A mountainous landscape with terraced fields, a winding road, and a village with traditional buildings.

Pennabilli Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pennabilli vacation rentals

A stone building with a sloped roof, a small porch, and a staircase leading to the entrance.

1. Sweet home in the forest with mountains view - perfect for family and relax

Sweet home in the forest with mountains view - perfect for family and relax
Emilia-Romagna
$127 nightly
The price is $127
Oct 24 - Oct 25
Total with taxes and fees
Sweet home in the forest with mountains view - perfect for family and relax
Outdoor dining

2. Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.

Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.
Sassocorvaro
$135 nightly
The price is $135
Oct 21 - Oct 22
Total with taxes and fees
Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.
A modern living room with a white sofa, a coffee table, and a TV mounted on the wall. There is a plant on the coffee table and a small shelf with decorative items.

3. Gio's Hygge Nest

Gio's Hygge Nest
Montegrimano
$123 nightly
The price is $123
Oct 20 - Oct 21
Total with taxes and fees
Gio's Hygge Nest
Two wine glasses on a table with a view of greenery and hills in the background.

4. Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi

Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi
Sant'Agata Feltria
$241 nightly
The price is $241
Oct 22 - Oct 23
Total with taxes and fees
Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi
A building with a balcony, multiple windows, and a door.

5. 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
$51 nightly
The price is $56
Nov 16 - Nov 17
Total with taxes and fees
Dolce Rosa Centro Storico
A terrace with a table and chairs overlooking a valley with vineyards.

6. Alloggio al San Girolamo

Alloggio al San Girolamo
Longiano
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful place and host. Comfortable bed and good size room with an amazing country view. Breakfast was well prepared with homemade breads. Highly recommended. "
United States
Sara
$100 nightly
The price is $110
Nov 6 - Nov 7
Total with taxes and fees
Alloggio al San Girolamo
A stone building with a pool, surrounded by trees and outdoor seating.

7. -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)
8.4 out of 10, Very good, (5 reviews)
"Het uitzicht was prima, het bed lag ook wel goed, maar ventilatie was niks, waardoor het S’nachts bloedheet was. Het was een verouderde garage, ik zou niemand aanraden dit te boeken. Van park en spa heb ik ook niks gezien."
Netherlands
Sjoukje
$185 nightly
The price is $185
Oct 20 - Oct 21
Total with taxes and fees
-2 / 3-seater garage with private garden, swimming pool, park and spa
A bedroom with a stone wall, a bed, a wardrobe, a balcony with chairs, and a view of buildings.

8. Le Terrazze sul Fiume

Le Terrazze sul Fiume
Santa Sofia
$86 nightly
The price is $94
Nov 19 - Nov 20
Total with taxes and fees
Le Terrazze sul Fiume
A room with a bed, a window, and a view of the outdoors.

9. Bubble room

Bubble room
Castelci
$392 nightly
The price is $392
Nov 2 - Nov 3
Total with taxes and fees
Bubble room
A courtyard with stone buildings, arched doorways, and outdoor seating.

10. B&B Corte dei Turchi

B&B Corte dei Turchi
Longiano
9.2 out of 10, Wonderful, (17 reviews)
"Great location and good quality restaurants."
United Kingdom
Murat
$70 nightly
The price is $77
Oct 20 - Oct 21
Total with taxes and fees
B&B Corte dei Turchi
A table set outdoors with a view of mountains, including a basket of pastries, cups of coffee, and a bottle of water.

11. Locanda del Viandante

Locanda del Viandante
Anghiari
9.2 out of 10, Wonderful, (7 reviews)
"This is really one of those Dinner destinations that has rooms to stay too! 🙂 Beautiful location, and great food, I would have liked to have stayed longer!"
United States
Kenneth
$128 nightly
The price is $140
Oct 20 - Oct 21
Total with taxes and fees
Locanda del Viandante
A wooden chair facing a scenic view of rolling hills and a mountain range under a clear sky.

12. Beautiful self-catering flat for rent in the country

Beautiful self-catering flat for rent in the country
URBANIA
9.2 out of 10, Wonderful, (37 reviews)
"We had an excellent time in this lovely, cosy and fully equipped accommodation. The host was extraordinarily kind and helpful so we felt welcome and at home."
Germany
Joerg G.
$129 nightly
The price is $129
Oct 20 - Oct 21
Total with taxes and fees
Beautiful self-catering flat for rent in the country
A rooftop terrace with a red building, a paved walkway, and a view of a forested hill.

13. Residence Città Ideale

Residence Città Ideale
Urbino
7.4 out of 10, Good, (6 reviews)
$73 nightly
The price is $86
Oct 22 - Oct 23
Total with taxes and fees
Residence Città Ideale
A balcony with a white sofa, a chair, and a TV on a cabinet.

14. Residence Aida

Residence Aida
3.0 star property
Rimini
9.6 out of 10, Exceptional, (4 reviews)
"Mr Andrea was an excellent host - very helpful and spoke good English- apartment was roomy and comfortable - only fault was no jug for making tea and no toaster"
United States
Jane
$61 nightly
The price is $73
Oct 20 - Oct 21
Total with taxes and fees
Residence Aida
A living room with a sofa, a dining area with a table and chairs, a kitchen visible through an open door, and pendant lights on the ceiling.

15. Tranquil 2-Bedroom Apartment in Historic Bagno di Romagna

Tranquil 2-Bedroom Apartment in Historic Bagno di Romagna
Bagno di Romagna
$204 nightly
The price is $204
Oct 20 - Oct 21
Total with taxes and fees
Tranquil 2-Bedroom Apartment in Historic Bagno di Romagna
A stone building with a wooden door, surrounded by lush greenery and a clear sky.

16. farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp

farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp
arezzo
10.0 out of 10, Exceptional, (1 review)
"Immerso nella natura con alloggio spazioso e completo di tutto. Perfetta organizzione e comunicazione da parte di Francesco chi ci ha dato anche utili consigli sul da farsi e vedere nei paraggi. Consigliato!"
Italy
Riccardo B.
$243 nightly
The price is $243
Oct 20 - Oct 21
Total with taxes and fees
farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp
Bathroom

17. Apartment in the Historic Village of Verucchio

Apartment in the Historic Village of Verucchio
Verucchio
$284 nightly
The price is $296
Oct 20 - Oct 21
Total with taxes and fees
Apartment in the Historic Village of Verucchio
A multi-story hotel with a swimming pool, outdoor seating, and palm trees.

18. Nero D'Avorio Aparthotel & SPA

Nero D'Avorio Aparthotel & SPA
Rimini
8.8 out of 10, Excellent, (79 reviews)
"Very nice close to airport."
United Kingdom
Julie
$68 nightly
The price is $79
Oct 20 - Oct 21
Total with taxes and fees
Nero D'Avorio Aparthotel & SPA
A living room with a staircase, a kitchen area, and a door leading outside.

19. La Nocina

La Nocina
Santa Sofia
$175 nightly
The price is $192
Oct 20 - Oct 21
Total with taxes and fees
La Nocina
A wooden deck with a pool, two umbrellas, and lounge chairs.

20. Riflessi di Lago – Agriturismo with Experiences, Breakfast Included - Le Ceregne Bio

Riflessi di Lago – Agriturismo with Experiences, Breakfast Included - Le Ceregne Bio
Pieve Santo Stefano
$321 nightly
The price is $321
Oct 24 - Oct 25
Total with taxes and fees
Riflessi di Lago – Agriturismo with Experiences, Breakfast Included - Le Ceregne Bio
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 Pennabilli Hotel Reviews

Hotel De Londres

Hotel De Londres

10/10 Excellent
"Nice hotel, small but clean room nice bed and plentiful breakfast. Will be back"
Giovanni 3-night trip
Posted 1 day ago
Hotel De Londres

Find out more about Pennabilli

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

Pennabilli vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pennabilli. 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 Pennabilli 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 $79 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 Pennabilli rentals

At Expedia, we put the best Pennabilli 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 Pennabilli 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 Pennabilli 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 Pennabilli. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Pennabilli?

Yes, there are vacation rentals in Pennabilli close to Orto dei Frutti Dimenticati, or you can choose a more secluded option if you want a relaxing stay. Pennabilli is known for its cathedral and seaside. Make sure you have time to check out the art and temples during your trip.

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

Stunning, historic 18c Farmhouse - with Private Pool (sleeps 12-13): This vacation home rental outside Pennabilli is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Pennabilli?

Choose from 3 Expedia vacation rentals in Pennabilli for a memorable vacation.

What’s there to see and do in Pennabilli?

Orto dei Frutti Dimenticati and Valle del Marecchia are a couple of scenic spots to enjoy the outdoors, whereas Mateureka Museum of Calculation is one of the cultural attractions. Porta San Francesco and Chiesa del Santuario della Madonna delle Grazie are a couple of places you'll find in the larger area.

What’s a vacation rental in Pennabilli like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Pennabilli. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family trips.