A hillside town with historic buildings and a prominent church.

Montepulciano Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Montepulciano vacation rentals

An interior courtyard with stone columns, arches, and a mosaic.

1. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is CA $208
CA $235 total
includes taxes & fees
Oct 11 - Oct 12
Meublé Il Riccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

2. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (46 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $246
CA $277 total
includes taxes & fees
Oct 6 - Oct 7
Delcorto Suites
An arched doorway leading to a building with a wooden door and a staircase.

3. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (111 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is CA $110
CA $128 total
includes taxes & fees
Oct 13 - Oct 14
Residenza Fabroni
A crowded restaurant with brick walls and multiple tables and chairs.

4. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (149 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 CA $268
CA $302 total
includes taxes & fees
Oct 17 - Oct 18
La Locanda di San Francesco
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

5. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is CA $151
CA $172 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
Front of property

6. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is CA $161
CA $184 total
includes taxes & fees
Oct 7 - Oct 8
montorio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

7. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is CA $331
CA $370 total
includes taxes & fees
Nov 2 - Nov 3
Il Tosco
A stone archway leading to a building entrance with a wooden door.

8. Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
5.6 out of 10, (5 reviews)
"Na"
United States
Abel
The price is CA $76
CA $90 total
includes taxes & fees
Nov 4 - Nov 5
Bellarmino Boutique Apartments
A double wooden door with a wrought iron gate, set in a stone archway, against a weathered wall.

9. Vicolo Nobile - Romantic Heart of Montepulciano

Vicolo Nobile - Romantic Heart of Montepulciano
Montepulciano
10.0 out of 10, Exceptional, (6 reviews)
"The room was excellent, clean, all amenities, great location and a beautiful smell that make feel so comfortable. Host was responsive and helpful at all the times."
United States
FEDERICO
The price is CA $175
CA $210 total
includes taxes & fees
Oct 11 - Oct 12
Vicolo Nobile - Romantic Heart of Montepulciano
A bedroom with a bed, a desk, a chair, a mirror, and a chandelier.

10. Elegant juniper suite with possibility of third bed

Elegant juniper suite with possibility of third bed
Montepulciano
9.6 out of 10, Exceptional, (4 reviews)
"Check is was very easy, room was spacious and clean. Parking lot P6 was relatively close and only cost 10 Euro/day. Air conditioner stopped working on the last day but that is no fault of the owners. I am sure it is fixed. I would stay here again if my wife and I return to Montepulciano."
United States
Dean B.
The price is CA $257
CA $257 total
includes taxes & fees
Oct 27 - Oct 28
Elegant juniper suite with possibility of third bed
A bedroom with a bed, a window with shutters, a radiator, and artwork on the wall.

11. Quadruple Room - Dill

Quadruple Room - Dill
Montepulciano
The price is CA $241
CA $250 total
includes taxes & fees
Nov 2 - Nov 3
Quadruple Room - Dill
A bedroom with a bed, two chairs, a nightstand, a dresser, a balcony with a railing, and a staircase.

12. Appartamento in Via dell'Opio nel Corso 47

Appartamento in Via dell'Opio nel Corso 47
Montepulciano
The price is CA $265
CA $354 total
includes taxes & fees
Oct 8 - Oct 9
Appartamento in Via dell'Opio nel Corso 47
A table with a coffee pot, cups, and newspapers on a balcony overlooking a hilly landscape.

13. Apartment 'Entro le mura' with Balcony & Wi-Fi

Apartment 'Entro le mura' with Balcony & Wi-Fi
Montepulciano
9.8 out of 10, Exceptional, (12 reviews)
"Everything was clean and neat. A lovely view. We received help with parking and luggage from Enrico, who also treated us to a bottle of wine. "
Canada
Heather M.
The price is CA $404
CA $491 total
includes taxes & fees
Oct 11 - Oct 12
Apartment 'Entro le mura' with Balcony & Wi-Fi
A terrace with a view of a bell tower, two wine glasses, and potted plants.

14. Apartment dell 'Erbe with panoramic terraces

Apartment dell 'Erbe with panoramic terraces
Montepulciano
10.0 out of 10, Exceptional, (45 reviews)
"Great stay and location with plenty of food/wine options nearby! We visited Siena and Assisi which were short drives from the apartment. Francy made sure everything was perfect and was quick to answer any questions. The apartment had plenty of space and was very clean. Check-in/check-out was easy and we will definitely stay here again on our next trip to Montepulciano! "
United States
david r.
The price is CA $561
CA $561 total
includes taxes & fees
Oct 25 - Oct 26
Apartment dell 'Erbe with panoramic terraces
A bedroom with a bed, a desk, a chair, a television, and a window with a view.

15. Room 'Camera tripla con bagno privato vicino Montepulciano'

Room 'Camera tripla con bagno privato vicino Montepulciano'
Montepulciano
The price is CA $208
CA $294 total
includes taxes & fees
Oct 12 - Oct 13
Room 'Camera tripla con bagno privato vicino Montepulciano'
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

16. Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is CA $173
CA $258 total
includes taxes & fees
Oct 7 - Oct 8
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A bedroom with a bed, a wooden headboard, a dresser, a painting, a vase with flowers, and a window with curtains.

17. Marjoram double room

Marjoram double room
Montepulciano
The price is CA $241
CA $241 total
includes taxes & fees
Oct 25 - Oct 26
Marjoram double room
A bedroom with a large bed, a chandelier, a desk, and a chair.

18. Premium Apartment - Helichrysum

Premium Apartment - Helichrysum
Montepulciano
The price is CA $513
CA $523 total
includes taxes & fees
Oct 21 - Oct 22
Premium Apartment - Helichrysum
A garden pathway leading to a brick building with a metal gate, surrounded by potted plants and rocks.

19. Apartment 'Casa Isidora' with Mountain View, Wi-Fi and Air Conditioning

Apartment 'Casa Isidora' with Mountain View, Wi-Fi and Air Conditioning
Acquaviva
The price is CA $217
CA $223 total
includes taxes & fees
Oct 6 - Oct 7
Apartment 'Casa Isidora' with Mountain View, Wi-Fi and Air Conditioning
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

20. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is CA $233
CA $319 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Home in Villa Pandolfina near Montepulciano
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 Montepulciano Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"A beautiful, luxury estate in the countryside. While we traveled as a couple, it seemed a popular destination for families with children. The restaurant on site was excellent and the rooms were well appointed and comfortable. We stayed in a junior suite which had stairs from the living room/bathroom up to the bedroom loft. *something to be aware of when booking"
Elizabeth 3-night trip
Posted 1 hour ago
Precise Tale Poggio Alla Sala

Find out more about Montepulciano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montepulciano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montepulciano?

Yes, we offer vacation rentals close to top sights in Montepulciano, or you can go with a more remote option if you're looking for relaxation. 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.

What are some of the best vacation home rentals that Montepulciano has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This highly rated vacation home rental in Montepulciano is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation. Another good choice for your trip to Montepulciano is Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano.

How many vacation rentals are there in Montepulciano?

Expedia has 48 vacation 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 vacation rental in Montepulciano like?

A vacation rental is a private property you can book for a few weeks or just a few days in Montepulciano. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.