Fairlee Vacations from $760

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Your Fairlee Vacation

When a city escape is calling, answer it with a vacation package to Fairlee. With all your travel arrangements in order before you go, all you need to do here is concentrate on having a blast. Every trip to Fairlee needs a well-planned itinerary. Fill yours with leading attractions like Washington College, Garfield Center for the Arts at the Prince Theater and River Arts Chestertown. Whoever you're heading away with and whatever your budget, your ultimate Fairlee vacation is only clicks away with Expedia.

The Latest Fairlee vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Gold Coast

Comfort Inn Gold Coast

2.5 out of 5
North Ocean City
Price was $890, price is now $760 per person
$760
per person
May 11 - May 17
found 23 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.4/10 Very Good! (1,000 reviews)
Clean room. Quiet. Lots of parking

Reviewed on Feb 28, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,199, price is now $922 per person
$922
per person
May 11 - May 17
found 23 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (720 reviews)
Very clean, updated, with friendly staff.

Reviewed on Mar 6, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $1,031, price is now $820 per person
$820
per person
May 11 - May 17
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.6/10 Excellent! (1,154 reviews)
Love the ocean front rooms nice size balcony, best if you can get a end room, more windows

Reviewed on Mar 4, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,160, price is now $924 per person
$924
per person
May 11 - May 17
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9/10 Wonderful! (3,444 reviews)
Room was clean, comfortable, 11th floor was a little bit too high for me. Next trip lower floor. Friendly staff

Reviewed on Feb 28, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,273, price is now $1,066 per person
$1,066
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
7.4/10 Good! (171 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.

Reviewed on Oct 1, 2025

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Discover the most popular places to visit in Fairlee

Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.

Washington College

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

Fairlee Hotel Deals

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Mar 12 to Mar 13
$113 total
Mar 12 - Mar 13
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Great experience.

Reviewed on Feb 18, 2026

Hilton Garden Inn Baltimore/White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 out of 5
2110 Emmorton Park Rd Edgewood MD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $91 total per night from Mar 12 to Mar 13
$91 total
Mar 12 - Mar 13
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Friendly staff...nice room

Reviewed on Mar 5, 2026

Hampton Inn & Suites Edgewood/Aberdeen-South
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

3 out of 5
8477 Cordon Way Baltimore MD
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $117 total per night from Mar 15 to Mar 16
$117 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
Clean room and helpful staff

Reviewed on Mar 6, 2026

Fairfield Inn & Suites by Marriott White Marsh
See all 346 properties in Fairlee
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 Fairlee Vacation Packages

Fairlee Essential Information

Language
English
Currency
U.S dollars
Top Sights
Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College

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Frequently asked questions

How much does a Fairlee vacation package cost?
Offering great value package deals from $760 on Expedia, you'll be pleasantly surprised at how much a vacation to Fairlee costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Fairlee?
You can typically find lower prices and better availability in September, November and December. Browse our cheap Fairlee vacation packages and you could land some great off-season deals.
How many days is enough for Fairlee?
The ideal length of your Fairlee vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to check out all the top attractions and discover some hidden treasures along the way.
How to find the best Fairlee package deals?
Use Expedia's handy filters to find some fabulous Fairlee package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Fairlee package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Fairlee vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Fairlee trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Fairlee?
If you're planning an impromptu Fairlee getaway, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Fairlee vacation packages?
Secure your dream escape to Fairlee with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.