A hillside town with historic buildings and a prominent church.

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Montepulciano holiday 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, (117 reviews)
"It was very well located ."
Canada
Marlenne
The price is ฿5,474
฿6,175 total
includes taxes & fees
23 Sept - 24 Sept
Meublé Il Riccio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

2. 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 ฿9,843
฿10,981 total
includes taxes & fees
18 Sept - 19 Sept
Il Tosco
A crowded restaurant with brick walls and multiple tables and chairs.

3. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (147 reviews)
"Incredible views from our room"
United Kingdom
Isabelle
The price is ฿7,438
฿8,336 total
includes taxes & fees
27 Sept - 28 Sept
La Locanda di San Francesco
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

4. 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 ฿4,518
฿5,123 total
includes taxes & fees
23 Sept - 24 Sept
Bed & Breakfast Vicolo dell'Oste
A terrace with a table set for breakfast, overlooking a scenic landscape.

5. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (43 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ฿6,506
฿7,310 total
includes taxes & fees
6 Oct - 7 Oct
Delcorto Suites
An arched doorway leading to a building with a wooden door and a staircase.

6. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (109 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 ฿3,038
฿3,495 total
includes taxes & fees
13 Oct - 14 Oct
Residenza Fabroni

7. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful place, view and city."
United States
Federico
The price is ฿3,866
฿4,406 total
includes taxes & fees
3 Oct - 4 Oct
montorio
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, (4 reviews)
"I wish I knew more about the check in process ahead of time of that they contacted me ok WhatsApp. But it was clean, comfortable, as pictured, great location, and a great stay. "
United States
Nicole
The price is ฿2,330
฿2,717 total
includes taxes & fees
1 Oct - 2 Oct
Bellarmino Boutique Apartments
A patio area with outdoor seating, potted plants, and a view of the landscape.

9. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (66 reviews)
"A fantastic stay in such a beautiful part of Tuscany. Hosts were friendly and went out of their way to help. Breakfast was lovely and the room was clean and comfortable. Would highly recommend!"
United Kingdom
Christopher
The price is ฿3,724
฿5,053 total
includes taxes & fees
4 Oct - 5 Oct
Affitacamere Maria Gabriella
A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

10. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ฿3,464
฿3,964 total
includes taxes & fees
16 Oct - 17 Oct
PienzaLettings Suites
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

11. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (101 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is ฿4,463
฿5,063 total
includes taxes & fees
1 Oct - 2 Oct
B&B Le Scalette di Piazza
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

12. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (155 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ฿7,186
฿8,135 total
includes taxes & fees
10 Oct - 11 Oct
Hotel San Gregorio
A historic building with a tower, a courtyard, and a well-lit entrance.

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (181 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿4,610
฿5,186 total
includes taxes & fees
12 Oct - 13 Oct
Abbadia Sicille Relais
A poolside area with two glasses of water, candles, and a stone pathway.

14. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (95 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ฿6,146
฿6,914 total
includes taxes & fees
20 Sept - 21 Sept
Casanova - Panoramic Rooms and Suites
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

15. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is ฿3,802
฿4,335 total
includes taxes & fees
15 Oct - 16 Oct
TuscanyLettings Studio&Room
A bakery display with various pastries and desserts.

16. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (13 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is ฿4,081
฿4,565 total
includes taxes & fees
17 Sept - 18 Sept
La Piccola Locanda
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

17. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (38 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is ฿3,152
฿3,620 total
includes taxes & fees
17 Sept - 18 Sept
Residence al Lago

18. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is ฿4,497
฿5,101 total
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
A stone building with a wooden door, a staircase, and a small window with a metal grill.

19. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is ฿3,889
฿4,432 total
includes taxes & fees
12 Oct - 13 Oct
Casa Gioia - Casa Olivieri
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

20. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ฿24,200
฿26,774 total
includes taxes & fees
17 Sept - 18 Sept
L'Olmo
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

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"All good"
D 2-night trip
Posted 2 days ago
Nuovo Etruria Resort

Find out more about Montepulciano

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

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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 43 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 Palazzo Ricci 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.