Montalcino Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Montalcino

Our top choices for Montalcino holiday rentals

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Pool

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (62)
"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (90)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (83)
"The villa is huge and well appointed with anything you could imagine There are two large dining rooms inside and several well appointed outside patio areas. The bucolic setting includes birds , roaming sheep down the hill meandering from field to field. Couldn’t be more restful! Also close enough to Siena , San gimingnano Assisi for day trips and even Florence Will definitely return. "
Villa in Montalcino, exclusive for you, stunning view!!!
The House of Alice, charm and relaxation
Exterior detail

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (62)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
The price is HK$1,645
HK$2,147 total
includes taxes & fees
9 Sept - 10 Sept
The House of Alice, charm and relaxation
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Outdoor pool

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

10.0 out of 10, Exceptional, (54)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!
Corte Francigena
Private kitchen

Corte Francigena

9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
The price is HK$1,236
HK$1,470 total
includes taxes & fees
29 Sept - 30 Sept
Corte Francigena
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Outdoor pool

Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

10.0 out of 10, Exceptional, (12)
"Great for a group!"
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Antico Brunello
Outdoor pool

Antico Brunello

The price is HK$59,978
HK$66,067 total
includes taxes & fees
17 Sept - 18 Sept
Antico Brunello
Casanova - Panoramic Rooms and Suites
Front of property – evening/night

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (66)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
The price is HK$1,416
HK$1,593 total
includes taxes & fees
9 Sept - 10 Sept
Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Breakfast, lunch, dinner served; local cuisine

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (125)
"Such friendly staff, loved Pienza and the property was such a good location! "
Hotel San Gregorio
Residenza d'Epoca Palazzo Borghesi
View from room

Residenza d'Epoca Palazzo Borghesi

9.6 out of 10, Exceptional, (110)
"Beautiful, unique property in central Siena. Sonia at reception was excellent! "
The price is HK$2,276
HK$2,540 total
includes taxes & fees
16 Sept - 17 Sept
Residenza d'Epoca Palazzo Borghesi
ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.4 out of 10, Very good, (324)
"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."
The price is HK$905
HK$1,032 total
includes taxes & fees
10 Sept - 11 Sept
ApartHotel Anghel
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (71)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool
Country house, really private pool A.C. 20 mn beaches facing Elba Island
Outdoor pool

Country house, really private pool A.C. 20 mn beaches facing Elba Island

7.6 out of 10, Good, (9)
"L'annonce ne correspond pas à la réalité !!!"
Country house, really private pool A.C. 20 mn beaches facing Elba Island
Camping Siena Colleverde
Exterior

Camping Siena Colleverde

3.0 star property
8.2 out of 10, Very good, (154)
"Safe, great proximity to Siena without being too close, nice pool."
Camping Siena Colleverde
Bosco della Spina
Aerial view

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
Tuscasì Aparthotel
View from room

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (20)
"Limited option of restaurant around the area, the view in the morning is serene, breakfast was good but limited choice."
The price is HK$630
HK$720 total
includes taxes & fees
25 Sept - 26 Sept
Tuscasì Aparthotel
Borgo Argiano
Terrace/patio

Borgo Argiano

10.0 out of 10, Exceptional, (68)
"Very comfortable stay. "
Borgo Argiano
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Il Battistero Siena - Residenza d'Epoca
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (176)
"Excellent staffing, nice facility and great location"
The price is HK$1,325
HK$1,495 total
includes taxes & fees
24 Sept - 25 Sept
Il Battistero Siena - Residenza d'Epoca
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montalcino Hotel Reviews

Find out more about Montalcino

Find out more about Montalcino

Search for holiday rentals in Montalcino on Expedia! You can easily find your home rentals, villas, holiday apartments in Montalcino using one of the methods below:

  • View our selection of featured holiday rentals in Montalcino
  • Use the map to find apartments and other holiday homes in the Montalcino neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montalcino while they last

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

Frequently asked questions

Are there holiday rentals in Montalcino?

Yes, there are holiday rentals in Montalcino close to Bosco della Ragnaia, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Montalcino is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What are some of the best holiday rentals that Montalcino has to offer?

Borgo Argiano: This holiday home rental outside of Montalcino 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. Another good choice for your trip to Montalcino is The House of Alice, charm and relaxation.

How many holiday rentals are there in Montalcino?

With 39 Expedia holiday rentals, you're guaranteed to find just the right place for your Montalcino stay.

What’s there to see and do in Montalcino?

Enjoy the outdoors at Val di Chiana and Val di Merse, or simply take in cultural attractions like Museum of Brunello and Civic and Diocesan Museum of Sacred Art of Montalcino. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a holiday rental in Montalcino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montalcino. Holiday rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.