Assawoman Vacations from $296
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The Latest Assawoman vacation packages
Price found within the past 48 hours. Click for updated prices.
The Lodge at Great Oak Landing
$296
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Salisbury (SBY)
8/10 Very Good! (103 reviews)
Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun.
Reviewed on Aug 30, 2026
Assawoman Hotel Deals
Waterside Inn
3761 Main St Chincoteague VA
$97 nightly
$109 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Our room was clean and the bed was very comfortable. Our view of the bay was amazing on the balcony, with beautiful sunsets. The room was nice and spacious just a little musty smelling and we had ants and fruitflies to deal with. I know that's common on the island. We bought ant spray and a plug ..."
Reviewed on Sep 5, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$89 nightly
$100 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
Fully refundable
$132 nightly
$149 total
Oct 5 - Oct 6
Total with taxes and fees
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.
Find the Best Assawoman Vacation Packages
Assawoman Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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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 $296 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.