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Montegrossi Vacation Rentals

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Montegrossi vacation 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
$150 nightly
The price is $175
Aug 3 - Aug 4
Total with taxes and fees
L' Eroico
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (37 reviews)
"Great spot"
Canada
Philippe
$172 nightly
The price is $190
Aug 10 - Aug 11
Total with taxes and fees
Villa di Sotto
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

3. Borgo di Erboli

Borgo di Erboli
Cavriglia
$118 nightly
The price is $132
Sep 1 - Sep 2
Total with taxes and fees
Borgo di Erboli
Exterior

4. 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
$183 nightly
The price is $211
Aug 4 - Aug 5
Total with taxes and fees
Borgo Argenina
Aerial view

5. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
$161 nightly
The price is $186
Aug 9 - Aug 10
Total with taxes and fees
Villa Curina Resort
Free daily buffet breakfast

6. 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
$302 nightly
The price is $336
Aug 6 - Aug 7
Total with taxes and fees
Terre di Baccio
Exterior

7. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (328 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
$87 nightly
The price is $99
Aug 6 - Aug 7
Total with taxes and fees
Hu Norcenni Girasole Village
Aerial view

8. 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
$228 nightly
The price is $253
Aug 31 - Sep 1
Total with taxes and fees
Riserva di Fizzano Residence
View from room

9. 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
$84 nightly
The price is $95
Aug 9 - Aug 10
Total with taxes and fees
Chianti Village Morrocco
Property grounds

10. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (45 reviews)
"Clean room, amazing staff"
Canada
Talha
$262 nightly
The price is $293
Aug 23 - Aug 24
Total with taxes and fees
Ca' Bianca Tuscany Relais
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
$82 nightly
The price is $95
Aug 3 - Aug 4
Total with taxes and fees
Mariani Bed & Breakfast
Front of property

12. 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
$177 nightly
The price is $195
Sep 2 - Sep 3
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
Outdoor pool

13. 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
$151 nightly
The price is $171
Aug 9 - Aug 10
Total with taxes and fees
Villa Rosa Panzano
Room amenity

14. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (469 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
$115 nightly
The price is $131
Aug 3 - Aug 4
Total with taxes and fees
Siena Vip
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

15. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (248 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
$122 nightly
The price is $139
Aug 26 - Aug 27
Total with taxes and fees
La Terrazza Sul Campo Rooming House
Lobby

16. 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
$177 nightly
The price is $194
Aug 6 - Aug 7
Total with taxes and fees
Villa Cassia di Baccano
Exterior

17. Villa Norcenni Aparthotel

Villa Norcenni Aparthotel
2.0 star property
Figline e Incisa Valdarno
7.4 out of 10, Good, (22 reviews)
"It was clean and safe."
United Kingdom
Laka
$85 nightly
The price is $97
Aug 6 - Aug 7
Total with taxes and fees
Villa Norcenni Aparthotel
Panoramic Apartment (2) | Terrace/patio

18. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 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
$133 nightly
The price is $149
Aug 18 - Aug 19
Total with taxes and fees
Casa Vacanze Squarcialupi
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

19. 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
$118 nightly
The price is $134
Aug 30 - Aug 31
Total with taxes and fees
Residenzia del Sogno
Garden view

20. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$108 nightly
The price is $125
Sep 1 - Sep 2
Total with taxes and fees
Villa San Filippo
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

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"A truly remarkable place. The staff made the stay even better. I highly recommend this hotel if you’re looking for a place in Chianti."
Kurt 4-night trip
Posted 23 hours ago
Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Montegrossi

Everything you need to know about Montegrossi vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montegrossi vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montegrossi vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montegrossi vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montegrossi. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montegrossi in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montegrossi rentals

At Expedia, we put the best Montegrossi vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montegrossi rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montegrossi vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montegrossi. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 an electric kettle. 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.