A historic castle on a hill with a church and a tower in the foreground.

Montecchio Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Montecchio vacation rentals

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

1. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
$126 nightly
The price is $143
Oct 1 - Oct 2
Total with taxes and fees
San Michele al Borgo
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

2. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
$283 nightly
The price is $316
Oct 11 - Oct 12
Total with taxes and fees
Fontelunga Hotel & Villas
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

3. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$155 nightly
The price is $175
Sep 29 - Sep 30
Total with taxes and fees
B&B Piccolo Hotel
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

4. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
$106 nightly
The price is $111
Sep 28 - Sep 29
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

5. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
$226 nightly
The price is $253
Oct 24 - Oct 25
Total with taxes and fees
Castello di Gargonza
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

6. CASA AMBRA

CASA AMBRA
Cortona Old Town
$290 nightly
The price is $323
Oct 16 - Oct 17
Total with taxes and fees
CASA AMBRA

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$75 nightly
The price is $90
Oct 25 - Oct 26
Total with taxes and fees
iConic Wellness Resort
A view from a window overlooking a courtyard with stone buildings and a tower.

8. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
$205 nightly
The price is $209
Oct 4 - Oct 5
Total with taxes and fees
La Finestra sul Teatro
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

9. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
$210 nightly
The price is $213
Sep 28 - Sep 29
Total with taxes and fees
Cortonas Rooftop Nest
A spa area with a stone-walled arch, a hot tub, and a small window.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$111 nightly
The price is $127
Oct 11 - Oct 12
Total with taxes and fees
DormiVeglia B&B
A historic building with a tower, a courtyard, and a well-lit entrance.

11. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
$112 nightly
The price is $126
Oct 25 - Oct 26
Total with taxes and fees
Abbadia Sicille Relais
An arched doorway leading to a building with a wooden door and a staircase.

12. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 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
$101 nightly
The price is $115
Oct 13 - Oct 14
Total with taxes and fees
Residenza Fabroni
A staircase with two lit lanterns on the wall.

13. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
$162 nightly
The price is $165
Sep 30 - Oct 1
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & balcony)
A building with a stone facade, multiple windows, and a balcony.

14. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
$464 nightly
The price is $469
Oct 5 - Oct 6
Total with taxes and fees
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

15. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
$122 nightly
The price is $122
Sep 27 - Sep 28
Total with taxes and fees
Dolce Casa 2 by Tiny Away
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

16. 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
$78 nightly
The price is $90
Oct 25 - Oct 26
Total with taxes and fees
Artisti del Cavallo Tourism
An interior courtyard with stone columns, arches, and a mosaic.

17. 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
$149 nightly
The price is $169
Oct 25 - Oct 26
Total with taxes and fees
Meublé Il Riccio
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

18. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$99 nightly
The price is $113
Sep 28 - Sep 29
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A building with a stone facade, multiple windows, and a balcony.

19. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
$333 nightly
The price is $339
Oct 5 - Oct 6
Total with taxes and fees
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & 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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Top Montecchio Hotel Reviews

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"The staff was very attentive and helpful specially Alfredo. He is terrific! My only complaint was a persistent low level hum that was noticeable at night, I figured that our room was above the kitchen area and that it was the industrial size refrigerator below. The view of the town up the hill from our room was spectacular. Decent breakfast. The pool was wonderful."
Robert 2-night trip
Posted 2 days ago
Nuovo Etruria Resort

Find out more about Montecchio

Everything you need to know about Montecchio vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montecchio vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montecchio vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecchio vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecchio. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montecchio in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montecchio rentals

At Expedia, we put the best Montecchio vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montecchio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montecchio vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montecchio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Montecchio?

Yes, we offer vacation rentals near top local attractions in Montecchio, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Montecchio?

Villa Banditello, secluded, panoramic view over Montepulciano valley.: This vacation home rental outside of Montecchio is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Montecchio?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Montecchio stay.

What’s there to see and do in Montecchio?

While you're exploring the area, Piazza Guido Monaco and Isola Maggiore are a couple of picturesque spots to get outside and enjoy nature. Tennis Club Castiglionese and Cortona Cathedral are a couple of places you'll find in the larger area.

What’s a vacation rental in Montecchio like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Montecchio. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.