comfy Hotel

10. Hotel Il Viandante

11. La Certosa di Pontignano - Place of Charme

12. Villa Casagrande Resort & SPA

13. The Club House

14. Palagina la Dimora

15. Belvedere di San Leonino

16. Castello di Fonterutoli Wine Resort

17. Castello di Volpaia

18. Albergo Il Colombaio

19. Hotel Toscana

20. Sangallo Park Hotel

Top Montegrossi Hotel Reviews

Hotel Palazzo San niccolò & Spa

10/10 Excellent

Frequently Asked Questions

What are some of the best holiday rentals that Montegrossi has to offer?

If I need to cancel my hotel reservation in Montegrossi, will I receive a refund?

What are some hotels with pools in Montegrossi?

How is it to stay in Montegrossi?

What are the top places to visit in Montegrossi?

What's the seasonal weather like in Montegrossi?

Where is the best place to stay in Montegrossi?