Montecchio Vacation Rentals from CA $143: Short-Term Rentals for 2026

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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

Castiglion Fiorentino

Vern

CA $212 total

includes taxes & fees

Sep 1 - Sep 2

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

2. B&B Piccolo Hotel

Cortona Old Town

mansoor

CA $249 total

includes taxes & fees

Aug 28 - Aug 29

3. iConic Wellness Resort

Arezzo

Rheymarie

CA $176 total

includes taxes & fees

Aug 30 - Aug 31

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

Cortona Old Town

Julie R.

CA $158 total

includes taxes & fees

Sep 1 - Sep 2

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

5. CASA AMBRA

Cortona Old Town

CA $217 total

includes taxes & fees

Sep 17 - Sep 18

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

6. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

CA $410 total

includes taxes & fees

Sep 1 - Sep 2

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

7. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

CA $165 total

includes taxes & fees

Aug 28 - Aug 29

A view from a window overlooking a courtyard with stone buildings and a tower.

8. La Finestra sul Teatro

Cortona Old Town

Michelle H.

CA $319 total

includes taxes & fees

Sep 3 - Sep 4

A park with picnic tables, a playground, and a gravel path.

9. Holiday home with panoramic terrace ideal for families and couples

Cortona

CA $131 total

includes taxes & fees

Aug 28 - Aug 29

A staircase with two lit lanterns on the wall.

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

Cortona Old Town

Erin

CA $233 total

includes taxes & fees

Sep 9 - Sep 10

A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

11. Cortonas Rooftop Nest

Cortona Old Town

Robin F.

CA $297 total

includes taxes & fees

Aug 29 - Aug 30

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

12. Dolce Casa 2 by Tiny Away

Rigutino

CA $172 total

includes taxes & fees

Sep 9 - Sep 10

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

13. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

CA $129 total

includes taxes & fees

Sep 1 - Sep 2

14. Montecchio di Cortona

Montecchio

Monica S.

CA $157 total

includes taxes & fees

Sep 1 - Sep 2

A spa area with a stone-walled arch, a hot tub, and a small window.

15. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $200 total

includes taxes & fees

Sep 24 - Sep 25

16. Dolce Casa 1 by Tiny Away

Rigutino

CA $182 total

includes taxes & fees

Aug 30 - Aug 31

A view through a window with a mesh screen, displaying a sunset sky and buildings in the background.

17. La casa di Laura

Cortona Old Town

"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...

Angie F.

CA $279 total

includes taxes & fees

Sep 14 - Sep 15

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

18. Abbadia Sicille Relais

Trequanda

Robert

CA $269 total

includes taxes & fees

Sep 27 - Sep 28

An arched stone bridge with a white building on the right, featuring a balcony with plants.

19. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

CA $179 total

includes taxes & fees

Sep 26 - Sep 27

A view of a historic town with prominent buildings and a church tower.

20. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

CA $141 total

includes taxes & fees

Aug 28 - Aug 29

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Top Montecchio Hotel Reviews

Precise Tale Poggio Alla Sala

10/10 Excellent

"Amazing! If you are a family visiting Tuscany I highly recommend"

Il Verreno

8/10 Good

"The staff was very helpful and accommodating. (5stars) The food at the restaurant (dinner) is phenomenal, one of the best meals during my trip. I highly recommend scheduling an onsite wine tasting with their sommelier as well. (5stars) The rooms are large and very spacious. Bathrooms are dated. (3.5 stars) The location of the property is removed with limited access to resources outside of the property (water, food, shopping, etc). (3 star)"

Hotel Villa Ricci

10/10 Excellent

"The staff was so incredibly friendly and accommodating. They were ready with recommendations, patient with our lack of Italian knowledge, and always smiling when we entered. The spa is so lovely and relaxing, and reasonably priced. Breakfast spread is lovely and served fairly late into the morning. Walkable to multiple delicious restaurants nearby. We would definitely recommend this hotel if you’re visiting Tuscany."

Villa Tiberini Wine Relais

10/10 Excellent

"We stayed four nights at Villa Tiberini and loved it! Everyone was super friendly and helpful, nice breakfast with delicious eggs, the apartment was beautiful with everything we needed and the grounds were beautiful. We especially loved the pool. It’s in a great position for exploring near by. Highly recommended!!"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montecchio vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montecchio vacation rentals we have selected for you start as low as CA $143 per night. Entering your travel dates in the search wizard 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?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental outside of Montecchio 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.

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. Cortona Cathedral and Santa Maria Nuova 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.

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Check prices for these dates

Our top choices for Montecchio vacation rentals

1. San Michele al Borgo

2. B&B Piccolo Hotel

3. iConic Wellness Resort

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

5. CASA AMBRA

6. Fontelunga Hotel & Villas

7. Vicolo Della Scala Rooms - La Luna

8. La Finestra sul Teatro

9. Holiday home with panoramic terrace ideal for families and couples

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

11. Cortonas Rooftop Nest

12. Dolce Casa 2 by Tiny Away

13. Artisti del Cavallo Tourism

14. Montecchio di Cortona

15. DormiVeglia B&B

16. Dolce Casa 1 by Tiny Away

17. La casa di Laura

18. Abbadia Sicille Relais

19. Locanda Antico Borgo

20. Cameracaffè Centro

Find vacation rentals that suit your style

Top Montecchio Hotel Reviews

Precise Tale Poggio Alla Sala

Il Verreno

Monastero di Cortona Hotel & Spa

Villa di Piazzano - Small Luxury Hotel of the World

Grand Hotel Admiral Palace

Il Gentiluomo Hotel & SPA

Hotel Minerva

Hotel Villa Ricci

Villa Tiberini Wine Relais

Find out more about Montecchio

Frequently asked questions

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