Assawoman Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Assawoman
Waterside Inn
3761 Main St Chincoteague VA
S$125
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Staff was friendly, room was spacious and clean but there was hair on the pillows luckily I take my own linen . Located in a beautiful place, nice view from the room, breakfast was ok. Staff was friendly and helpful."
Reviewed on 30 Aug, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
S$127
13 Sept - 14 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"X"
Reviewed on 2 Sept, 2026
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
Fully refundable
S$199
1 Oct - 2 Oct
includes taxes & fees
9.6/10 Exceptional! (1,007 reviews)
"I wish they had a sign to keep the noise down at night. I came to rest but the people above me made so much noise after 10pm and I think they need some kind of signage to keep quiet after a certain time….that would be the suggestion that I have."
Reviewed on 1 Sept, 2026
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?
- 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.
- 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.
- 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.
- 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.
* 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.
