Assawoman Vacations

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  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

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Find the Best Assawoman Vacation Packages

Assawoman Hotel Deals

Waterside Inn

Waterside Inn

2 out of 5
3761 Main St Chincoteague VA
The price is ￥8,786 per night from Nov 8 to Nov 9
￥8,786
￥9,865 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Excellent location, excellent staff and breakfast. The only down things - some rooms need furniture upgrades, such as chairs on the balcony, sliding door in our room was barely moving, window screen had gaps, shower curtain needed replacement. Otherwise, it is very good."

Reviewed on Oct 28, 2026

Waterside Inn
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
The price is ￥13,253 per night from Oct 31 to Nov 1
￥13,253
￥14,883 total
Oct 31 - Nov 1
includes taxes & fees
Chincoteague Inn
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
The price is ￥31,820 per night from Nov 9 to Nov 10
￥31,820
￥35,734 total
Nov 9 - Nov 10
includes taxes & fees
Key West Cottages
See all 792 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.

Frequently asked questions

How much does an Assawoman vacation package cost?
You can pick up a vacation package to this popular destination 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?
You can usually find lower prices and better availability in January, February and November. Browse our cheap Assawoman vacation packages and you could land some great off-season deals.
How many days is enough for Assawoman?
The ideal length of your Assawoman vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to go to all the main sights and explore some hidden gems 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.
How to plan a trip to Assawoman?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Assawoman.
  2. Set a budget: Factor in costs such as transportation, flights and meals when working out how much to put aside for your trip to Assawoman. Then, select a property that works with your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to get to in Assawoman. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Assawoman vacation package.

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