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Montegrossi Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montegrossi vacation 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 NT$4,336
NT$5,056 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is NT$5,348
NT$5,883 total
includes taxes & fees
Oct 12 - Oct 13
Villa di Sotto
A stone building with a garden in front.

3. 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 NT$5,435
NT$6,265 total
includes taxes & fees
Oct 15 - Oct 16
Borgo Argenina
A villa with a swimming pool, outdoor seating, and a tennis court.

4. 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 NT$3,869
NT$4,399 total
includes taxes & fees
Oct 18 - Oct 19
Villa Curina Resort
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 NT$5,169
NT$5,686 total
includes taxes & fees
Oct 13 - Oct 14
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.

6. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (57 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is NT$4,291
NT$4,863 total
includes taxes & fees
Oct 12 - Oct 13
Villa Rosa Panzano
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

7. 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 NT$8,660
NT$9,669 total
includes taxes & fees
Oct 30 - Oct 31
Terre di Baccio
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

8. 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 NT$5,071
NT$5,722 total
includes taxes & fees
Oct 12 - Oct 13
Residenzia del Sogno
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

9. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
Ca' Bianca Tuscany Relais
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

10. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NT$6,225
NT$6,919 total
includes taxes & fees
Oct 19 - Oct 20
Riserva di Fizzano Residence
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. 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 NT$3,502
NT$4,067 total
includes taxes & fees
Nov 11 - Nov 12
Casa Vacanze Squarcialupi
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

12. 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 NT$2,779
NT$3,200 total
includes taxes & fees
Oct 14 - Oct 15
Mariani Bed & Breakfast
A cozy living room with a stone wall, a wine rack, and two sofas.

13. 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 NT$3,951
NT$4,347 total
includes taxes & fees
Oct 21 - Oct 22
Villa Cassia di Baccano
A stone building with multiple windows and a chimney.

14. 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 NT$4,092
NT$4,644 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

15. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (47 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 NT$7,721
NT$8,636 total
includes taxes & fees
Oct 12 - Oct 13
Castello di Gargonza
A table with breakfast items and a view of rolling hills.

16. 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 NT$2,696
NT$3,038 total
includes taxes & fees
Oct 18 - Oct 19
Chianti Village Morrocco
A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

17. Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.8 out of 10, Exceptional, (7 reviews)
"Very nice hotel with friendly stad"
Denmark
Lisette
The price is NT$3,657
NT$4,130 total
includes taxes & fees
Oct 12 - Oct 13
Casa Vacanze Le Fornaci
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Greatly enjoyed the front desk staff."
Dreslaine 2-night trip
Posted 1 hour ago
Palazzo Ravizza

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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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.