Assawoman Vacations from $300

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The Latest Assawoman vacation packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
per person
Nov 6 - Nov 10
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.2/10 Good! (156 reviews)
Hotel service was good, room had beds flipped but worked out well, also had a balcony

Reviewed on Aug 10, 2025

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.4/10 Very Good! (26 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice). The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.

Reviewed on Aug 9, 2025

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 21
found 14 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9/10 Wonderful! (748 reviews)
Great location for activities on the beach

Reviewed on Jul 31, 2025

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
Nov 6 - Nov 10
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.2/10 Very Good! (1,446 reviews)
Food at hotel was expensive and ok- better options available for a better quality food. Dislike the balcony being so small you can’t sit outside and enjoy it

Reviewed on Aug 11, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (32 reviews)
Nothing good about this place beside the bay view from balcony. Couches in the living room were torn, master bed was creaking, bathroom outdated, peeling paint, bathtub didn't drain water, peeling paint in the kitchen, fridge,, really old property, unappealing entrance

Reviewed on Jul 20, 2025

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Assawoman Hotel Deals

Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites

2 out of 5
6273 Maddox Blvd, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from Sep 8 to Sep 9
$95 total
Sep 8 - Sep 9
Total includes taxes and fees
7.2/10 Good! (1,010 reviews)
"Comfy beds, clean as a whistle, great location. Will defintely stay here again"

Reviewed on Aug 8, 2025

Atlantic Shores Inn and Suites
Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $109 total per night from Sep 7 to Sep 8
$109 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (1,008 reviews)
"Had a wonderful time during our stay here in July. Rooms are very nice and have your basic needs. Husband Loved the fact we could put the boat in their Marina Where he was able to keep an eye out..and of course, the convenience of it all. The Beds were soft and comfy..The Breakfast Bar every morning ..."

Reviewed on Aug 10, 2025

Waterside Inn
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Sep 1 to Sep 2
$111 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,006 reviews)
"Room was updated and comfortable. Staff was the best. Line up early for Captain Zack across the street! 2 hr wait for dinner"

Reviewed on Aug 9, 2025

Chincoteague Inn
See all 787 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.

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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 $300 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.