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
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Montegrossi vacation rentals

Reception

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B
Exterior

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
Bathroom

Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (155 reviews)
"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"
United States
Niels G.
Piazza Paradiso Accomodation
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (335 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Premium bedding, down comforters, pillowtop beds, minibar

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.0 out of 10, Wonderful, (26 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is P4,093
P5,393 total
includes taxes & fees
Mar 14 - Mar 15
Tuscasì Aparthotel
Exterior

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Personal people are very good. "
Switzerland
Wenjuan
The price is P4,488
P5,211 total
includes taxes & fees
Mar 22 - Mar 23
Villa le Camelie Siena
City view from property

Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very Good, (17 reviews)
"Great location. Easier if travel light if you stay in top floors. Simple but clean. Good cost-benefit balance. "
United States
Carlos
Birbo Bike Hospitality
Exterior

THE MONNA LISA RESORT

THE MONNA LISA RESORT
Arezzo
9.2 out of 10, Wonderful, (9 reviews)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
THE MONNA LISA RESORT
Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B
View from property

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is P5,609
P7,815 total
includes taxes & fees
Mar 11 - Mar 12
Antica Pieve B&B
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (194 reviews)
"Great location"
United Kingdom
Mina
B&B Il Corso
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
7.8 out of 10, Good, (16 reviews)
"To far out"
United States
Dennis
Castello di Modanella
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (40 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
Interior detail

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is P5,985
P6,857 total
includes taxes & fees
Mar 11 - Mar 12
La Coroncina Lodging
City view

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (68 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is P12,115
P14,971 total
includes taxes & fees
Apr 2 - Apr 3
Regis Condo
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (429 reviews)
"Nice place!"
United States
Pavel
The price is P5,997
P6,871 total
includes taxes & fees
Mar 11 - Mar 12
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.
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

NH Siena

NH Siena

10/10 Excellent
"I didn't use it. I only stayed one night."
Sohaila 1-night trip
Posted 9 hours ago
NH Siena

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 a coffee maker. 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 Chianti Sculpture Park. 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.