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Nov 20 - Nov 22
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Dec 11 - Dec 13
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Jan 8 - Jan 10

Our top choices for Montalcino villas

A stone building with a garden pathway leading to it.

1. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is CA $9,348
CA $10,140 total
includes taxes & fees
Nov 12 - Nov 13
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
A stone building with multiple rooms, surrounded by lush greenery and trees.

2. WPRELAIS BORGO VIGNALUNGA

WPRELAIS BORGO VIGNALUNGA
Toscana
10.0 out of 10, Exceptional, (39 reviews)
"This villa is amazing! The views are spectacular. The home is awesome! The property is beautiful! "
United States
Jeremy F.
The price is CA $1,048
CA $1,565 total
includes taxes & fees
Nov 22 - Nov 23
WPRELAIS BORGO VIGNALUNGA
A stone house with a tiled roof, a small porch, and potted plants.

3. Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10

Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10
Montenero
The price is CA $439
CA $832 total
includes taxes & fees
Nov 14 - Nov 15
Quercetino: Authentic Tuscan country house near Val d'Orcia & hot springs - Sleeps 10
A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

4. Wp Relais Villa Vignalunga

Wp Relais Villa Vignalunga
CASTIGLIONE D'ORCIA (SI)
10.0 out of 10, Exceptional, (58 reviews)
"Amazing place to stay!! Absolutely beautiful home with unbeatable views of the countryside. The pool was wonderful to come home to after exploring. The host was also super responsive and helped us set up an amazing cooking class/dinner which far far exceeded our expectations. I wouldn’t stay anywhere else if I ever come back to Tuscany!!"
United States
Samantha L.
The price is CA $1,046
CA $1,201 total
includes taxes & fees
Nov 30 - Dec 1
Wp Relais Villa Vignalunga
A stone building with a tiled roof, a small porch, and a pathway leading to it.

5. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
San Quirico d'Orcia
The price is CA $2,817
CA $2,920 total
includes taxes & fees
Nov 30 - Dec 1
Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

6. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $220
CA $242 total
includes taxes & fees
Nov 17 - Nov 18
Il Poggio dell'Eremita
A two-story building with balconies, outdoor seating, and potted plants.

7. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $114
CA $132 total
includes taxes & fees
Nov 15 - Nov 16
Artisti del Cavallo Tourism
A courtyard with a pathway, a small pool, and a variety of trees and shrubs.

8. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
Trequanda
The price is CA $305
CA $372 total
includes taxes & fees
Nov 14 - Nov 15
Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w
A stone building with a car parked in front, surrounded by trees and a gravel path.

9. Charming Tuscan villa with a private infinity pool

Charming Tuscan villa with a private infinity pool
Castel del Piano
The price is CA $1,711
CA $1,958 total
includes taxes & fees
Nov 15 - Nov 16
Charming Tuscan villa with a private infinity pool
A tree, a lamp post, and a clear blue pool with a view of distant mountains.

10. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
Torrita di Siena
10.0 out of 10, Exceptional, (1 review)
"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."
United States
Nate D.
The price is CA $3,054
CA $3,058 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi
A large, red-roofed villa surrounded by lush green fields and rolling hills.

11. '...a delicious farmhouse in the countryside where only the wind blows...'

'...a delicious farmhouse in the countryside where only the wind blows...'
Campiglia d'Orcia
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...
United States
Li-Shen L.
The price is CA $1,355
CA $2,179 total
includes taxes & fees
Nov 15 - Nov 16
'...a delicious farmhouse in the countryside where only the wind blows...'
A patio table with a patterned tablecloth, an umbrella, and metal chairs.

12. Villa Falco-Cignella Resort Apartments in Tuscany

Villa Falco-Cignella Resort Apartments in Tuscany
Trequanda
The price is CA $450
CA $455 total
includes taxes & fees
Nov 13 - Nov 14
Villa Falco-Cignella Resort Apartments in Tuscany
A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

13. Red Heart - Relax with Your Loved Ones in Tuscany

Red Heart - Relax with Your Loved Ones in Tuscany
Trequanda
The price is CA $784
CA $1,287 total
includes taxes & fees
Nov 12 - Nov 13
Red Heart - Relax with Your Loved Ones in Tuscany
A patio with a table and chairs, a large umbrella, and a vase of flowers.

14. Villa Cielo- Cignella Resort Tuscany Accommodation

Villa Cielo- Cignella Resort Tuscany Accommodation
Trequanda
The price is CA $454
CA $459 total
includes taxes & fees
Nov 12 - Nov 13
Villa Cielo- Cignella Resort Tuscany Accommodation
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

15. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is CA $11,218
CA $12,010 total
includes taxes & fees
Nov 12 - Nov 13
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A house with a stone wall, a large tree, and a patio area with a bench and table.

16. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
Roccastrada GR
The price is CA $2,007
CA $2,111 total
includes taxes & fees
Nov 12 - Nov 13
Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi
A well-lit courtyard with a stone pathway leading to a building with a large arched entrance.

17. VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Cortona
The price is CA $9,909
CA $9,909 total
includes taxes & fees
Nov 18 - Nov 19
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
A building with a red facade, green shutters, and a tiled roof.

18. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
Trequanda
The price is CA $884
CA $889 total
includes taxes & fees
Nov 12 - Nov 13
Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi
A building with arched windows and a hammock in the garden.

19. Villa Aquila-Cignella Resort Acommodation Tuscany

Villa Aquila-Cignella Resort Acommodation Tuscany
Trequanda
The price is CA $756
CA $761 total
includes taxes & fees
Nov 13 - Nov 14
Villa Aquila-Cignella Resort Acommodation Tuscany
A house with a patio, outdoor seating, and a view of the landscape.

20. Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi

Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
Trequanda
The price is CA $856
CA $860 total
includes taxes & fees
Nov 16 - Nov 17
Chalet "Villa Falco" with Shared Pool, Private Terrace & Wi-Fi
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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Learn more about Montalcino

Medieval stone walls surround this hilltop town where Brunello wine tastings await in historic cellars beneath the fortress. Climb the Torre del Palazzo Comunale for valley views, then sample local pecorino cheese and honey at shops along the narrow lanes.

See all hotels in Montalcino
A historic castle on a hill with surrounding greenery and buildings.

Frequently Asked Questions

How much do villas in Montalcino cost?

Prices for villas in Montalcino range between CA $113 and CA $11,217 per night. Whatever your budget, you can find a place that matches your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Montalcino?

You'll find villas in Montalcino. No matter if you're taking a trip with the kids or organizing a weekend break with friends, Expedia will help you find the ideal base for your squad.

Why book your villa in Montalcino with Expedia?

Reserving a villa in Montalcino is as simple as clicking on your travel dates and picking a place that has what you need. Looking for something upscale or budget friendly, or a stay that also includes WiFi and a hot tub? Use Expedia's search filters to narrow your results and find the ideal fit at the right price.

How can I find cheap villas in Montalcino?

Expedia is here to help you narrow your search for cheap villas in Montalcino. Simply use our convenient filter tool to select star rating, budget and amenities to refine your search and find a great place to stay in a few quick keystrokes.

What is there to do near my villa in Montalcino?

Montalcino has enough sights to keep you on the hop for weeks, starting with Castello Banfi. Museo del Tartufo, Tenuta Greppo Franco Biondi Santi and Fortress of Montalcino are other popular attractions. If you're staying a while longer, Abbazia di Sant'Antimo and Poggio Antico will cap off your itinerary nicely.