San Leo Vacations from $716

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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.
UNA Hotels Bologna Centro

UNA Hotels Bologna Centro

4 out of 5
Historic Center
Price was $864, price is now $716 per person
$716
per person
Mar 31 - Apr 4
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Bologna (BLQ)
8.8/10 Excellent! (999 reviews)
Clean spacious room. Friendly staff. Convenient location near central train station.

Reviewed on Dec 20, 2025

Phi Hotel Bologna

Phi Hotel Bologna

4.5 out of 5
Historic Center
Price was $1,177, price is now $957 per person
$957
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Bologna (BLQ)
9.4/10 Exceptional! (1,002 reviews)
Fantastic location. Fantastic room and comfy bed. Breakfast

Reviewed on Dec 15, 2025

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

5 out of 5
Historic Center
Price was $2,410, price is now $1,986 per person
$1,986
per person
Mar 31 - Apr 4
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Bologna (BLQ)
9.6/10 Exceptional! (640 reviews)
Beautiful hotel with every amenity. Wonderful staff and perfect location

Reviewed on Oct 3, 2025

Smy Bologna Centrale

Smy Bologna Centrale

4 out of 5
Santo Stefano
Price was $960, price is now $795 per person
$795
per person
Mar 31 - Apr 4
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Bologna (BLQ)
7.6/10 Good! (472 reviews)
Good position, close to station and downtown. Clean, quiet and regular price

Reviewed on Sep 3, 2025

The Social Hub Bologna

The Social Hub Bologna

4 out of 5
Bologna Fiere District
Price was $919, price is now $772 per person
$772
per person
Feb 13 - Feb 18
found 18 hours ago
Roundtrip flight included
Detroit (DTW) to Bologna (BLQ)
9/10 Wonderful! (634 reviews)
Loved this place. Easy, clean, close to airport.

Reviewed on Jan 7, 2026

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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

Rimini: San Valentino Vineyards Tour with DOC Wine Tastings

Rimini: San Valentino DOC Wine Tastings

$38
per adult
Rimini: San Valentino DOC Wine Tastings
Entrance Ticket - Titanus Museum: Multimedia Experience

Entrance Ticket - Titanus Museum: Multimedia Experience

$7
per adult
Entrance Ticket - Titanus Museum: Multimedia Experience
See all activities in San Leo

San Leo Hotel Deals

Hotel Aria

Hotel Aria

4.5 out of 5
Viale Dandolo, 13 Rimini RN
$81 nightly
The price is $98 total per night from Jan 24 to Jan 25
$98 total
Jan 24 - Jan 25
Total with taxes and fees
9.4/10 Exceptional! (430 reviews)
Great location, wonderful breakfast

Reviewed on Oct 28, 2025

Hotel Aria
Savoia Hotel Rimini

Savoia Hotel Rimini

4.5 out of 5
Viale Lungomare Murri 13 Rimini RN
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $123 total per night from Feb 9 to Feb 10
$123 total
Feb 9 - Feb 10
Total with taxes and fees
8.6/10 Excellent! (555 reviews)
Always a pleasure to be back at Savoia Hotel. Every time I go to Rimini I feel

Reviewed on Jan 5, 2026

Savoia Hotel Rimini
Hotel De Londres

Hotel De Londres

4 out of 5
Viale Vespucci 24 Rimini RN
$84 nightly
The price is $102 total per night from Jan 22 to Jan 23
$102 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (463 reviews)
Amazing under all aspects.

Reviewed on Nov 15, 2025

Hotel De Londres
See all 2,658 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 $716 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.

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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.