San Leo Vacations from $801

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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.
Grand Hotel Elite

Grand Hotel Elite

4 out of 5
Saragozza-Porto
Price was $953, price is now $801 per person
$801
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bologna (BLQ)
7/10 Good! (94 reviews)
Very clean, spacious room. Nice breakfast, with a lot of choice. Easily reached by bus Q from the airport

Reviewed on Aug 19, 2025

UNA Hotels Bologna Centro

UNA Hotels Bologna Centro

4 out of 5
Historic Center
Price was $1,155, price is now $947 per person
$947
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bologna (BLQ)
8.8/10 Excellent! (1,008 reviews)
When we went to shower, the tub was backing up with yellow water and floating debris. Since we were already late to our show,we now had to leave without taking a shower .This small studio room was over $600.00 per night ! After complaining to the staff, we were left 2 cocktail vouchers . As it was , I was paying for 3 nights and only staying two. I think they should have done a bit more .

Reviewed on Sep 26, 2025

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

5 out of 5
Historic Center
Save 100% on your flight
Price was $2,533, price is now $2,081 per person
$2,081
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bologna (BLQ)
9.6/10 Exceptional! (634 reviews)
Beautiful hotel with every amenity. Wonderful staff and perfect location

Reviewed on Oct 3, 2025

Elizabeth Lifestyle Hotel

Elizabeth Lifestyle Hotel

4 out of 5
Bologna Fiere District
Price was $1,085, price is now $911 per person
$911
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bologna (BLQ)
9/10 Wonderful! (431 reviews)
Did not like that the Refrigerator was being used for a mini bar. Did not like that we had to pay for parking. Did not like that we had to ask for ice. Bed was rock hard. Breakfast was great however the available coffee sucked. We were not aware that we could ask for cappuccino or fresh brewed coffee.

Reviewed on Sep 10, 2025

Albergo Rossini 1936 Small & Charming

Albergo Rossini 1936 Small & Charming

4.5 out of 5
Historic Center
Price was $1,333, price is now $1,127 per person
$1,127
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bologna (BLQ)
8.8/10 Excellent! (113 reviews)
Staff was super friendly. Room was clean and quiet. Breakfast was great!

Reviewed on Oct 4, 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

Rimini: San Valentino Vineyards Tour with DOC Wine Tastings

Rimini: San Valentino DOC Wine Tastings

$38
per adult
Rimini: San Valentino DOC Wine Tastings
San Marino: Titanus Museum Multimedia Experience

San Marino: Titanus Museum Multimedia Experience

$9
per adult
San Marino: Titanus Museum Multimedia Experience
Tasting of the Romagna tradition in the heart of San Marino

Tasting of the Romagna tradition in the heart of San Marino

$65
per adult
Tasting of the Romagna tradition in the heart of San Marino
See all activities in San Leo

San Leo Hotel Deals

Club Meeting Hotel

Club Meeting Hotel

4 out of 5
Via Regina Elena 171, Rimini, RN
$119 nightly
The price is $141 total per night from Oct 9 to Oct 10
$141 total
Oct 9 - Oct 10
Total with taxes and fees
8/10 Very Good! (170 reviews)
"Was not happy with the staff"

Reviewed on Jul 28, 2025

Club Meeting Hotel
hotel half moon restaurant

hotel half moon restaurant

Viale Brindisi 18, Rimini, RN
8/10 Very Good! (75 reviews)
"This hotel is a great value and perfect location. Staff was friendly too. The one massive drawback is the club next door will be blasting music until 5am every night. I hardly got any sleep in Rimini as a result but overall still give this place a big thumbs up and it’s not their fault the club next ..."

Reviewed on Oct 2, 2025

Get rates
hotel half moon restaurant
Hotel Card International

Hotel Card International

4 out of 5
Via Dante Alighieri 50, Rimini, RN
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $69 total per night from Oct 12 to Oct 13
$69 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (106 reviews)
"Good location, small but clean. Friendly staff."

Reviewed on Sep 26, 2025

Hotel Card International
See all 2,730 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.

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 $801 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.

Explore a world of travel with Expedia

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.