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Montegrossi Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Montegrossi vacation rentals

A stone building with a garden in front.

1. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is AED 652
AED 750 total
includes taxes & fees
26 Oct - 27 Oct
Borgo Argenina
A villa with a swimming pool, outdoor seating, and a tennis court.

2. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AED 544
AED 615 total
includes taxes & fees
21 Oct - 22 Oct
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is AED 617
AED 679 total
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A stone building with a yellow sign reading "b&b erioico".

4. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is AED 474
AED 555 total
includes taxes & fees
12 Nov - 13 Nov
L' Eroico
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

5. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is AED 513
AED 564 total
includes taxes & fees
19 Nov - 20 Nov
Relais Villa Belpoggio - Residenza d'Epoca
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

6. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is AED 487
AED 552 total
includes taxes & fees
30 Oct - 31 Oct
Residenzia del Sogno
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

7. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is AED 334
AED 384 total
includes taxes & fees
29 Oct - 30 Oct
Mariani Bed & Breakfast
A stone building with multiple windows and a chimney.

8. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AED 471
AED 535 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

9. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is AED 425
AED 492 total
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Squarcialupi
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (27 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is AED 333
AED 654 total
includes taxes & fees
21 Oct - 22 Oct
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A cozy living room with a stone wall, a wine rack, and two sofas.

11. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AED 423
AED 466 total
includes taxes & fees
21 Oct - 22 Oct
Villa Cassia di Baccano
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

12. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is AED 355
AED 397 total
includes taxes & fees
2 Nov - 3 Nov
Relais Villa Belvedere
A table with breakfast items and a view of rolling hills.

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is AED 313
AED 352 total
includes taxes & fees
21 Oct - 22 Oct
Chianti Village Morrocco
A rustic stone building with a courtyard.

14. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (57 reviews)
"Very nice place close to"
Canada
Annie
The price is AED 373
AED 427 total
includes taxes & fees
2 Nov - 3 Nov
Fullino Nero
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

15. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is AED 1,085
AED 1,210 total
includes taxes & fees
6 Nov - 7 Nov
Terre di Baccio
An arched stone bridge with a white building on the right, featuring a balcony with plants.

16. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is AED 398
AED 437 total
includes taxes & fees
26 Oct - 27 Oct
Locanda Antico Borgo
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is AED 889
AED 995 total
includes taxes & fees
21 Oct - 22 Oct
Castello di Gargonza
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

18. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (355 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is AED 230
AED 270 total
includes taxes & fees
5 Nov - 6 Nov
ApartHotel Anghel
A table set with various items including a book, glassware, and decorative objects against a stone wall backdrop.

19. 'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning

'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
Gaiole in Chianti
9.8 out of 10, Exceptional, (7 reviews)
"Georgeous clean home in home in an idyllic town! We had a fantastic stay here. I would very happily return."
Germany
Mariah M.
The price is AED 1,329
AED 1,470 total
includes taxes & fees
31 Oct - 1 Nov
'La Casa Di Emma' Apartment with Wi-Fi and Air Conditioning
A bedroom with a bed, bedside table, and a window with a view of greenery.

20. La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is AED 387
AED 442 total
includes taxes & fees
10 Nov - 11 Nov
La Coroncina Lodging
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montegrossi Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Great location amazing place"
Rodolfo 1-night trip
Posted 1 hour ago
La Certosa di Pontignano

Frequently asked questions

Can I find a vacation rental in Montegrossi?

Yes, there are vacation rentals close to well known sights in Montegrossi, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals 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.

What’s there to see and do in Montegrossi?

Explore the area and family-friendly sights such as Borgo di Vescine - Tenute di Castelvecchi, or get out into nature at a spot like Terme Antica Querciolaia. Badia a Coltibuono and Meleto Castle are a couple of places you'll find in the larger area.

What’s a vacation rental in Montegrossi like?

Vacation rentals are private properties you can stay in for short or long periods in Montegrossi. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.