San Leo Vacations from $1,058

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Your San Leo Vacation

Let our vacation packages to San Leo inspire your next getaway. There's loads to like about this interesting city, starting with the neighborhood of Montegrimano, which is good for nature and views. Eager to start exploring your surroundings? Fortress of San Leo, Montebello Castle and Rocca del Sasso are some of the best places to visit during your trip to San Leo. Browse Expedia's extensive range of travel options and start organizing your ideal vacation to San Leo today.

The Latest San Leo vacation packages

Price found within the past 48 hours. Click for updated prices.
Living Place Hotel

Living Place Hotel

4 out of 5
San Donato-San Vitale
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Bologna (BLQ)
8.2/10 Very Good! (729 reviews)
Living Place hotel was clean and quiet!

Reviewed on Jun 30, 2025

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

5 out of 5
Historic Center
per person
Sep 6 - Sep 9
found 24 hours ago
Roundtrip flight included
St. Louis (STL) to Bologna (BLQ)
9.6/10 Exceptional! (619 reviews)
Lovely historical hotel. Great location! Very friendly and helpful staff.

Reviewed on Jul 3, 2025

Astoria Suite Hotel

Astoria Suite Hotel

4 out of 5
Marina Centro
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bologna (BLQ)
8.8/10 Excellent! (224 reviews)
Italy vacation; stayed a few days in Rimini at the Astoria Suite Hotel. Great staff, Front Desk, Bar, Restaurant, Housekeeping, everyone were super helpful and friendly. Great hotel near beach (literally a 1/2 block walk). Close to everything. If we find our way back to Rimini, we will be staying at the Astoria Suite Hotel. Thanks

Reviewed on Jul 14, 2023

Hotel Il Guercino

Hotel Il Guercino

4 out of 5
Bologna Fiere District
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Bologna (BLQ)
8.6/10 Excellent! (1,000 reviews)
Closer to centre than I thought as don’t usually stay on that side of railway. It was a blessing as there was roadworks outside one hotel and work on the towers at another. Room nice but plain, bathroom very good. Quick check in and room available early. Staff very helpful.

Reviewed on Jul 1, 2025

Hotel Porta San Mamolo

Hotel Porta San Mamolo

4 out of 5
Historic Center
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Bologna (BLQ)
9.2/10 Wonderful! (732 reviews)
We loved the location and our stay!

Reviewed on Jul 1, 2025

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Discover the most popular places to visit in San Leo

Fortress of San Leo

Fortress of San Leo

Learn about the local history of San Leo when you take a trip to Fortress of San Leo. Discover the mountain views while you're in the area.

Fortress of San Leo

Cathedral of San Leo

You can learn about the history of San Leo with a stop at Cathedral of San Leo. Discover the mountain views while you're in the area.

Cathedral of San Leo

What to do in San Leo

San Leo Cashmere: Farm Experience

San Leo Cashmere: Farm Experience

$56
per adult
San Leo Cashmere: Farm Experience
FORTRESS AT SUNSET

San Leo: Entrance ticket to the fortress and prison of Cagliostro

$13
per adult
San Leo: Entrance ticket to the fortress and prison of Cagliostro
See all activities in San Leo

San Leo Hotel Deals

c-hotels International
c-hotels International
3 out of 5
Viale Modena 19, Cattolica, RN
Fully refundableReserve now, pay when you stay
$43 nightly
The price is $52 total per night from Jul 8 to Jul 9
$52 total
Jul 8 - Jul 9
Total includes taxes and fees
8.2/10 Very Good! (81 reviews)
Lovely, Clean Hotel
"This hotel is a great find, it's well priced, great location and it is IMMACULATE, fresh towels everyday, bed made and room cleaned everyday. Staff were very friendly and accommodating, I would definitely return here! You get what you pay for in most places, however this hotel exceeded my expectations ..."

Reviewed on Jun 25, 2025

c-hotels International
HOTEL YOUNG PEOPLE UNDER 40
HOTEL YOUNG PEOPLE UNDER 40
Viale Regina Elena 253, Rimini, RN
$41 nightly
The price is $51 total per night from Jul 7 to Jul 8
$51 total
Jul 7 - Jul 8
Total includes taxes and fees
6/10 (8 reviews)
"Grazie molto"

Reviewed on Jun 15, 2025

HOTEL YOUNG PEOPLE UNDER 40
Hotel Radar
Hotel Radar
3 out of 5
Viale Giuseppe Giusti, 4, Rimini, RN
$48 nightly
The price is $59 total per night from Jul 7 to Jul 8
$59 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (135 reviews)
"Right next to the beach, perfect for a small getaway"

Reviewed on Jun 28, 2025

Hotel Radar
See all 2,742 properties in San Leo
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 San Leo Vacation Packages

San Leo Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Federico Fellini Intl. Airport (RMI)
Population
200
Max Temp Winter
50ºF
Max Temp Summer
80ºF
Top Sights
Montebello Castle, Skypark Parco Avventura and Grotte di Onferno

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Frequently asked questions

How much does a San Leo vacation package cost?
You'll find cheap prices from $1,058 on Expedia for your San Leo escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to San Leo costs.
What are the cheapest months to go to San Leo?
You're likely to find reduced prices and greater availability in November, December and January. Explore our cheap San Leo vacation packages and you could land some excellent off-season deals.
How many days is enough for San Leo?
With a well-organized travel plan, you can easily tick off the top San Leo sights in a few days. But if you'd like to discover hidden spots or go on day tours, think about booking your San Leo vacation for longer.
Is it worth booking a vacation package to San Leo?
San Leo is a good vacation destination with attractions like Fortress of San Leo among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a San Leo vacation promises a good time for everyone.
How to find the best San Leo package deals?
Start your search for a San Leo package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal San Leo package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your San Leo adventure underway.
Is it cheaper to book a San Leo vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your San Leo trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to San Leo?
If you're considering a spontaneous San Leo adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to San Leo?

  1. Choose when to get away: Check your diary and get your bags packed. Your favorite season and the activities on offer will also help you decide when to escape to San Leo.
  2. Plan your budget wisely: Besides the price of your hotel, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could crop up during your trip to San Leo.
  3. Explore San Leo using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to San Leo. You can also save your favorite locations, collaborate with family and friends and manage all your plans in one place.
  4. Decide how many days away: Start by making a list of all the activities and attractions you'd like to get to in San Leo. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a San Leo vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of San Leo. Find all the fun things to do in San Leo with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later San Leo vacation packages?
Your San Leo getaway is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.