Pennabilli Vacations from $501

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

    Plan, book, and manage your trip all in one place

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.
Hotel Sant'Orsola Collection by GSA Hotels

Hotel Sant'Orsola Collection by GSA Hotels

San Donato-San Vitale
$501
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Madrid (MAD) to Bologna (BLQ)
7.4/10 Good! (18 reviews)
Nice and basic hotel in a good location

Reviewed on Sep 15, 2026

Hotel San Felice

Hotel San Felice

Historic Center
Save 100% on your flight
$576
per person
Nov 24 - Nov 30
found 12 hours ago
Roundtrip flight included
Madrid (MAD) to Bologna (BLQ)
8/10 Very Good! (188 reviews)
Good location- close to the main attractions whilst not being in the centre of it. Also only a short walk to a self se rvice laundry and a supermarket (co-op). There is also a general store next door with all sorts of handy items. There is only a short distance to transport options as well. There is general noise you hear from other rooms however not terrible. The bathroom was a reasonable size.

Reviewed on Sep 6, 2026

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

Historic Center
$2,740
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Asheville (AVL) to Bologna (BLQ)
9.6/10 Exceptional! (672 reviews)
Everything and everyone there was amazing. The ONLY thing I would suggest is that they pony up for some soft sheets and pillowcases. Shockingly stiff and uncomfortable. We resorted to wrapping our pillow with a t-shirt.

Reviewed on Aug 8, 2026

UNA Hotels Bologna Centro

UNA Hotels Bologna Centro

Historic Center
$1,387
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Asheville (AVL) to Bologna (BLQ)
8.8/10 Excellent! (1,003 reviews)
Located directly across the street from train station. Convenient. Nice modern cutting edge furnishings. Only down side was there are no walkin showers. Tub/shower combo is deep and difficult to get in/out of for older persons. EXTREME slip hazzad! Had to put towel on floor of tub so as not to slip. Very low water pressure. Restaurant has a nice buffet style breakfast.

Reviewed on Sep 20, 2026

Hotel Internazionale

Hotel Internazionale

Historic Center
$1,695
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Asheville (AVL) to Bologna (BLQ)
9/10 Wonderful! (1,015 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Pennabilli
View all trips

Stay near popular Pennabilli attractions

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.
See properties

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.
See properties

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

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.
See properties

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.
See properties

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

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

$5
per adult
San Marino's Three Towers: An Audio Tour of the Ancient Republic
See all activities in Pennabilli

Pennabilli Hotel Deals

Hotel Corallo Rimini

Hotel Corallo Rimini

Viale Vespucci 46 Rimini RN
$33 nightly
$42 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (218 reviews)
"Great location. The breakfast was fantastic. Would definitely recommend the hotel to friends."

Reviewed on Sep 20, 2026

Hotel Corallo Rimini
Hotel Avana Mare

Hotel Avana Mare

Viale Gaetano Genghini Rimini RN
Fully refundableReserve now, pay when you stay
$24 nightly
$33 total
Sep 26 - Sep 27
Total with taxes and fees
8/10 Very Good! (148 reviews)
"We chose this hotel because of the location and it's a smaller than most of the other hotels.We also loved being around the locals and away from the main street. The hotel staff were so friendly and accommodating, especially as we arrived really early for check in. The room was exactly what we wanted. ..."

Reviewed on Sep 19, 2026

Hotel Avana Mare
NAUTIC BEACH HOTEL

NAUTIC BEACH HOTEL

Viale Giuliano Dati 91 Rimini RN
Fully refundableReserve now, pay when you stay
$35 nightly
$44 total
Sep 25 - Sep 26
Total with taxes and fees
8.2/10 Very Good! (90 reviews)
"No complaints at all, great location, everythin needed was there. Breakfast was fantastic!"

Reviewed on Jul 11, 2026

NAUTIC BEACH HOTEL
See all 2,450 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

More vacations you might like

Frequently asked questions

How much does a Pennabilli vacation package cost?
You'll find cheap prices from $501 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.

Explore a world of travel with Expedia

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