Default HTG hotel image

Montegrossi Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 P11,321
P13,023 total
includes taxes & fees
Oct 31 - Nov 1
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, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is P9,304
P10,519 total
includes taxes & fees
Oct 26 - Oct 27
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 P11,302
P12,432 total
includes taxes & fees
Oct 29 - Oct 30
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 P8,207
P9,597 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (81 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 P17,254
P19,264 total
includes taxes & fees
Nov 6 - Nov 7
Terre di Baccio
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

6. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is P10,298
P11,328 total
includes taxes & fees
Oct 26 - Oct 27
Relais Villa Belpoggio - Residenza d'Epoca
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. 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 P8,420
P9,547 total
includes taxes & fees
Oct 30 - Oct 31
Residenzia del Sogno
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

8. 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 P7,694
P8,891 total
includes taxes & fees
Nov 6 - Nov 7
Casa Vacanze Squarcialupi
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

9. 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 P5,845
P6,715 total
includes taxes & fees
Oct 27 - Oct 28
Mariani Bed & Breakfast
A stone building with multiple windows and a chimney.

10. 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 P8,152
P9,252 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
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 P7,322
P8,054 total
includes taxes & fees
Oct 27 - Oct 28
Villa Cassia di Baccano
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

12. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (60 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is P7,876
P8,948 total
includes taxes & fees
Nov 2 - Nov 3
Guild Living Siena Senior Resort & Residence
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)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is P5,398
P6,081 total
includes taxes & fees
Oct 26 - Oct 27
Chianti Village Morrocco
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

14. 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 P15,382
P17,205 total
includes taxes & fees
Oct 26 - Oct 27
Castello di Gargonza
A spacious kitchen with a central island, wooden furniture, and pendant lighting.

15. 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 P6,901
P7,698 total
includes taxes & fees
Nov 7 - Nov 8
Relais Villa Belvedere
A table with two wine glasses, a bottle, and a book.

16. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is P5,168
P5,970 total
includes taxes & fees
Nov 12 - Nov 13
Domus il Palio B&B
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

17. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P3,953
P5,274 total
includes taxes & fees
Nov 4 - Nov 5
Tuscasì Aparthotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montegrossi Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"
William 2-night trip
Posted 14 hours ago
Hotel Chiusarelli

Find out more about Montegrossi

Search for holiday rentals in Montegrossi on Expedia! You can easily find your home rentals, villas, holiday apartments in Montegrossi using one of the methods below:

  • View our selection of featured holiday rentals in Montegrossi
  • Use the map to find apartments and other holiday homes in the Montegrossi neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montegrossi while they last

Look no further and take a look at our great range of rental properties in Montegrossi!

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.