Assawoman Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Assawoman Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Downtown Ocean City
CA $978
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
7.8/10 Good! (114 reviews)
Room wasn’t very clean when I arrived, I found dead beetles and toilet paper pieces on the floor. The bedding was stained.
Reviewed on Sep 2, 2026
Beach Bum Inn
Downtown Ocean City
CA $958
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
8.2/10 Very good! (334 reviews)
The only complaints I have was finding two pieces of clothing under the bed and the toilet seat kept falling off. The mattress from the pull out couch had stains on it.
Reviewed on Aug 30, 2026
Comfort Suites Ocean City West
West Ocean City
CA $1,014
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
8.4/10 Very good! (1,001 reviews)
Room was clean but we had TV issues, the bathroom had a bit of mold in the corner, and the pool area looked like it could use some new decorations. But other than that, solid place to stay for 2 nights!
Reviewed on Sep 3, 2026
Sea Bay Hotel
Midtown Ocean City
CA $963
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Salisbury (SBY)
8.2/10 Very good! (663 reviews)
Staff were friendly and helpful and the location was great. Parking was convenient.
Only complaint was musty odor to room. Otherwise nice stay.
Reviewed on Sep 3, 2026
Ready to book your vacation to Assawoman?
Assawoman Hotel Deals
Waterside Inn
3761 Main St Chincoteague VA
CA $119
CA $134 total
Sep 29 - Sep 30
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Convenient location, clean, loved fishing and crabbing right off their pier. Bonus was watching the perfect sunset right off our balcony."
Reviewed on Sep 3, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
CA $123
CA $138 total
Sep 27 - Sep 28
includes taxes & fees
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
Fully refundable
CA $184
CA $208 total
Oct 4 - Oct 5
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"I wish they had a sign to keep the noise down at night. I came to rest but the people above me made so much noise after 10pm and I think they need some kind of signage to keep quiet after a certain time….that would be the suggestion that I have."
Reviewed on Sep 1, 2026
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.
Frequently asked questions
How much does an Assawoman vacation package cost?
You can pick up a vacation package to this destination from CA $944 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?
- Pick your dates: What you want to do in Assawoman and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
