San Leo Vacation Packages

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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.

Top San Leo Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Borgo Tre Vaselle

Borgo Tre Vaselle

5 out of 5
Price was CA $2,032, price is now CA $1,676 per person
CA $1,676
per person
Dec 15 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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

Grand Hotel Majestic già Baglioni

Grand Hotel Majestic già Baglioni

5 out of 5
Historic Center
Price was CA $5,229, price is now CA $4,589 per person
CA $4,589
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Bologna (BLQ)
9.6/10 Exceptional! (676 reviews)

Hotel Rua Frati 48 in San Francesco

Hotel Rua Frati 48 in San Francesco

5 out of 5
Old Town Modena
Price was CA $3,991, price is now CA $3,510 per person
CA $3,510
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Bologna (BLQ)
9.8/10 Exceptional! (81 reviews)
Great place . Clean room, nice staff,

Reviewed on Nov 12, 2026

Royal Hotel Carlton

Royal Hotel Carlton

4 out of 5
Historic Center
Price was CA $2,433, price is now CA $2,214 per person
CA $2,214
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Bologna (BLQ)
9.2/10 Wonderful! (1,252 reviews)

Palazzo di Varignana Resort & SPA

Palazzo di Varignana Resort & SPA

4.5 out of 5
Price was CA $3,082, price is now CA $2,858 per person
CA $2,858
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Bologna (BLQ)
9.2/10 Wonderful! (336 reviews)
This was a great place. The grounds were very beautiful.

Reviewed on Oct 4, 2026

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San Leo Hotel Deals

Hotel Corallo Rimini

Hotel Corallo Rimini

3 out of 5
Viale Vespucci 46 Rimini RN
The price is CA $44 per night from Dec 15 to Dec 16
CA $44
CA $57 total
Dec 15 - Dec 16
includes taxes & fees
8.6/10 Excellent! (234 reviews)
"Great area right on the beach with tonnes of dining options everywhere you look. Parking was safe and secure at a reasonable fee and the staff are great. Clean rooms, great showers, we wished we were staying longer."

Reviewed on Oct 31, 2026

Hotel Corallo Rimini
Hotel Royal Plaza

Hotel Royal Plaza

4 out of 5
Viale Trieste 22 Rimini RN
The price is CA $36 per night from Dec 9 to Dec 10
CA $36
CA $52 total
Dec 9 - Dec 10
includes taxes & fees
8/10 Very good! (136 reviews)
"Was a great place to stop over on the way somewhere else! Very helpful staff too!"

Reviewed on Nov 8, 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
The price is CA $83 per night from Dec 10 to Dec 11
CA $83
CA $104 total
Dec 10 - Dec 11
includes taxes & fees
Hotel Polo
See all 2,960 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular San Leo attractions

Fortress of San Leo

10.0/10 (4 reviews)
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.
See properties

What to do in San Leo

San Leo: Fortress Entry Ticket

San Leo: Fortress Entry Ticket

CA $25
per adult
San Leo: Fortress Entry Ticket
FORTRESS AT SUNSET

San Leo : Entrance Ticket to the Fortress and Cagliostro’s Prison

CA $18
per adult
San Leo : Entrance Ticket to the Fortress and Cagliostro’s Prison
Entrance Ticket - Titanus Museum: Multimedia Experience

Entrance Ticket - Titanus Museum: Multimedia Experience

CA $10
per adult
Entrance Ticket - Titanus Museum: Multimedia Experience
See all activities in San Leo

Frequently asked questions

How much does a San Leo vacation package cost?
You'll find cheap prices from CA $1,676 on Expedia for your San Leo break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to San Leo costs.
What are the cheapest months to go to San Leo?
Plan your trip for the off-peak season and you're likely to find cheap San Leo vacation packages. Keep in mind that public holidays and local festivals and events can impact prices, so do your research before you go.
How many days is enough for San Leo?
With a well-organized itinerary, you can easily tick off the top San Leo sights in a handful of days. But if you prefer 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 has everything you need for an amazing trip. Get your San Leo vacation off to a flying start by exploring major attractions like Cathedral of San Leo.
How to find the best San Leo package deals?
Begin your search for a San Leo package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect San Leo package deal right away, simply change 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 off to a flying start.
Is it cheaper to book a San Leo vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your San Leo escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to San Leo?
Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu San Leo break.
How to plan a trip to San Leo?

  1. Pick your dates: The things you'd like to do in San Leo and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to San Leo.
  3. Decide how long to go for: Now that you're more familiar with San Leo, you can figure out the ideal length of your vacation. Create a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored San Leo vacation package.

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