Brunello di Montalcino Wine Area Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Brunello di Montalcino Wine Area vacation rentals

Front of property
Idolina Guest House

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House
Deluxe Condo | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
Corte Francigena

Corte Francigena

Corte Francigena
Montalcino
9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
United States
Svetlana
The price is ￥25,668
￥30,443 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Corte Francigena
Free WiFi
Affittacamere Mariuccia

Affittacamere Mariuccia

Affittacamere Mariuccia
Montalcino
9.0 out of 10, Wonderful, (11)
"The apartment was big enough, the owner very polite and helpful. But, there were bugs at our mattress... "
United Kingdom
Angeliki
Affittacamere Mariuccia
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets
B&B Le Scalette di Piazza

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza
Pool
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is ￥1,094,654
￥1,186,642 total
includes taxes & fees
Dec 27 - Dec 28
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Interior
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Il Borghetto - La Ghibellina Townhouse, private apartment with balcony
Castelnuovo dell'abate
9.0 out of 10, Wonderful, (2)
"Great location and a well maintained property"
United Kingdom
Matt D.
The price is ￥22,077
￥29,804 total
includes taxes & fees
Dec 27 - Dec 28
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony
1 bedroom, free WiFi, bed sheets
Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi

Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi

Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi
Montalcino
10.0 out of 10, Exceptional, (1)
"Host is very nice. The view is stunning. "
United States
Yufen Bebie W.
The price is ￥24,680
￥25,416 total
includes taxes & fees
Dec 29 - Dec 30
Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi
Outdoor dining
Charming apartment in the historic center with large terrace and beautiful view

Charming apartment in the historic center with large terrace and beautiful view

Charming apartment in the historic center with large terrace and beautiful view
Montalcino
8.0 out of 10, Very Good, (1)
"Appartamento vecchio stile ma molto spazioso e con tutto quello che serve, posizione ottima "
Italy
Marco R.
The price is ￥18,214
￥31,828 total
includes taxes & fees
Dec 27 - Dec 28
Charming apartment in the historic center with large terrace and beautiful view
Outdoor dining
Montalcino Tuscany Home - Apartment "C" Terrace

Montalcino Tuscany Home - Apartment "C" Terrace

Montalcino Tuscany Home - Apartment "C" Terrace
Montalcino
The price is ￥25,389
￥33,484 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Montalcino Tuscany Home - Apartment "C" Terrace
Outdoor dining
Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is ￥22,077
￥29,804 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Il Borghetto - The House of Elba, rooftop panoramic terrace
Exterior detail
The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (17)
"Very beautiful location, clean exactly represented as advertised. A little limited for local eating. We cooked dinner in. Would recommend it to others. Cheers"
United States
David & Teri B.
The price is ￥27,596
￥37,347 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Casetta di Brunello, quiet and breathtaking views
Outdoor dining
Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is ￥22,041
￥25,714 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Podere Belsogno-camera Lavanda
Pool
Agritourism in val d'orcia

Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is ￥27,596
￥62,551 total
includes taxes & fees
Dec 27 - Dec 28
Agritourism in val d'orcia
Dining
Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino
Montalcino
9.0 out of 10, Wonderful, (4)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
The price is ￥22,041
￥25,714 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Podere Belsogno-camera Rosmarino
Property grounds
Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Room 'Camera Rossa' with Shared Terrace and Wi-Fi
Montalcino
10.0 out of 10, Exceptional, (1)
"Host was very very kind and generous, very glad to have booked with her. No AC, but fan and open windows made it very comfortable"
United States
Sam
The price is ￥21,281
￥22,016 total
includes taxes & fees
Dec 27 - Dec 28
Room 'Camera Rossa' with Shared Terrace and Wi-Fi
Property grounds
La Casetta di Nise - Charming Private spa in the Borgo

La Casetta di Nise - Charming Private spa in the Borgo

La Casetta di Nise - Charming Private spa in the Borgo
Castelnuovo dell'Abate
8.0 out of 10, Very Good, (1)
"This property was beautiful once we were able to find it, check in was a breeze and we were able to check in early. Tub and sauna great but not enough towels (no washer on premisis) but beautiful area "
United States
P.J. B.
The price is ￥27,596
￥36,243 total
includes taxes & fees
Jan 15 - Jan 16, 2026
La Casetta di Nise - Charming Private spa in the Borgo
Outdoor dining
Podere Belsogno-apartment rose garden

Podere Belsogno-apartment rose garden

Podere Belsogno-apartment rose garden
Montalcino
The price is ￥22,041
￥25,347 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Podere Belsogno-apartment rose garden
Fridge, oven, stovetop, dishwasher
Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment 'Casa Francesca' with Hills View & Courtyard
Montalcino
10.0 out of 10, Exceptional, (2)
"Clean property and amazing view. Great location "
United States
Angela B.
The price is ￥30,290
￥31,026 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Apartment 'Casa Francesca' with Hills View & Courtyard
Outdoor pool
Antico Brunello

Antico Brunello

Antico Brunello
Montalcino
The price is ￥1,212,254
￥1,335,317 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Antico Brunello
Outdoor dining
Podere Belsogno

Podere Belsogno

Podere Belsogno
Montalcino
10.0 out of 10, Exceptional, (1)
"Charming and attentive hosts, stunning terrace with amazing views and a modern, attractive and well equipped rental that was a short walk to downtown Montalcino. We had a fabulous time and would go back again."
Canada
David P.
The price is ￥64,391
￥73,590 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Podere Belsogno
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 Brunello di Montalcino Wine Area Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
Kenneth 3-night trip
Posted 5 days ago
Hotel Chiusarelli

Find out more about Brunello di Montalcino Wine Area

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

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

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

Explore a world of travel with Expedia