Assawoman Vacations from $709

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The Latest Assawoman vacation packages

Price found within the past 48 hours. Click for updated prices.
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $786, price is now $709 per person
$709
per person
Nov 18 - Nov 21
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9/10 Wonderful! (756 reviews)
The property is in a very convenient location in downtown Bethany and right on the beach; however, I was a little disappointed with the hotel itself. The pool was claimed to be heated but it was not. The cleaning service was poor and honestly, the "amenities" that were offered at the hotel, were not what was advertised on the site when booking. Overall, nice place to stay for convenience, but not the ideal place as far as cleanliness and hotel amenities go

Reviewed on Sep 1, 2025

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
Price was $899, price is now $806 per person
$806
per person
Nov 18 - Nov 21
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9.4/10 Exceptional! (626 reviews)
Great location and rooms. Great place!

Reviewed on Sep 25, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,586, price is now $1,470 per person
$1,470
per person
Nov 28 - Nov 30
just found
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

The Burgundy Inn

The Burgundy Inn

2.5 out of 5
Downtown Ocean City
Price was $1,180, price is now $1,107 per person
$1,107
per person
Nov 28 - Nov 30
just found
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
6.8/10 (593 reviews)
Exactly what we needed for a mini vacay! Everyone at the front desk was helpful and personable!

Reviewed on Sep 2, 2025

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3 out of 5
Price was $822, price is now $785 per person
$785
per person
Nov 18 - Nov 21
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9.2/10 Wonderful! (22 reviews)
Great spot and well appointed. Great communicator. HVAC loud and might consider brighter bulbs in lamps.

Reviewed on Nov 17, 2024

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Assawoman Hotel Deals

Waterside Inn

Waterside Inn

2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Oct 27 to Oct 28
$77 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (1,022 reviews)
"Lovely property, convenient walking to town and water"

Reviewed on Sep 25, 2025

Waterside Inn
Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

2.5 out of 5
3801 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Oct 26 to Oct 27
$90 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (987 reviews)
"Clean room and staff was great"

Reviewed on Sep 12, 2025

Marina Bay Hotel & Suites, an Ascend Collection Hotel
Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

2.5 out of 5
4195 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Oct 26 to Oct 27
$129 total
Oct 26 - Oct 27
Total with taxes and fees
9.6/10 Exceptional! (1,010 reviews)
A Nice Hotel
"A beautiful waterfront hotel. The staff wee friendly and welcoming. The room was spacious and clean. I would highly recommend this hotel."

Reviewed on Sep 23, 2025

Comfort Suites Chincoteague Island Bayfront Resort
See all 793 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 $709 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.