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Brunello di Montalcino Wine Area Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Brunello di Montalcino Wine Area holiday rentals

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

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Property grounds
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (67)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,371
HK$1,855 total
includes taxes & fees
11 Jan - 12 Jan 2026
The House of Alice, charm and relaxation
Terrace/patio
Antico Brunello

Villa in Montalcino

Antico Brunello
The price is HK$60,317
HK$66,440 total
includes taxes & fees
16 Dec - 17 Dec
Antico Brunello
Food and drink
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is HK$1,607
HK$1,823 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is HK$519
HK$607 total
includes taxes & fees
22 Dec - 23 Dec
ApartHotel Anghel
Terrace/patio
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$563
HK$647 total
includes taxes & fees
16 Dec - 17 Dec
Abbadia Sicille Relais
Premium bedding, down duvets, pillow-top beds, minibar
Tuscasì Aparthotel

Aparthotel in Sovicille

Tuscasì Aparthotel
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is HK$515
HK$685 total
includes taxes & fees
20 Dec - 21 Dec
Tuscasì Aparthotel
Tasting room
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
1 treatment room, massages
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is HK$1,759
HK$1,972 total
includes taxes & fees
26 Dec - 27 Dec
Casanova - Panoramic Rooms and Suites
Property grounds
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Villa in chiusi

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Exterior detail
agriturismo la roggiola

Cottage in Monticiano

agriturismo la roggiola
9.6 out of 10, Exceptional, (112)
"A Nice Home in nature with a lot of animals."
Germany
Tabea S.
agriturismo la roggiola
Daily continental breakfast (EUR 20 per person)
Residenza d'Epoca Palazzo Borghesi

Residence in Siena City Centre

Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is HK$1,436
HK$1,617 total
includes taxes & fees
15 Jan - 16 Jan 2026
Residenza d'Epoca Palazzo Borghesi
City view
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Property grounds
Il Poggio dell'Eremita

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is HK$1,258
HK$1,459 total
includes taxes & fees
26 Dec - 27 Dec
Il Poggio dell'Eremita
Exterior
Camping Siena Colleverde

Camping in Scacciapensieri

Camping Siena Colleverde
3.0 star property
8.2 out of 10, Very good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Indoor pool, a heated pool
Private House with Exclusive Swimming Pool Heated and Amazing View

Holiday Home in Boccheggiano

Private House with Exclusive Swimming Pool Heated and Amazing View
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
The price is HK$26,503
HK$31,438 total
includes taxes & fees
31 Dec - 1 Jan 2026
Private House with Exclusive Swimming Pool Heated and Amazing View
Outdoor dining
Gite Montemirello, with garden and swimming pool

Apartment in Casciano di Murlo - Siena

Gite Montemirello, with garden and swimming pool
9.8 out of 10, Exceptional, (60)
"Very nice stay and very nuce Host :)"
Germany
Timo
Gite Montemirello, with garden and swimming pool
Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is HK$777
HK$891 total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments
Property entrance
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is HK$698
HK$804 total
includes taxes & fees
16 Dec - 17 Dec
Residenza Fabroni
Exterior
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino

Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
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 Brunello di Montalcino Wine Area Hotel Reviews

Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo

10/10 Excellent
"We had a lovely stay here. It's a short drive from town and a beautiful property. We did a wine tasting of the delicious estate wines and a cooking class as well. The room is spacious, comfortable, and well decorated. The staff is really attentive and took great care of us, giving us advice on where to go, helping us get the car to town and make reservations, etc. We used the hot tub which was fantastic. Thanks for a great relaxing stay!"
Marysa 3-night trip
Posted 7 days ago
Villa Le Prata - Residenza del Vescovo

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