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.

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

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

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.

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

Gaiole in Chianti

Rama

Rp7.002.696

Rp7.906.748 total

includes taxes & fees

5 Oct - 6 Oct

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

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.

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

2. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.452.640

Rp4.979.417 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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.

3. Palazzo Ravizza

Siena Historical Center

XUESHENG

Rp4.435.951

Rp4.981.437 total

includes taxes & fees

24 Sept - 25 Sept

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

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.

A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

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

4. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.067.512

Rp2.335.398 total

includes taxes & fees

21 Sept - 22 Sept

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.

5. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

Rp2.411.762

Rp2.816.066 total

includes taxes & fees

30 Sept - 1 Oct

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

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

A dining area with brick ceiling arches, tables set with white tablecloths, and framed pictures on the walls.

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.

6. Hotel Chiusarelli

Siena City Centre

sharon

Rp3.326.281

Rp3.760.800 total

includes taxes & fees

30 Sept - 1 Oct

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

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

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

7. Delta Hotel

Montevarchi

weixing

Rp2.334.232

Rp2.567.655 total

includes taxes & fees

11 Sept - 12 Sept

A balcony with a table set for breakfast overlooking a historic cityscape with domed buildings and terraced houses.

A hotel room with a bed, a desk, a television, and a view of the city through large windows.

A room with blue chairs facing a window overlooking a cityscape with historic buildings.

A spacious lobby with a modern design, featuring a seating area with black leather sofas and ottomans, a reception desk, and a visible kitchen area in the background.

8. Hotel Minerva

Siena City Centre

Chia lin

Rp2.331.253

Rp2.666.837 total

includes taxes & fees

11 Sept - 12 Sept

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.

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.

9. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

Rp4.890.772

Rp5.502.118 total

includes taxes & fees

6 Oct - 7 Oct

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A building with a modern architectural style, featuring a prominent entrance with a sign that reads "FOUR POINTS."

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

10. Four Points by Sheraton Siena

Scacciapensieri

Raul

Rp3.484.675

Rp3.935.033 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

A courtyard with stone buildings, arched doorways, and potted plants.

11. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp4.296.788

Rp4.726.467 total

includes taxes & fees

29 Sept - 30 Sept

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

An outdoor patio with stone flooring, a table with chairs, and potted plants.

12. Hotel Borgo San Luigi

Monteriggioni

Raman

Rp3.168.720

Rp3.628.240 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

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

13. Villa Le Barone

Greve in Chianti

Aditi

Rp4.139.372

Rp4.675.578 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

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

14. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

Rp4.051.560

Rp4.558.607 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

15. Podere L'Aquila

Gaiole in Chianti

Rp3.001.100

Rp8.334.629 total

includes taxes & fees

10 Oct - 11 Oct

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

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.

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

16. Hotel Villa Campomaggio

Radda in Chianti

Krishna

Rp4.142.833

Rp4.680.137 total

includes taxes & fees

29 Sept - 30 Sept

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 dining area with a fireplace, wooden beams, and a tiled floor.

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

17. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

Rp1.491.091

Rp1.670.950 total

includes taxes & fees

20 Sept - 21 Sept

A pathway lined with trees and a large pot in the center.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

A bedroom with a bed, bedside lamps, a wooden table, and a balcony with a view of greenery.

18. Villa Montarioso

Montarioso

Michael

Rp1.468.730

Rp1.717.494 total

includes taxes & fees

8 Oct - 9 Oct

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A vineyard landscape with rows of grapevines and a person holding a glass.

A modern interior with a bar area, seating, and a staircase.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

19. Locanda le Piazze

Castellina in Chianti

Mark

Rp6.669.234

Rp7.458.426 total

includes taxes & fees

24 Sept - 25 Sept

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 modern hotel lobby with a curved reception desk, seating area, and a bar.

20. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.167.427

Rp2.384.251 total

includes taxes & fees

5 Oct - 6 Oct

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Top Montegrossi Hotel Reviews

Borgo Vescine

10/10 Excellent

"This place is simply perfection From the moment you check in to the moment you leave , you feel like royalty . Staff is impressive how polite , accommodating and welcoming Thank you Lorenzo at the bar ! Honestly no words besides EXCELLENT Anna /Canada !!!!"

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."

Hotel Athena

10/10 Excellent

"Clean, well located, friendly staff, wonderful views"

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!"

Dievole Wine Resort

10/10 Excellent

"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"

More cheap stays in Montegrossi

Cannon d'Oro

Via Montanini 28 Siena SI

Rp1.691.208

Rp1.962.220 total

24 Sept - 25 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

Rp2.223.078

Rp2.547.276 total

11 Sept - 12 Sept

includes taxes & fees

7.8/10 Good! (435 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

Rp2.776.069

Rp3.155.567 total

5 Oct - 6 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI

Rp3.084.447

Rp3.454.107 total

11 Oct - 12 Oct

includes taxes & fees

9/10 Wonderful! (20 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

Rp3.121.202

Rp3.535.213 total

11 Oct - 12 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Frequently asked questions

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 Grand Hotel Continental Siena – Starhotels Collezione. See all available top hotels, or vacation rentals in Montegrossi.

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 Castello di Albola. You'll also find Castello di Radda Winery and Castle of Brolio 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.

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Book Hotels in Montegrossi on Expedia.it

Find hotels in Montegrossi from Rp1.332.496

Change your mind

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. Tenuta CorteDomina

3. Palazzo Ravizza

4. Moody smart & comfy Hotel

5. La Certosa di Pontignano

6. Hotel Chiusarelli

7. Delta Hotel

8. Hotel Minerva

9. Chapter Chianti, a Member of Design Hotels

10. Four Points by Sheraton Siena

11. Castello Vicchiomaggio

12. Hotel Borgo San Luigi

13. Villa Le Barone

14. Villa Scacciapensieri Boutique Hotel

15. Podere L'Aquila

16. Hotel Villa Campomaggio

17. Hotel Tenuta Il Burchio

18. Villa Montarioso

19. Locanda le Piazze

20. Hotel Valdarno

Top Montegrossi Hotel Reviews

Borgo Vescine

Villa Pitiana

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Chiusarelli

Hotel Athena

Borgo San Felice Resort

Fattoria di Vegi

Dievole Wine Resort

More cheap stays in Montegrossi

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Antico Borgo Poggiarello

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

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