Assawoman Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Assawoman vacation rentals

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (511 reviews)
"This was a Wonderful place to stay!! So much charm a the staff was wonderful! "
United States
CHRISTIE
Key West Cottages
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is ¥21,236
¥45,514 total
includes taxes & fees
Mar 4 - Mar 5
Cozy cottage w/ creekside fire pit & pet‑friendly
9.6 out of 10, Exceptional, (22 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is ¥15,685
¥29,402 total
includes taxes & fees
Mar 1 - Mar 2
Assateague Inn 104 by Seaside Vacations & Sales
9.8 out of 10, Exceptional, (61 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
The price is ¥12,766
¥70,129 total
includes taxes & fees
Mar 1 - Mar 2
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Villa in Piney Island

Sunset Villa
10.0 out of 10, Exceptional, (6 reviews)
"This place was perfect for myself, two adult daughters, and 5 year old grandson. We enjoyed the quiet location that was still close to everything. The indoor pool was a great way to end our busy days. Communication and check in was winderful. Will stay again!"
United States
Julie B.
The price is ¥15,431
¥30,183 total
includes taxes & fees
Mar 1 - Mar 2
Sunset Villa
10.0 out of 10, Exceptional, (66 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is ¥16,853
¥43,634 total
includes taxes & fees
Mar 2 - Mar 3
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Villa in Piney Island

Flamingo Villa
10.0 out of 10, Exceptional, (2 reviews)
"We were on the shore for a wedding and it was fun being a tourist on Chincoteague for a weekend. Plenty of fun things for an 8 year old to do."
United States
Kathy W.
The price is ¥15,431
¥30,533 total
includes taxes & fees
Mar 9 - Mar 10
Flamingo Villa
8.0 out of 10, Very Good, (8 reviews)
"What a lovely little space! Everything was clean and just as described. We loved the dock out over the marsh grasses and used it every day - especially since the beach was closed we could still feel close to the water. The staff were super friendly and helpful. "
United States
Mary Kalbach E.
The price is ¥15,703
¥29,435 total
includes taxes & fees
Mar 2 - Mar 3
Bella's Beach Retreat by Seaside Vacations & Sales
9.6 out of 10, Exceptional, (42 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is ¥16,366
¥62,666 total
includes taxes & fees
Mar 1 - Mar 2
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
10.0 out of 10, Exceptional, (19 reviews)
"Was wonderfully comfortable and clean. Would definitely recommend. "
United States
Joy D.
The price is ¥20,926
¥41,790 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Barn Loft: Country Views & Central to Beaches

Vacation Home in Captain's Cove

The purple door at the bay.
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is ¥24,550
¥70,232 total
includes taxes & fees
Mar 4 - Mar 5
The purple door at the bay.
7.4 out of 10, Good, (3 reviews)
"Low-quality furniture. needs to be updated"
United States
Susan E.
The price is ¥15,703
¥29,435 total
includes taxes & fees
Mar 2 - Mar 3
Only 5 min from Assateague National Seashore!

Villa in Piney Island

Coral Villa
8.4 out of 10, Very Good, (5 reviews)
"Close to the beach. Peaceful stay. My family enjoyed."
United States
Natasha M.
The price is ¥15,449
¥30,218 total
includes taxes & fees
Mar 1 - Mar 2
Coral Villa

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (9 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is ¥18,687
¥32,746 total
includes taxes & fees
Mar 2 - Mar 3
Only 5 min. from the Beach!
9.8 out of 10, Exceptional, (7 reviews)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
United States
William M.
The price is ¥7,584
¥29,021 total
includes taxes & fees
Mar 10 - Mar 11
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (31 reviews)
"I liked the location of the Inn on the island. The room(s) were very clean, well furnished and bed was super comfortable. "
United States
Marie E.
The price is ¥15,685
¥29,402 total
includes taxes & fees
Mar 5 - Mar 6
Only 5 min. from the Beach!
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is ¥23,708
¥49,533 total
includes taxes & fees
Mar 4 - Mar 5
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
10.0 out of 10, Exceptional, (7 reviews)
"My husband and I stayed here with our two pups for one night, and we truly wish we could have stayed longer. The home is exceptionally clean, cozy, and well-appointed with everything you could need. The beds were very comfortable, and the location is perfect—close to everything in Chincoteague. We’d happily stay here again and highly recommend it!"
United States
Alice J.
The price is ¥16,039
¥40,419 total
includes taxes & fees
Mar 3 - Mar 4
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Condo in Chincoteague Island

A Bargain on Chincoteague Island!
8.8 out of 10, Excellent, (3 reviews)
"Overall the place was nice enough for the cost. "
United States
Stacey S.
The price is ¥15,703
¥29,435 total
includes taxes & fees
Mar 23 - Mar 24
A Bargain on Chincoteague Island!

Vacation Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is ¥12,625
¥29,079 total
includes taxes & fees
Mar 7 - Mar 8
Cottage near the Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Assawoman Hotel Reviews

Find out more about Assawoman

Search for holiday rentals in Assawoman on Expedia! You can easily find your home rentals, villas, holiday apartments in Assawoman using one of the methods below:

  • View our selection of featured holiday rentals in Assawoman
  • Use the map to find apartments and other holiday homes in the Assawoman neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Assawoman while they last

Look no further and take a look at our great range of rental properties in Assawoman!

Frequently asked questions

Can I find vacation rentals in Assawoman?

Yes, we give you a choice of vacation rentals near popular local attractions in Assawoman, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Assawoman?

Blufin Bungalows & Marina: This vacation home rental near Assawoman is on the beach and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

What can I see and do in Assawoman?

While exploring the area, visit family-friendly sights like Wallops Flight Facility, or get outside and enjoy nature at Chincoteague Channel. In the larger area, you’ll find Assateague Point and Robert N. Reed Downtown Waterfront Park.

What are vacation rentals like in Assawoman?

Vacation rentals are private accommodations you can stay in for a couple days or more in Assawoman. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.