Assawoman Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Ready to book your vacation to Assawoman?

 

Choose your dates

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 $167 per night from Aug 16 to Aug 17
CA $167
CA $187 total
Aug 16 - Aug 17
includes taxes & fees
Chincoteague Inn
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St Chincoteague VA
The price is CA $434 per night from Jul 26 to Jul 27
CA $434
CA $566 total
Jul 26 - Jul 27
includes taxes & 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
The price is CA $430 per night from Aug 4 to Aug 5
CA $430
CA $483 total
Aug 4 - Aug 5
includes taxes & fees
9.8/10 Exceptional! (599 reviews)
"The aesthetic of the cottages is quintessential beach chic, which I appreciate. We stayed in one of the Key Lime cottages which had plenty of space for two people. Sunsets here are hard to beat and if you're a birder, there is a crazy amount of waterfowl that come right up to the docks. The bathroom ..."

Reviewed on Jul 17, 2026

Key West Cottages
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.
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 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.

Explore a world of travel with Expedia

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