A hillside town with historic buildings and a prominent church.

Search Holiday Rentals in Montepulciano

  • 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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Montepulciano holiday rentals

An outdoor dining table with a meal consisting of bread, tomatoes, and cured meat, accompanied by a glass of white wine.

1. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is 3.585.435 ₫
4.057.477 ₫ total
includes taxes & fees
26 Nov - 27 Nov
La Locanda di San Francesco
An arched doorway leading to a building with a wooden door and a staircase.

2. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (117 reviews)
"Was a very nice spot"
Canada
Andrew
The price is 2.091.316 ₫
2.413.795 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Residenza Fabroni
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

3. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is 2.399.547 ₫
2.752.849 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Bed & Breakfast Vicolo dell'Oste
An interior courtyard with stone columns, arches, and a mosaic.

4. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 reviews)
"The room was beautifully designed, clean and fresh with stunning views in a truly historic building. Family run and a special experience!!"
United States
Slimane
The price is 4.037.971 ₫
4.555.116 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Meublé Il Riccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

5. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is 4.319.276 ₫
4.864.551 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Delcorto Suites
A stone building with a tiled roof, surrounded by tall trees and a gravel path.

6. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (13 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is 3.037.121 ₫
3.454.237 ₫ total
includes taxes & fees
13 Dec - 14 Dec
montorio
A stone archway leading to a building entrance with a wooden door.

7. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (5 reviews)
"Na"
United States
Abel
The price is 1.480.099 ₫
1.741.608 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Bellarmino Boutique Apartments
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

8. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (142 reviews)
"Amazing location, unique and beautiful setting, unforgettable delicious plentiful breakfast, and the kindest hoteliers one could imagine."
United States
Janine
The price is 5.850.361 ₫
6.548.896 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Il Tosco
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 Montepulciano Hotel Reviews

Il Tosco

Il Tosco

10/10 Excellent
"Amazing location, unique and beautiful setting, unforgettable delicious plentiful breakfast, and the kindest hoteliers one could imagine."
Janine 3-night trip
Posted 20 hours ago
Il Tosco

Frequently asked questions

Are there holiday rentals in Montepulciano?

Yes, there are holiday rentals close to the most popular sights in Montepulciano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Montepulciano speak positively about the countryside and wineries in this destination. Make sure you have time to check out the sightseeing tours and festivals during your trip.

How many holiday rentals are there in Montepulciano?

Expedia has 48 holiday rentals for your stay in Montepulciano.

What’s there to see and do in Montepulciano?

Terme di Montepulciano Spa and Val di Chiana are a couple of scenic spots to enjoy the outdoors, whereas Civic Museum is one of the cultural attractions. While here, Palazzo Avignonesi and Cantina del Redi are other places worth a visit.

What’s a holiday rental in Montepulciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montepulciano. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.