Pennabilli Holidays from £184

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Pennabilli Holiday

Reserve a Pennabilli holiday package and focus on what counts — enjoying yourself. No more planning hassles, just more time to experience the best of this lively city, such as its medieval heritage and spectacular views. Make your trip to Pennabilli even more enjoyable by going sightseeing. Mateureka Museum of Calculation, Orto dei Frutti Dimenticati and Chiesa del Santuario della Madonna delle Grazie are among the leading attractions you'll want to explore. That dream Pennabilli holiday is just clicks away. Explore flights, hotels and more on Expedia for a getaway that's tailored just for you.

Top Pennabilli Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Social Hub Bologna

The Social Hub Bologna

4 out of 5
Bolognina
Price was £232, price is now £184 per person
£184
per person
5 Feb - 8 Feb
found 19 hours ago
Return flight included
London (LON) to Bologna (BLQ)
9/10 Wonderful! (954 reviews)

Hotel Brun

Hotel Brun

4 out of 5
Historic Center
Price was £376, price is now £281 per person
£281
per person
5 Feb - 8 Feb
found 19 hours ago
Return flight included
London (LON) to Bologna (BLQ)
9.8/10 Exceptional! (220 reviews)
We loved our 3 night stay at Brun. The hotel is perfectly proportioned and the rooms an excellent standard. When asking for extra pillows we were met with “soft or firm?!” The location is perfectly located as a base from which to explore Bologna. But our stay was really made by the staff. Everyone from the front desk to wait staff at breakfast felt so genuine and invested their guests. We had a wonderful time, would absolutely recommend and can’t wait to return! X

Reviewed on 8 Nov 2026

Royal Hotel Carlton

Royal Hotel Carlton

4 out of 5
Historic Center
Price was £327, price is now £248 per person
£248
per person
5 Feb - 8 Feb
found 19 hours ago
Return flight included
London (LON) to Bologna (BLQ)
9.2/10 Wonderful! (1,252 reviews)

Borgo Tre Vaselle

Borgo Tre Vaselle

5 out of 5
Save 100% on your flight
Price was £940, price is now £737 per person
£737
per person
27 Dec - 2 Jan
found 20 hours ago
Return flight included
London (LON) to Ancona (AOI)
10/10 Exceptional! (4 reviews)
Amazing spot! Much better than the pictures. Amazing food, quiet and relaxing place.

Reviewed on 9 Oct 2026

Sina Brufani

Sina Brufani

5 out of 5
Old Town Perugia
Price was £930, price is now £741 per person
£741
per person
27 Dec - 2 Jan
found 20 hours ago
Return flight included
London (LON) to Ancona (AOI)
9.2/10 Wonderful! (682 reviews)

Pennabilli Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Federico Fellini Intl. Airport (RMI)
Population
980
Max Temp Winter
10ºC
Max Temp Summer
27ºC
Top Sights
Montebello Castle, Skypark Parco Avventura and Cathedral of San Leo

Top hotels in Pennabilli

Hotel Corallo Rimini

Hotel Corallo Rimini

3 out of 5
Viale Vespucci 46 Rimini RN
The price is £28 per night from 13 Dec to 14 Dec
£28
13 Dec - 14 Dec
includes taxes & fees
8.6/10 Excellent! (234 reviews)
"Great area right on the beach with tonnes of dining options everywhere you look. Parking was safe and secure at a reasonable fee and the staff are great. Clean rooms, great showers, we wished we were staying longer."

Reviewed on 31 Oct 2026

Hotel Corallo Rimini
Hotel Royal Plaza

Hotel Royal Plaza

4 out of 5
Viale Trieste 22 Rimini RN
The price is £28 per night from 22 Nov to 23 Nov
£28
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (136 reviews)
"Was a great place to stop over on the way somewhere else! Very helpful staff too!"

Reviewed on 8 Nov 2026

Hotel Royal Plaza
Hotel Polo

Hotel Polo

4 out of 5
Viale A. Vespucci, 23 Rimini RN
Fully refundableReserve now, pay when you stay
The price is £58 per night from 10 Dec to 11 Dec
£58
10 Dec - 11 Dec
includes taxes & fees
Hotel Polo
See all 2,443 properties in Pennabilli
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Pennabilli attractions

Orto dei Frutti Dimenticati

Enjoy an outing to Orto dei Frutti Dimenticati during your stay in Pennabilli. Stroll along the seaside or visit the cathedral while you're in the area.
See properties

What to do in Pennabilli

FORTRESS AT SUNSET

San Leo : Entrance Ticket to the Fortress and Cagliostro’s Prison

£10
per adult
San Leo : Entrance Ticket to the Fortress and Cagliostro’s Prison
Entrance Ticket - Titanus Museum: Multimedia Experience

Entrance Ticket - Titanus Museum: Multimedia Experience

£5
per adult
Entrance Ticket - Titanus Museum: Multimedia Experience
San Marino's Three Towers: An Audio Tour of the Ancient Republic

San Marino's Three Towers: An Audio Tour of the Ancient Republic

£4
per adult
San Marino's Three Towers: An Audio Tour of the Ancient Republic
See all activities in Pennabilli

Frequently asked questions

How much does a Pennabilli travel package cost?
The most affordable Pennabilli travel package is £184, so your dream trip can become a reality — without the high price tag. Bundle flights, hotels and car rentals to custom build a package that matches your travelling style.
If I'm not able to travel, can I cancel my Pennabilli travel package?
Because we know life can be unpredictable, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
How do I get a cheap travel package to Pennabilli?
You'll save loads of cash if you combine your flights, car rentals and hotels into a Pennabilli travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 properties all over the world, which means you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Pennabilli holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply pick the payment plan best suited to your needs during the checkout process and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If making small repayments each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday in multiple transactions.
  • Low deposit holidays: When you spot an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your getaway.

Where should I stay in Pennabilli?
With popular attractions like Orto dei Frutti Dimenticati and Valle del Marecchia in this neighbourhood, look for a hotel positioned near either of them. Chiesa del Santuario della Madonna delle Grazie is another Pennabilli sight that people flock to.
What are the top hotels in Pennabilli?
One of the most popular places to stay in Pennabilli is Hotel il Duca del Montefeltro, in the neighbourhood of Scavolino. Wander the city by day and then relax in your comfortable room after sundown.
How far in advance should I book my Pennabilli holiday?
To land cheap prices, book nice and early. Air carriers typically advertise flight tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Pennabilli, there are always lots of great deals on Expedia. Check them out now!
What does an Expedia Pennabilli travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're venturing to Pennabilli with the entire family or enjoying a solo break, there's a bundle to suit every style and budget. Once you've made your booking, why not add on some activities?
What should I know before booking a Pennabilli travel package?
You'll pick up excellent savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything together makes trip planning much easier. So why waste your time or money? Whether you're putting together a ritzy romantic getaway or an affordable family break, take a look at our package deals today.
Can I choose my airline with a Pennabilli Expedia travel package?
Most definitely. Expedia has over 550 airline partners to select from worldwide. With so many choices, finding the perfect carrier to take you to Pennabilli will be a breeze.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.