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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Montegrossi holiday rentals

A stone building with a yellow sign reading "b&b erioico".

1. 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 ฿5,135
฿5,954 total
includes taxes & fees
18 Oct - 19 Oct
L' Eroico
A pool area with a water slide and a stage for performances.

2. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (24 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is ฿2,121
฿2,391 total
includes taxes & fees
30 Sept - 1 Oct
Villa Norcenni Aparthotel
A stone building with a garden in front.

3. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is ฿8,019
฿9,127 total
includes taxes & fees
1 Oct - 2 Oct
Borgo Argenina
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

4. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is ฿5,245
฿7,298 total
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

5. 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 ฿2,970
฿3,420 total
includes taxes & fees
7 Oct - 8 Oct
Mariani Bed & Breakfast
A villa with a swimming pool, outdoor seating, and a tennis court.

6. 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 ฿5,663
฿6,382 total
includes taxes & fees
4 Oct - 5 Oct
Villa Curina Resort
A table with breakfast items and a view of rolling hills.

7. 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 ฿2,450
฿2,772 total
includes taxes & fees
12 Oct - 13 Oct
Chianti Village Morrocco
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

8. 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 ฿5,523
฿6,076 total
includes taxes & fees
30 Sept - 1 Oct
Relais Villa Belpoggio - Residenza d'Epoca
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

9. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is ฿4,168
฿4,738 total
includes taxes & fees
4 Oct - 5 Oct
Villa Rosa Panzano
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

10. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ฿4,290
฿4,872 total
includes taxes & fees
7 Oct - 8 Oct
Residenzia del Sogno
A pool area with a water slide and a stage for performances.

11. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
The price is ฿2,121
฿2,391 total
includes taxes & fees
30 Sept - 1 Oct
Hu Norcenni Girasole Village
A cozy living room with a stone wall, a wine rack, and two sofas.

12. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,346
฿6,310 total
includes taxes & fees
10 Oct - 11 Oct
Villa Cassia di Baccano
A rustic stone building with a courtyard.

13. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ฿3,630
฿4,146 total
includes taxes & fees
30 Sept - 1 Oct
Fullino Nero
A table with two wine glasses, a bottle, and a book.

14. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is ฿2,258
฿2,637 total
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

15. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 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 ฿4,277
฿4,934 total
includes taxes & fees
18 Oct - 19 Oct
Casa Vacanze Squarcialupi
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

16. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is ฿2,939
฿3,386 total
includes taxes & fees
30 Sept - 1 Oct
Villa Fontis Rapolano
A market with a sign reading "BAR IL POGGETTO MARKET".

17. Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (79 reviews)
"Nice property, very reasonable price"
United States
Alex
The price is ฿1,969
฿2,281 total
includes taxes & fees
1 Oct - 2 Oct
Camping Village Il Poggetto.
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.

18. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ฿2,411
฿3,149 total
includes taxes & fees
25 Oct - 26 Oct
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.
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Top Montegrossi Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"good to stay"
Jinhee 1-night trip
Posted 8 hours ago
La Certosa di Pontignano

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:

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

Frequently asked questions

Can I find a holiday rental in Montegrossi?

Yes, there are holiday rentals close to the most popular sights in Montegrossi, or you can select a more secluded option if you're looking for a relaxing stay.

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.

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 wider area.

What’s a holiday rental in Montegrossi like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montegrossi. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for small groups.