Pennabilli Vacations from $910

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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.
Borgo Tre Vaselle

Borgo Tre Vaselle

5 out of 5
Price was $974, price is now $910 per person
$910
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Ancona (AOI)
10/10 Exceptional! (4 reviews)
Amazing spot! Much better than the pictures. Amazing food, quiet and relaxing place.

Reviewed on Oct 9, 2026

Bleis Hotel

Bleis Hotel

4 out of 5
Bologna Fiere District
Price was $1,122, price is now $1,029 per person
$1,029
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Bologna (BLQ)
8.6/10 Excellent! (519 reviews)
The staff at the hotel were all very courteous and helpful. The bedroom was well-appointed and spotlessly clean. The location of the hotel is not great as there is absolutely nothing around it. It is well connected to Bologna via bus (about 25/30 mins from the centre) which as advertised does stop immediately outside the premises. We had hoped to have dinner on the Sunday evening as we had a very early flight on the Monday morning. Unfortunately the restaurant was closed on Sunday despite being advertised as open 7 days which was disappointing. There wasn’t much activity in the hotel and the bar area wasn’t staffed as such and was a bit soulless and uninspiring. The cost of the hotel was much the same as others which had more amenities around them.

Reviewed on Sep 28, 2026

Phi Hotel Bologna

Phi Hotel Bologna

4.5 out of 5
Historic Center
Price was $1,251, price is now $1,153 per person
$1,153
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Bologna (BLQ)
9.4/10 Exceptional! (1,003 reviews)
This was my second stay at Hotel Phi. The location cannot be beat! I stayed in one of the apartments and it was an excellent experience - the kitchen was well-appointed for basic needs during my stay and the staff was immediately responsive to a small issue with the hot water one morning. I will definitely plan to stay here again during my next visit to Bologna.

Reviewed on Oct 21, 2026

Touring Hotel

Touring Hotel

4 out of 5
Historic Center
Price was $1,295, price is now $1,206 per person
$1,206
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Bologna (BLQ)
9/10 Wonderful! (774 reviews)

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

5 out of 5
Historic Center
Price was $2,355, price is now $2,208 per person
$2,208
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Bologna (BLQ)
9.6/10 Exceptional! (676 reviews)

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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.
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What to do in Pennabilli

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
Cook Like a Local in San Marino Countryside

Cook Like a Local in San Marino Countryside

$111
per adult
Cook Like a Local in San Marino Countryside
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

3 out of 5
Viale Vespucci 46 Rimini RN
$39 nightly
The price is $49 total per night from Nov 28 to Nov 29
$49 total
Nov 28 - Nov 29
Total with taxes and fees
8.6/10 Excellent! (233 reviews)
"Pillows should be changed … unusable … too hard"

Reviewed on Oct 16, 2026

Hotel Corallo Rimini
Hotel Royal Plaza

Hotel Royal Plaza

4 out of 5
Viale Trieste 22 Rimini RN
$25 nightly
The price is $37 total per night from Nov 9 to Nov 10
$37 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (133 reviews)
"Lovely hotel located near the town and beach. We were allowed to check in early, which was a great help. Staff were friendly and welcoming. Hotel was clean and and we loved the use of the pool. Breakfast was good with a a mixture of decent items to choose from. Would definitely recommend this ..."

Reviewed on Oct 16, 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
$51 nightly
The price is $65 total per night from Nov 10 to Nov 11
$65 total
Nov 10 - Nov 11
Total with taxes and fees
8.6/10 Excellent! (559 reviews)
"Well located near the beach and a 20 min walk to the railway station. Nice and clean, decent room, good breakfast, would definitely stay again..."

Reviewed on Oct 26, 2026

Hotel Polo
See all 2,425 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 $910 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.