Assawoman vacation rentals

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August 2025

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Scroll through and select from vacation rentals in Assawoman to find one that's perfect for your trip. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as parking and air conditioning. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Assawoman

Showing deals for:Nov 7 - Nov 14

Exceptional

(32 reviews)

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Temperanceville, VA

10% off

All fees included

Exceptional

(13 reviews)

Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes,Julycancellation

Chincoteague, VA

12% off

All fees included

Exceptional

(6 reviews)

Riptide’s Crossing: A waterfront getaway w/deep water dock and incredible views

Chincoteague, VA

8% off

All fees included

Exceptional

(49 reviews)

QUIET, pet-friendly nature retreat with HOT TUB & without getting BIT!

Temperanceville, VA

13% off

All fees included

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Assawoman

Atlantic Vacation Rental | 3BR | 2BA | Step-Free Entry Via Ramp | 1,568 Sq Ft

11 Mi to Chincoteague: Atlantic Home w/ Decks!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Chincoteague Hideaway - Close to town - Linens and Towels Provided - No pets

Sleeps 8 · 3 bedrooms · 2 bathrooms

Trails End Campground 20 min-Chincoteague Island 40 min-OCMD 2 hrs-VA Beach

Sleeps 6 · 1 bedroom · 1 bathroom

Top rated rentals - Assawoman

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Find out more about Assawoman

Book a vacation rental for your Assawoman getaway

Experience the unique character of Assawoman with a stay in a vacation home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Assawoman

Do you want to discover attractions to visit in the area? Venture out of your vacation home and check out everything that makes Assawoman a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

Maui Jack's Waterpark (9.8 mi / 15.8 km)
Captain's Cove Golf and Yacht Club (10 mi / 16.1 km)
North Street Market (16.6 mi / 26.7 km)
SouthEast Expeditions (16.7 mi / 26.9 km)
Bloxom Winery (6.6 mi / 10.6 km)

Exploring the natural features in Assawoman

Whether you're an outdoor enthusiast or just want to take in the scenery, Assawoman is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

Chincoteague Channel (6.4 mi / 10.3 km)
Assateague Point (7.9 mi / 12.6 km)
Robert N. Reed Downtown Waterfront Park (9 mi / 14.5 km)
Chincoteague National Wildlife Refuge (10.8 mi / 17.4 km)
Oyster Bay (11.4 mi / 18.4 km)
Thurf Marsh Islands (12.9 mi / 20.7 km)

Frequently asked questions

What is the best area to stay in Assawoman when booking a vacation rental?

When considering a vacation rental in Assawoman, Virginia, one of the most appealing areas to stay is the coastal community near Chincoteague Island. This charming locale offers a delightful blend of natural beauty and local culture. With a variety of vacation properties available, ranging from cozy cottages to spacious beach homes, visitors can easily find accommodations that suit their needs.

Staying near Chincoteague Island places you in proximity to the famous Assateague Island National Seashore, where you can explore pristine beaches, scenic trails, and the iconic wild ponies that roam freely. This area is superb for nature enthusiasts, offering opportunities for birdwatching, kayaking, and hiking. Additionally, the nearby Chincoteague National Wildlife Refuge is a fantastic spot for those interested in observing local wildlife and enjoying tranquil landscapes.

Another charming neighborhood to consider is the area surrounding the historic town of Pocomoke City. This area boasts a rich history and provides easy access to the Pocomoke River, where visitors can enjoy fishing, boating, and picnicking along the scenic banks.

How much does it cost to rent a vacation home in Assawoman?

Prices for vacation rentals in Assawoman vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Assawoman to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Assawoman vacation house rentals?

You can find great discounts on house rentals in Assawoman on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay vacation rentals in Assawoman?

A long-stay vacation rental in Assawoman is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Are there any Assawoman vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Assawoman with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

How early should I book a Assawoman vacation rental?

Book your Assawoman vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Assawoman?

In Assawoman, Virginia, visitors can explore the natural beauty of the Eastern Shore. The Chincoteague National Wildlife Refuge, located nearby, offers opportunities for wildlife viewing and scenic walks along the beach. Vacation rentals in the area often provide easy access to the stunning Assateague Island, known for its wild ponies and pristine beaches, ideal for those seeking outdoor adventures.

For a taste of local culture, the charming town of Onancock is just a short drive away, featuring historic architecture, quaint shops, and delightful dining options. The nearby Tangier Island, accessible by boat, is another point of interest, known for its unique culture and beautiful scenery.

Can I change or cancel my Assawoman home rental booking on Vrbo?

To find Assawoman vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Assawoman vacation rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.