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 S$173 per night from 16 Aug to 17 Aug
S$173
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Awesome third year at this motel"

Reviewed on 17 Jul, 2026

Chincoteague Inn
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3 out of 5
2477 Main St Chincoteague VA
The price is S$519 per night from 21 Jul to 22 Jul
S$519
21 Jul - 22 Jul
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 15 Jul, 2026

Blufin Bungalows & Marina
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
The price is S$445 per night from 4 Aug to 5 Aug
S$445
4 Aug - 5 Aug
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 17 Jul, 2026

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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.