Assawoman Holidays

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Top hotels in Assawoman

Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
The price is €117 per night from 12 Jul to 13 Jul
€117
12 Jul - 13 Jul
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Easy check in and very respectable"

Reviewed on 4 Jul 2026

Chincoteague Inn
Chincoteague Bay RV Resort & Cottages

Chincoteague Bay RV Resort & Cottages

3 out of 5
2305 Main St Chincoteague VA
9.8/10 Exceptional! (8 reviews)
"The views and amenities were spectacular - views of sunrise and sunset and a gorgeous boardwalk all around!"

Reviewed on 28 Jun 2026

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Chincoteague Bay RV Resort & Cottages
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
The price is €301 per night from 4 Aug to 5 Aug
€301
4 Aug - 5 Aug
includes taxes & fees
9.8/10 Exceptional! (592 reviews)
"Will be coming here every single time me and my bf are in Assateague moving forward. I have no complaints other than how I wish I could stay another night. Everyone was so friendly and communicated well when I had my own problems, getting things figured out before we even arrived. I really appreciate ..."

Reviewed on 4 Jul 2026

Key West Cottages
See all 789 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 holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages and you could land some great off-season deals.
How many days is enough for Assawoman?
The ideal length of your Assawoman holiday 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," "Traveller 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Assawoman holiday as a package?
Expedia holiday 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 holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 personalised Assawoman holiday package.

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.