Fairlee Vacations from $412

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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.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was $550, price is now $412 per person
$412
per person
Oct 2 - Oct 6
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Salisbury (SBY)
9.8/10 Exceptional! (278 reviews)
A great location for this beachy vibe motel. A couple things I would suggest to the property manager would be to offer a coffee cart each morning, add an additional chair and bedside table to the room and finally, I would suggest that the room be serviced automatically if you’re there for 4 nights…we didn’t get our room serviced our entire time. Beyond those minor things, it was a quirky, clean, convenient motel that has 95% of the components needed for a top-notch beach motel.

Reviewed on Aug 24, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,506, price is now $1,162 per person
$1,162
per person
Oct 2 - Oct 6
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,117 reviews)
I would recommend any family that's looking for a vacation just stay at the Grand to comfortability the beautiful sight and everyone at the hotel is so friendly

Reviewed on Aug 26, 2025

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

2.5 out of 5
Downtown Ocean City
Price was $1,519, price is now $1,185 per person
$1,185
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9/10 Wonderful! (1,005 reviews)
Nice in the beach get what you pay for

Reviewed on Aug 26, 2025

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk

2.5 out of 5
Downtown Ocean City
Price was $2,700, price is now $2,111 per person
$2,111
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
9/10 Wonderful! (1,010 reviews)
Very nice and efficient staff

Reviewed on Aug 24, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $1,332, price is now $1,051 per person
$1,051
per person
Oct 2 - Oct 6
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (81 reviews)
Will definitely stay again!

Reviewed on Aug 25, 2025

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Discover the most popular places to visit in Fairlee

Washington College

4/5(13 reviews)

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

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

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
$102 nightly
The price is $117 total per night from Aug 31 to Sep 1
$117 total
Aug 31 - Sep 1
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"Nice clean hotel with very friendly staff"

Reviewed on Aug 24, 2025

Hilton Garden Inn Baltimore/White Marsh
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $64 total per night from Sep 16 to Sep 17
$64 total
Sep 16 - Sep 17
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
"Room was very clean and smelled great as well, the hallways getting to room are a little rough. Ice machine on my floor was out of order but the one on 1st floor was working. They have a coin laundry and pool neither one i used but were available. And breakfast from 6-9"

Reviewed on Aug 21, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
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
$88 nightly
The price is $99 total per night from Sep 1 to Sep 2
$99 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"We have stayed here many times as our family lives in the area! Its a great place"

Reviewed on Aug 24, 2025

Hampton Inn & Suites Edgewood/Aberdeen-South
See all 339 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.

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Frequently asked questions

How much does a Fairlee vacation package cost?
Offering great value package deals from $412 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.