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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Montegrossi holiday rentals

Exterior

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 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 ฿5,425
฿6,274 total
includes taxes & fees
12 Sept - 13 Sept
L' Eroico
Exterior

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is ฿8,677
฿9,851 total
includes taxes & fees
23 Aug - 24 Aug
Borgo Argenina
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

3. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is ฿4,267
฿4,770 total
includes taxes & fees
27 Aug - 28 Aug
Borgo di Erboli
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

4. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
The price is ฿5,308
฿5,839 total
includes taxes & fees
10 Sept - 11 Sept
Villa di Sotto
Free daily buffet breakfast

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is ฿10,448
฿11,646 total
includes taxes & fees
17 Aug - 18 Aug
Terre di Baccio
Aerial view

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is ฿6,275
฿7,056 total
includes taxes & fees
23 Aug - 24 Aug
Villa Curina Resort
Exterior

7. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (329 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is ฿3,428
฿3,885 total
includes taxes & fees
16 Aug - 17 Aug
Hu Norcenni Girasole Village
Front of property

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 ฿5,892
฿6,481 total
includes taxes & fees
2 Sept - 3 Sept
Relais Villa Belpoggio - Residenza d'Epoca
Property grounds

9. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is ฿9,450
฿10,549 total
includes taxes & fees
17 Aug - 18 Aug
Ca' Bianca Tuscany Relais
Aerial view

10. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿6,640
฿7,380 total
includes taxes & fees
8 Sept - 9 Sept
Riserva di Fizzano Residence
Lounge

11. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ฿3,238
฿3,715 total
includes taxes & fees
18 Aug - 19 Aug
Mariani Bed & Breakfast
Lobby

12. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (24 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿6,624
฿7,286 total
includes taxes & fees
15 Sept - 16 Sept
Villa Cassia di Baccano
View from room

13. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ฿3,186
฿3,581 total
includes taxes & fees
15 Sept - 16 Sept
Chianti Village Morrocco
8 outdoor pools

14. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
Villa Marcolina
Exterior

15. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (23 reviews)
"It was clean and safe."
United Kingdom
Laka
The price is ฿3,420
฿3,877 total
includes taxes & fees
16 Aug - 17 Aug
Villa Norcenni Aparthotel
Garden view

16. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (47 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ฿3,616
฿4,208 total
includes taxes & fees
12 Sept - 13 Sept
Villa San Filippo
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

17. 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 ฿4,069
฿4,630 total
includes taxes & fees
28 Aug - 29 Aug
Residenzia del Sogno
Room amenity

18. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (474 reviews)
"Lovely, clean room, comfy bed, decent breakfast "
United Kingdom
Andrew
The price is ฿4,184
฿4,756 total
includes taxes & fees
18 Aug - 19 Aug
Siena Vip
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

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"
C 3-night trip
Posted 22 hours ago
Villa Casagrande Resort & SPA

Find out more about Montegrossi

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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 an espresso maker. 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 Chianti Sculpture Park. 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.