Assawoman Vacations from $780

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The Latest Assawoman vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $971, price is now $780 per person
$780
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,661 reviews)
Clean place, great amenities!

Reviewed on Jul 19, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,084, price is now $838 per person
$838
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
8.2/10 Very Good! (749 reviews)
The younger girl at the front desk was very helpful and friendly. It was to be welcomed by someone so pleasant and friendly. The ocean front rooms are spacious with nice balconies overlooking the boardwalk and the beach.

Reviewed on Jul 16, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $959, price is now $782 per person
$782
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8/10 Very Good! (38 reviews)
Greatly enjoyed!!! Will stay again!!!

Reviewed on Jul 11, 2026

Cayman Suites Hotel

Cayman Suites Hotel

2 out of 5
North Ocean City
Price was $1,426, price is now $1,176 per person
$1,176
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
7.6/10 Good! (1,010 reviews)
Parking was good. Furniture and TVs are probably 20 years old. I think this place is very overpriced!

Reviewed on Jul 19, 2026

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

3 out of 5
Midtown Ocean City
Price was $1,519, price is now $1,258 per person
$1,258
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
7.4/10 Good! (1,309 reviews)
Worst hotel I’ve ever stayed in. They completely lie on the advertisement with pictures that aren’t real, charge you full price for a half functioning hotel because of “renovations” (they should be closed), you have to request room service that is an absolute joke (no bed changing, no leaving fresh towels… had to be requested multiple times & we still had to do it ourselves as if we didn’t pay money to stay there) & the hot tub was broken our entire stay. Upon complaining, no sympathy was given. Basically told it was “too bad” when the room was pricey. This place should be ashamed of themselves. I would give it 0 stars if possible.

Reviewed on Jul 18, 2026

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Assawoman Hotel Deals

Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Aug 16 to Aug 17
$134 total
Aug 16 - Aug 17
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Room's were clean and comfortable close to restaurants and ice cream shops and donuts short drive to the beach"

Reviewed on Jul 19, 2026

Chincoteague Inn
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St Chincoteague VA
$399 nightly
The price is $448 total per night from Jul 21 to Jul 22
$448 total
Jul 21 - Jul 22
Total with taxes and fees
9.6/10 Exceptional! (288 reviews)
"We loved our stay at Blu-Fin! The bungalows were comfortable and modern. The site was quiet and clean and communication with the host was clear. We’ll be back!"

Reviewed on Jul 15, 2026

Blufin Bungalows & Marina
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
$333 nightly
The price is $373 total per night from Aug 9 to Aug 10
$373 total
Aug 9 - Aug 10
Total with taxes and fees
Key West Cottages
See all 791 properties in Assawoman
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 Assawoman Vacation Packages

Assawoman Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does an Assawoman vacation package cost?
You can pick up a vacation package to this popular destination from $780 on Expedia. However, how much your vacation to Assawoman costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Assawoman?
If you're looking to score a cheap Assawoman vacation package, consider visiting in November, December and January. You'll typically find lower prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Assawoman?
The ideal length of your Assawoman vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to check out all the major attractions and explore some hidden treasures along the way.
How to find the best Assawoman package deals?
Landing a cheap Assawoman package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Assawoman package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Assawoman vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Assawoman vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Assawoman?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Assawoman break.
Does Expedia offer Book Now, Pay Later Assawoman vacation packages?
Your Assawoman getaway is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.