Assawoman Vacation Packages

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Top Assawoman Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
per person
Aug 22 - Aug 25
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.8/10 Good! (1,001 reviews)
a little outdated but convenient and walkable which was the most important part. most of the time was spent at the beach. tied to a bar named finnigans but the best part was being right next door to seacrets and the beach goo stay

Reviewed on Jul. 1, 2025

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
per person
Aug 22 - Aug 25
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.2/10 Good! (150 reviews)
Granddaughter love the pool

Reviewed on Jul. 2, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Aug 22 - Aug 25
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (2,932 reviews)
Plenty of parking, Cleaning Ness, Staff was great and helpful with frequently ask questions. Will return. Thanks

Reviewed on Jul. 2, 2025

Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
per person
Aug 22 - Aug 25
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very Good! (762 reviews)
Right on the boardwalk. Convenient stores nearby. I have a Tacoma and parking was kind of tight, recommend a small car if parking.

Reviewed on Jun. 30, 2025

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
Aug 22 - Aug 25
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.2/10 Very Good! (1,267 reviews)
We love the all in one atmosphere with the couple of bars and the wonderful sunroom. The beach side bar was definitely a favorite. We love the fact that umbrellas and beach chairs were included and even had bar service on the beach. However, there were a couple things that made it less than perfect stay. The ice machines for the most part didn’t work except on floor three, and we were on floor 15. We had asked for non-allergenic bedding and had to ask for it a second time. All of the staff were kind and helpful, and the price was right for the included amenities. Would definitely return.

Reviewed on Jul. 2, 2025

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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
The price is CA $175 per night from Jul 6 to Jul 7
CA $175
CA $197 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Rooms were clean and spacious. Just minutes from Assateague Island. Lots of dining options close by."

Reviewed on Jul. 2, 2025

Chincoteague Inn
Refuge Inn
Refuge Inn
3 out of 5
7058 Maddox Blvd., Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Jul 13 to Jul 14
CA $245
CA $276 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
"The ponies are on view close to the motel. We haven't visited for a number of years and recognize that the rooms have been refurnished. Having a desk is always a plus if traveling with a computer and then to have a cafe size table made the king room seem like a suite. The pool is very pleasant and ..."

Reviewed on Jul. 1, 2025

Refuge Inn
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
The price is CA $133 per night from Jul 6 to Jul 7
CA $133
CA $150 total
Jul 6 - Jul 7
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"Property was nice, wish there was more parking though."

Reviewed on Jun. 24, 2025

Atlantic Shores Inn and Suites
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Assawoman vacation package cost?
You can pick up a vacation package to this destination from CA $1,258 on Expedia. However, how much your vacation to Assawoman costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Assawoman?
If you'd like to score a cheap Assawoman vacation package, consider visiting in January, February and November. You'll generally find lower rates on hotels and airfares during these months --- perfect for budget-conscious travellers.
How many days is enough for Assawoman?
You can visit all the main sights in Assawoman in a few days, including the must-see Kegotank Bay. If you're looking for an extended Assawoman vacation, look at what kind of activities and day tours are available nearby.
How to find the best Assawoman package deals?
Bagging a cheap Assawoman package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Assawoman package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Assawoman vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights individually. Better still, you can personalize your Assawoman trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Assawoman?
If you have your Assawoman travel dates confirmed, book early to bag some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Assawoman?

  1. Pick your dates: What you want to do in Assawoman and your preferred season will help you decide when to go.
  2. Budget wisely: On top of the price of your accommodations, you should factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Assawoman.
  3. Decide how long to go away for: Now that you're more familiar with Assawoman, you can figure out the ideal length of your vacation. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose an Assawoman vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.