A historic town with terracotta-roofed buildings, a prominent church, and rolling hills in the background.

Montepulciano Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Montepulciano vacation rentals

A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

1. La Locanda di San Francesco

Montepulciano

Colin

₩229,246 total

includes taxes & fees

Nov 26 - Nov 27

An arched doorway leading to a building with a wooden door and a staircase.

2. Residenza Fabroni

Montepulciano

Marc

₩139,051 total

includes taxes & fees

Nov 11 - Nov 12

A terrace with a table set for breakfast, overlooking a scenic landscape.

3. Delcorto Suites

Montepulciano

Denise

₩258,903 total

includes taxes & fees

Nov 11 - Nov 12

A balcony with a view of a historic town, featuring terracotta-roofed buildings and a prominent church tower.

4. Meublé Il Riccio

Montepulciano

Slimane

₩242,435 total

includes taxes & fees

Nov 11 - Nov 12

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a lamp, and a window with sheer curtains.

5. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Melissa

₩146,514 total

includes taxes & fees

Nov 15 - Nov 16

A stone building with a tiled roof, surrounded by tall trees and a gravel path.

6. montorio

Montepulciano

Joseph

₩183,843 total

includes taxes & fees

Nov 11 - Nov 12

A window with a view of a green landscape and hills.

7. Il Tosco

Montepulciano

Valerie

₩348,081 total

includes taxes & fees

Nov 24 - Nov 25

A breakfast table with a teapot, a cup, a plate with croissants, and a fruit bowl.

8. Bellarmino Boutique Apartments

Montepulciano

Abel

₩92,568 total

includes taxes & fees

Dec 1 - Dec 2

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Find vacation rentals that suit your style

Top Montepulciano Hotel Reviews

Delcorto Suites

Montepulciano

10/10 Excellent

LOVED the property! This was the first time the room was much larger and grander than the photos online. I would estimate 1000 square feet. The ceilings were absolutely stunning and were original from 500 years ago. The bathroom was huge with a fabulous shower. The breakfast was delicious with a great variety and high-quality food with fresh eggs from their farm, including delicious baked goods. Not only do I highly recommend, we hope to be back sometime soon. Arrivederci Montepulciano! Ciao

KAREN

Terra Antica Resort

Montepulciano

10/10 Excellent

Nikhil

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

Lupaia

Torrita di Siena

10/10 Excellent

This was the most amazing place to stay! This was our favorite stop on a 30-day trip to Greece, Italy and Switzerland. The surrounding countryside is stunning. Our room had a Turkish Bath - what a fun experience. We were a couple of weeks in to our vacation, and we were ready for some down time. Having a private little garden, overlooking the Tuscan hillside was WONDERFUL. The dinner we had on site was one of the best of our entire trip. Breakfast in the morning was an incredible display...

KC Traveler

La Locanda di San Francesco

Montepulciano

10/10 Excellent

Roy

Meublé Il Riccio

Montepulciano

10/10 Excellent

Slimane

A hotel room with a classic design, featuring a large bed, a sitting area with a table and chairs, and a wooden door with a brass handle.

Palazzo Carletti

Montepulciano

10/10 Excellent

Naomi

A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

Relais Villa Grazianella - UNA Esperienze

Montepulciano

10/10 Excellent

We were the only guests for 2 nights out of 3, at this lovely B&B on the estate of one of the best wineries in Tuscany. We had sumptuous room with a living room, bedroom and bathroom (nice shower!) all to ourselves. The staff were local women, who made a wonderful breakfast every day and told us of the life in Tuscany. The place was spotless, the food great, and it was so relaxing to come " home" to the vineyards every night, after seeing hordes of people in the towns we explored. One could...

RAP

A dining table with two wine glasses, a candle, and a bottle of champagne, overlooking a swimming pool and a tree.

Agriturismo Merigge Wellness & Spa

Montepulciano

10/10 Excellent

Francisco

montorio

Montepulciano

10/10 Excellent

Nuestra estadía fue maravillosa. La propiedad tiene una vista espectacular y transmite una tranquilidad increíble, perfecta para descansar y desconectarse. Todo estaba muy limpio, cómodo y bien cuidado. Además, nos encantó el hermoso detalle que nos dejaron al llegar; fue un gesto muy especial que nos hizo sentir bienvenidas. Sin duda, un lugar con muchísimo encanto al que volveríamos felices.

CAROLINA

An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.

Podere La Rocca

Montepulciano

10/10 Excellent

Our stay at Podere La Rocca was fabulous! The property is located in the rolling Tuscan hills just outside Montepulciano. The property is a working farm and vineyard with an onsite restaurant and pool. Our room was comfortable and clean. The bathroom was huge with a new jetted tub. We stayed on the second floor in a building with a large communal room with a fireplace. On the first floor of the same building was a rec room with a pool table. What made the stay was our experience at the...

Bed & Breakfast Vicolo dell'Oste

Montepulciano

10/10 Excellent

First of all the thing you should know is that the town is a walled city like most of the towns in Tuscany. It is difficult to know where to park when you first get there. We ended up parking down at the bottom of the hill and only bringing a couple of backpacks with us up to the room. When we got there Luisa and Guiseppe were so nice, Luisa even came with me to move my car to someplace closer, and when there were no more spots gave up her spot and had me park there and then drove us back up to...

Lance

Palazzo Tombesi Trecci

Montepulciano

10/10 Excellent

Mary Margaret

A room with a large window overlooking a scenic landscape.

Palazzo Nobile di San Donato

Montepulciano

10/10 Excellent

Our experience at Palazzo Nobile di Santa Donato exceeded our expectations. The photos show how lovely the inn is, but they cannot capture the warmth and the history of the Palazzo. Staying there felt as if we were on the inside of a piece of art. A delicious, generous breakfast was served in a beautiful room overlooking the Tuscan hills The hostess was gracious and willing to provide us with information and her time. We would highly recommend this place for anyone ... and we can't wait...

Sharon

A building entrance with the name "ALBERGO LA TERRAZZA" above a wooden door.

Hotel La Terrazza di Montepulciano

Montepulciano

10/10 Excellent

Rent a car and drive the Tuscan countryside and stay at this hotel in Montepulciano. Roberto and his wife (princess) Elda were amazing and entertaining hosts. The hotel is right in the shopping and dining district, and there are multiple streets and sights to explore. Every few blocks there is another perch from which to look out over the incredible countryside. The room was large and beautiful, and you can hear the shoppers and diners down below the window. Walk up to the Piazza Grande in...

Damon

Find out more about Montepulciano

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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.

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.

Montepulciano Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Montepulciano vacation rentals

1. La Locanda di San Francesco

2. Residenza Fabroni

3. Delcorto Suites

4. Meublé Il Riccio

5. Bed & Breakfast Vicolo dell'Oste

6. montorio

7. Il Tosco

8. Bellarmino Boutique Apartments

Find vacation rentals that suit your style

Top Montepulciano Hotel Reviews

Delcorto Suites

10/10 Excellent

Find out more about Montepulciano

Frequently Asked Questions

Are there vacation rentals in Montepulciano?

How many vacation rentals are there in Montepulciano?

What’s there to see and do in Montepulciano?

What’s a vacation rental in Montepulciano like?