Pennabilli Vacations from $372

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Your Pennabilli Vacation

Reserve a Pennabilli vacation 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 vacation is just clicks away. Explore flights, hotels and more on Expedia for a getaway that's tailored just for you.

The Latest Pennabilli vacation packages

Price found within the past 48 hours. Click for updated prices.
Natural Village Resort

Natural Village Resort

$372
per person
Sep 14 - Sep 16
found 1 day ago
Roundtrip flight included
Barcelona (BCN) to Ancona (AOI)
8.4/10 Very Good! (122 reviews)
I can't speak highly enough of our trip to this resort. It really is a small village that has all the amenities you need. It is very family-focused where I would think most, if not all guests were families with young / teen children. It is pet-friendly, plenty of guests with their dogs which was lovely to see. The staff were remarkable, helpful everywhere we went and serviced us with care. The place has a great community pool, fit for all ages, has a shallow end for the little ones, a medium bit for older kids, and a deep-end for the stronger swimmers. They have a private beach area, already setup with chairs and umbrellas. There's staff on the beach as well to assist. On the beach is a seaside restaurant. Reservations are required but it was lovely sitting on the patio, overlooking the sea. The cottages themselves fit our needs. We are a family of 5 so we got the two bedroom. A little kitchen, dining area (although we had most meals outside on the porch), master bedroom for the parents, one bedroom with two beds, and a bed in the lounge. Bathroom was nice and modern. There was always entertainment happening throughout the day and evening which was included. There are small shops and restaurants that come with an extra cost but you also have the option to go off resort to shop or eat as long as you have a vehicle.

Reviewed on Jul 19, 2026

 Phi Hotel Bologna

Phi Hotel Bologna

Historic Center
$822
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
London (LON) to Bologna (BLQ)
9.4/10 Exceptional! (1,005 reviews)
Location was great. Breakfast was mediocre which is fine. Coffee was horrible.

Reviewed on Aug 5, 2026

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

Historic Center
$3,748
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bologna (BLQ)
9.6/10 Exceptional! (668 reviews)
Hotel Classensis

Hotel Classensis

$509
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
London (LON) to Bologna (BLQ)
9/10 Wonderful! (139 reviews)
Royal Hotel Carlton

Royal Hotel Carlton

Historic Center
$1,447
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bologna (BLQ)
9.2/10 Wonderful! (1,083 reviews)
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Stay near popular Pennabilli attractions

Mateureka Museum of Calculation

You can browse the exhibits at Mateureka Museum of Calculation, a museum with a story of its own, during your trip to Pennabilli. Amble around the area's seaside or visit its cathedral.
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Porta San Francesco

You can find out about the history of Pennabilli when you stop by Porta San Francesco. Take in the art scene and mountain views in the area.
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Chiesa del Santuario della Madonna delle Grazie

Chiesa del Santuario della Madonna delle Grazie is just one of the places to see in Pennabilli, so why not enjoy the other things to explore during your travels? Discover the mountain views while you're in the area.
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Valle del Marecchia

Commune with nature and explore the great outdoors at Valle del Marecchia during your travels in Pennabilli. Wander the seaside or discover the area's mountain views.
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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.
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What to do in Pennabilli

Entrance Ticket - Titanus Museum: Multimedia Experience

Entrance Ticket - Titanus Museum: Multimedia Experience

$7
per adult
Entrance Ticket - Titanus Museum: Multimedia Experience
FORTRESS AT SUNSET

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

$13
per adult
San Leo : Entrance Ticket to the Fortress and Cagliostro’s Prison
San Marino: Hands-on cooking class in the countryside

San Marino: Hands-on cooking class in the countryside

$111
per adult
San Marino: Hands-on cooking class in the countryside
See all activities in Pennabilli

Pennabilli Hotel Deals

Hotel Corallo Rimini

Hotel Corallo Rimini

Viale Vespucci 46 Rimini RN
$50 nightly
$61 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (206 reviews)
"I've been to Rimini many times, this is one of the best hotels i've stayed at. The girl at the front counter was super nice and helpful with everything we needed and advice. Easy access to beach and local businesses. Swimming pool was at the PERFECT temperature to cool the body down from the august ..."

Reviewed on Aug 6, 2026

Hotel Corallo Rimini
Hotel Avana Mare

Hotel Avana Mare

Viale Gaetano Genghini Rimini RN
$23 nightly
$31 total
Sep 7 - Sep 8
Total with taxes and fees
8/10 Very Good! (145 reviews)
"great staff and location"

Reviewed on Jul 8, 2026

Hotel Avana Mare
Grand Hotel Rimini

Grand Hotel Rimini

Parco Federico Fellini Rimini RN
$256 nightly
$293 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (356 reviews)
"Our 4 day stay was pleasant . The staff is friendly but slow at times , more at the restaurant when ordering . The rooms are nice and clean , but the beds are a bit uncomfortable and room needs to be cooler."

Reviewed on Aug 6, 2026

Grand Hotel Rimini
See all 2,437 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.

Find the Best Pennabilli Vacation Packages

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
50ºF
Max Temp Summer
80ºF
Top Sights
Montebello Castle, Skypark Parco Avventura and Cathedral of San Leo

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Frequently asked questions

How much does a Pennabilli vacation package cost?
You'll find cheap prices from $372 on Expedia for your Pennabilli escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Pennabilli costs.
What are the cheapest months to go to Pennabilli?
You can typically find lower rates and greater availability in November, December and January. Browse our cheap Pennabilli vacation packages and you could get some excellent off-season deals.
How many days is enough for Pennabilli?
You can see all the major attractions in Pennabilli within a few days, including the popular Chiesa del Santuario della Madonna delle Grazie. If you're looking for a longer Pennabilli vacation, look at which kind of activities and excursions are available in the area.
Is it worth booking a vacation package to Pennabilli?
It's no wonder a Pennabilli vacation is on the to-do list of many travelers. Leading attractions like Valle del Marecchia are just the start of things to keep you busy here.
How to find the best Pennabilli package deals?
Start your search for a Pennabilli package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Pennabilli package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pennabilli adventure off to a flying start.
Is it cheaper to book a Pennabilli vacation as a package?
You can enjoy significant savings on your next Pennabilli getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pennabilli?
If you have your Pennabilli vacation dates locked in, book as soon as you can to grab some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Pennabilli?
  1. Choose when to travel: Check your calendar and pack your bags. Your favorite season and the available activities will also help you decide when to visit Pennabilli.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to save for your trip to Pennabilli. Then, select a hotel that matches your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Use Expedia's trip planning tool to discover Pennabilli: Research every aspect of your trip to Pennabilli with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the activities and sights you want to experience in Pennabilli. Then, estimate how long you'll need for each, including any travel time.
  5. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the perfect Pennabilli vacation package for you.
  6. Book any activities or excursions: Here's the fun part — organizing everything you want to do and see. Check out some of the exciting things to do in Pennabilli and book your tickets in advance to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Pennabilli vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Pennabilli trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.