Default HTG hotel image

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

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Accomac
10.0 out of 10, Exceptional, (27 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is CA $213
CA $444 total
includes taxes & fees
Jul 20 - Jul 21
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3
Accomac
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful property, very accommodating hosts, ideal location for our visit. We look forward to future visits "
United States
Deborah G.
The price is CA $213
CA $497 total
includes taxes & fees
Jul 20 - Jul 21
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is CA $188
CA $372 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Barn Loft: Country Views & Central to Beaches

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (288 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
The price is CA $434
CA $566 total
includes taxes & fees
Jul 26 - Jul 27
Blufin Bungalows & Marina

Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (58 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is CA $114
CA $263 total
includes taxes & fees
Jul 26 - Jul 27
Cottage near the Bay

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (62 reviews)
"This is a great property with a great view of the bay. It's tucked away in a quiet little neighborhood in a nice and friendly community. Chincoteague is close by and it's not too far from Assateague. The property management team is excellent. They were extremely responsive to our questions and requests. They were patient with all our questions. Kelly was fantastic. The best hosts I've had."
United States
A Shabeen J.
The price is CA $245
CA $664 total
includes taxes & fees
Aug 8 - Aug 9
The purple door at the bay.

The Harbour - Short Stays on Market

The Harbour - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (2 reviews)
"The Harbour on Market in Onancock, VA was a gorgeous condo and we will absolutely love to vacation here again in the future. Everything was top notch and the amenities surpassed our expectations. We had an unfortunate incident beyond anyone’s control and needed to vacate sooner than expected; however, the owners were so amazing and accommodated our needs. We highly recommend this place! 5 FULL STARS!"
United States
Jennifer M.
The price is CA $202
CA $447 total
includes taxes & fees
Jul 27 - Jul 28
The Harbour - Short Stays on Market

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (599 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is CA $430
CA $483 total
includes taxes & fees
Aug 4 - Aug 5
Key West Cottages

Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (66 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is CA $299
CA $851 total
includes taxes & fees
Jul 22 - Jul 23
Bayfront Modern Retreat • Dock, Kayaks, Views

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (46 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $335
CA $795 total
includes taxes & fees
Aug 13 - Aug 14
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Everything was as it was stated. Clean, neat and stocked with essentials. Cozy and comfortable. Quiet and peaceful. Loved the island and will be coming back. "
United States
Kera S.
Assateague Inn 213 by Seaside Vacations & Sales

Palm Villa

Palm Villa
Piney Island
9.2 out of 10, Wonderful, (5 reviews)
"The property was exactly as advertised and met our expectations. The manager was very nice. We would have preferred check-in instructions ahead of time without needing to call, but did not have any problems with check-in or our stay. We enjoyed the location and close proximity to shops, restaurants, and the Chincoteague Wildlife Refuge. We would stay here again."
United States
Scott D.
The price is CA $251
CA $420 total
includes taxes & fees
Aug 2 - Aug 3
Palm Villa

Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (4 reviews)
"Very nice and well designed property. As soon as you open the door, you can tell that a lot of love and dedication came into designing this beautiful little cottage.Done with taste. Well located, away from the busy beach town center, yet very close to the main street (Maddox Street) and to the National Park where the beach is located.It will be our to-go-to place in the Island."
United States
Jean-Charles G.
The price is CA $283
CA $499 total
includes taxes & fees
Aug 17 - Aug 18
Cozy 2-bedroom house in Chincoteague

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (138 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is CA $404
CA $698 total
includes taxes & fees
Jul 23 - Jul 24
Pet-friendly creekside cottage w/ backyard

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.6 out of 10, Exceptional, (34 reviews)
"Great place to rent"
United States
Hazel T.
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
3.0 star property
Captain's Cove
The price is CA $554
CA $1,084 total
includes taxes & fees
Jul 26 - Jul 27
Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Captain's Cove
The price is CA $461
CA $1,110 total
includes taxes & fees
Jul 26 - Jul 27
Deck & EV Charger: Coastal Retreat 1 Mi to Marina

The Social - Short Stays on Market

The Social - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (2 reviews)
"Loved every thing about the rental, the furniture was trendy and comfy. The unit was also spacious and clean. We enjoyed walking to the harbor and window shopping thru town. Also, had an awesome lunch across the street and even went back for dinner."
United States
Karen S.
The price is CA $188
CA $402 total
includes taxes & fees
Jul 21 - Jul 22
The Social - Short Stays on Market

The Glick - Short Stays on Market

The Glick - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (2 reviews)
"My grandson and I stayed in The Glick for six nights so that he could attend kayak camp just a few blocks away at the harbor (which we also highly recommend). The apartment looked nice online, but it was even better than it appeared.First, it was very spacious. It has a full kitchen, which not all rental apartments have. There was plenty of counter space and having a full sized fridge, stove, and washer/dryer was nice for a long stay. The place looked pretty new and it was spotless. I also liked...
United States
Cary M.
The price is CA $199
CA $433 total
includes taxes & fees
Jul 21 - Jul 22
The Glick - Short Stays on Market

The Lilliston - Short Stays on Market

The Lilliston - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (1 review)
"Comfortable , nice interior design, great location , lovely unit"
United States
Sena B.
The price is CA $187
CA $429 total
includes taxes & fees
Jul 27 - Jul 28
The Lilliston - Short Stays on Market
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Assawoman. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.