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Toppole 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 Toppole vacation rentals

A rustic outdoor dining area with wooden tables and chairs, hanging birdcages, and a view of greenery.

1. Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi

Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi
ANGHIARI
10.0 out of 10, Exceptional, (1 review)
"I greatly enjoyed my stay at this beautiful and unique apartment. It was captivatingly decorated with antiques and appointed with all needed amenities. the hosts were charming and helpful, and made every effort to make me feel at home and my stay comfortable. If I had the time, I believe a longer stay would have been quite pleasant."
United States
Andrew P.
$119 nightly
The price is $122
Sep 23 - Sep 24
Total with taxes and fees
Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi

2. 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
$86 nightly
The price is $102
Oct 13 - Oct 14
Total with taxes and fees
iConic Wellness Resort
A grassy courtyard with a stone wall, a wooden bench, and a building with a tower in the background.

3. Apartment 'Sotto Le Mura' with Wi-Fi

Apartment 'Sotto Le Mura' with Wi-Fi
Anghiari
$115 nightly
The price is $115
Sep 24 - Sep 25
Total with taxes and fees
Apartment 'Sotto Le Mura' with Wi-Fi
A balcony with a view of a sunset over a hilly landscape.

4. Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.

Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.
Toscana
9.4 out of 10, Exceptional, (3 reviews)
"Great appartment really nice. Great view. Very nice and reactive owner.However it is imperative to have a car to go there, even by walking very fast it takes minimum 50 minutes to go to the center.And also take note that there are stairs to get to the appartment."
United States
Louis / Jeanne M.
$114 nightly
The price is $118
Sep 27 - Sep 28
Total with taxes and fees
Stunning Loft nestled in the Tuscan countryside 15 minutes walk from the center.
A rustic room with a stone wall, a spiral staircase, a bed, a table with chairs, and a small kitchen area.

5. Apartment Room with a View in Anghiari

Apartment Room with a View in Anghiari
Anghiari
$252 nightly
The price is $252
Sep 27 - Sep 28
Total with taxes and fees
Apartment Room with a View in Anghiari
A table set outdoors with a view of mountains, including a basket of pastries, cups of coffee, and a bottle of water.

6. Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6 reviews)
"客室は清潔で、とても可愛いかったです。宿泊場所からの眺望は感動します。 朝食が人生でベスト朝食でした！"
Japan
Tatsuya
$125 nightly
The price is $138
Sep 24 - Sep 25
Total with taxes and fees
Locanda del Viandante
A view of a historic town with prominent buildings and a church tower.

7. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (192 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
$84 nightly
The price is $99
Oct 15 - Oct 16
Total with taxes and fees
Cameracaffè Centro

8. Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi

Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
Anghiari
$126 nightly
The price is $126
Sep 27 - Sep 28
Total with taxes and fees
Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
A room with a stone archway, wooden ceiling beams, a bed, a chair, a table, and a window with curtains.

9. Cozy apartment: Your oasis of paradise in the countryside

Cozy apartment: Your oasis of paradise in the countryside
Anghiari
$142 nightly
The price is $142
Sep 24 - Sep 25
Total with taxes and fees
Cozy apartment: Your oasis of paradise in the countryside
A stone building with arched windows and a gravel driveway.

10. Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
$109 nightly
The price is $124
Oct 23 - Oct 24
Total with taxes and fees
Villa La Ginestra
A stone building with a pool, surrounded by trees and outdoor seating.

11. -2 / 3-seater garage with private garden, swimming pool, park and spa

-2 / 3-seater garage with private garden, swimming pool, park and spa
sansepolcro (arezzo)
9.6 out of 10, Exceptional, (4 reviews)
"Es waren traumhafte Tage. So extrem ruhig ..... Richtig entspannend. Alles da zur Selbstversorgung an Küchenutensilien. Alles sehr sauber. Der Besitzer sehr freundlich und bemüht. Wir fahren nächstes Jahr wieder hin ..... Aber länger. Sehr empfehlenswert"
Austria
Margit H.
$177 nightly
The price is $177
Sep 24 - Sep 25
Total with taxes and fees
-2 / 3-seater garage with private garden, swimming pool, park and spa
A spacious living area with a red sofa, a fireplace, and a herringbone-patterned floor.

12. Teo's house is the ideal home for relaxation, centrally located in Anghiari

Teo's house is the ideal home for relaxation, centrally located in Anghiari
Anghiari
10.0 out of 10, Exceptional, (1 review)
"The apartment was clean and cozy. I thoroughly enjoyed my stay. It is located on Corso Giacomo Matteotti and directly across from the main town square. Although not in the walled, traditional historic center, its in a very convenient and central location for exploring the entire town. The host Francesca was extremely helpful and checked in often."
United States
Danna J.
$255 nightly
The price is $255
Oct 1 - Oct 2
Total with taxes and fees
Teo's house is the ideal home for relaxation, centrally located in Anghiari
A building with a balcony, multiple windows, and a door.

13. Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13 reviews)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
$56 nightly
The price is $62
Oct 12 - Oct 13
Total with taxes and fees
Dolce Rosa Centro Storico
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

14. Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
9.4 out of 10, Exceptional, (29 reviews)
"Ich kam spät an und die warme Atmosphäre traf mich sofort. Das gemütliche Wohnzimmer mit einem Kamin war perfekt für unsere Gruppe, um sich nach der Erkundung von Città di Castello zu entspannen. Wir kochten gemeinsam in der geräumigen Küche, die alles hatte, was wir brauchten. Die Mahlzeiten draußen im Garten mit Grillmöglichkeiten zu genießen, machte es noch besser. Insgesamt ein großartiger Wert für das, was man bekommt."
Germany
Anonymous traveler
$289 nightly
The price is $289
Sep 30 - Oct 1
Total with taxes and fees
Elegant Countryside Retreat
A narrow street with buildings on either side, stone walls, and a clear blue sky.

15. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
$162 nightly
The price is $169
Oct 1 - Oct 2
Total with taxes and fees
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A modern hotel room with large windows, a bed, a desk, and a chair.

16. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (81 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
$65 nightly
The price is $79
Sep 30 - Oct 1
Total with taxes and fees
B&B 52cento

17. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
$80 nightly
The price is $100
Sep 30 - Oct 1
Total with taxes and fees
Bibi Boutique
A hotel room with a bed, two bedside lamps, a window with curtains, and a wall-mounted picture.

18. Alò - One Bedroom Apartment, Sleeps 2

Alò - One Bedroom Apartment, Sleeps 2
Arezzo
$138 nightly
The price is $145
Oct 6 - Oct 7
Total with taxes and fees
Alò - One Bedroom Apartment, Sleeps 2
A balcony with a table set for two, a view of historic stone buildings, and a castle in the background.

19. Apartment "La Finestra sul Fiume" with Private Terrace

Apartment "La Finestra sul Fiume" with Private Terrace
Subbiano
10.0 out of 10, Exceptional, (3 reviews)
"Pros: Tutto molto pulito, il proprietario si è rivelata una persona gentilissima e molto disponibile"
Italy
Anonymous traveler
$93 nightly
The price is $96
Oct 22 - Oct 23
Total with taxes and fees
Apartment "La Finestra sul Fiume" with Private Terrace
A rustic outdoor dining area with wooden tables and chairs, hanging birdcages, and a view of greenery.

20. Double Rooms 'Beb 1416' with Shared Terrace, Garden, and Wi-Fi

Double Rooms 'Beb 1416' with Shared Terrace, Garden, and Wi-Fi
ANGHIARI
$182 nightly
The price is $185
Sep 24 - Sep 25
Total with taxes and fees
Double Rooms 'Beb 1416' with Shared Terrace, Garden, and 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 Toppole Hotel Reviews

Hotel San Michele

Hotel San Michele

8/10 Good
"This is a charming hotel housed in a 15th century palazzo as close as you can get to the center of Cortona. The staff was pleasant and helpful. Plus you can pull your car up for luggage drop off - a real convenience in a town center where cars are otherwise restricted. Just note this hotel is in an old building. Not all rooms are serviced by elevator - some stairs required. And like any historic property the facilities have charming quirks - rooms but not all public facilities have A/C, lighting is low and there are no amenities on site other than a lovely buffet breakfast you can enjoy inside or in a garden setting. However its location steps from Cortona’s Piazza Republica, restaurants and shops make up for any shortcomings!"
Leanne 4-night trip
Posted 16 hours ago
Hotel San Michele

Find out more about Toppole

Everything you need to know about Toppole 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 Toppole 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 Toppole vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Toppole vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Toppole. 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 Toppole 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 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 Toppole rentals

At Expedia, we put the best Toppole 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 Toppole 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 Toppole 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 Toppole. 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

Are there vacation rentals in Toppole?

Yes, you can find vacation rentals near popular local attractions in Toppole, or you can go with a more remote option if you'd like a relaxing place to stay. Toppole is known for its wineries.

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

Holiday Home in Umbria with Pool: This vacation home rental outside of Toppole offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Toppole?

Explore the area and family-friendly sights such as Aboca Museum, or get out into nature at a spot like Piazza Guido Monaco. In the larger area, you’ll find Anghiari Historic Town Center and Madonna del Parto Museum.

What’s a vacation rental in Toppole like?

Vacation rentals are private properties where you can stay for several days or longer in Toppole. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip.