Assawoman Holiday Rentals

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Our top choices for Assawoman holiday rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (538 reviews)
"Great place to stay very clean great location "
United States
Philip
The price is AU$285
includes taxes & fees
29 Apr - 30 Apr
Key West Cottages

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (225 reviews)
"Everything was great dishes were provided had a stove microwave and full refrigerator and freezer. Even had sponge and soap to wash dishes. Very beautiful view."
United States
Steven
The price is AU$235
includes taxes & fees
16 Apr - 17 Apr
Blufin Bungalows & Marina

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
Captain's Cove
The price is AU$403
includes taxes & fees
16 Apr - 17 Apr
1 Mi to Resort Marina! Greenbackville Retreat

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
9.8 out of 10, Exceptional, (28 reviews)
"Loved that it was right on the bay. "
United States
Debra
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (63 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 AU$599
includes taxes & fees
14 Apr - 15 Apr
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Cozy creekside cottage w/fire pit & patio

Cozy creekside cottage w/fire pit & patio
Up the Neck
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 AU$471
includes taxes & fees
15 Apr - 16 Apr
Cozy creekside cottage w/fire pit & patio

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (25 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is AU$271
includes taxes & fees
15 Apr - 16 Apr
Assateague Inn 104 by Seaside Vacations & Sales

Sunset Villa

Sunset Villa
Piney Island
10.0 out of 10, Exceptional, (6 reviews)
"Fun family time!"
United States
Nancy C.
The price is AU$335
includes taxes & fees
14 Apr - 15 Apr
Sunset Villa

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (55 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is AU$571
includes taxes & fees
15 Apr - 16 Apr
The purple door at the bay.

Coral Villa

Coral Villa
Piney Island
8.4 out of 10, Very good, (5 reviews)
"Close to the beach. Peaceful stay. My family enjoyed."
United States
Natasha M.
Coral Villa

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, (26 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is AU$445
includes taxes & fees
14 Apr - 15 Apr
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

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, (43 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is AU$562
includes taxes & fees
16 Apr - 17 Apr
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Bella's Beach Retreat by Seaside Vacations & Sales

Bella's Beach Retreat by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very good, (8 reviews)
"Off season rates are really reasonable- place is as described- good location- good views- would stay again."
United States
Cindy H.
The price is AU$275
includes taxes & fees
27 Apr - 28 Apr
Bella's Beach Retreat by Seaside Vacations & Sales

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (67 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is AU$422
includes taxes & fees
20 Apr - 21 Apr
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is AU$307
includes taxes & fees
16 Apr - 17 Apr
Only 5 min. from the Beach!

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is AU$267
includes taxes & fees
15 Apr - 16 Apr
Cottage near the Bay

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (32 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 AU$275
includes taxes & fees
21 Apr - 22 Apr
Only 5 min. from the Beach!

A Bargain on Chincoteague Island!

A Bargain on Chincoteague Island!
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 AU$271
includes taxes & fees
15 Apr - 16 Apr
A Bargain on Chincoteague Island!

The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (4 reviews)
"Loved staying at this house…plenty of room for everyone."
United States
ashley b.
The price is AU$602
includes taxes & fees
18 Apr - 19 Apr
The Neigh-Neigh - Location! Location! Location!

Only 5 min to Assateague National Seashore!

Only 5 min to Assateague National Seashore!
Downtown Chincoteague
8.6 out of 10, Excellent, (8 reviews)
"The condo was a perfect weekend getaway. Newly renovated and close to the beach. Great location in town. The property managers were all so helpful and had great communication from the very start. Would definitely stay here again!"
United States
Hunter E.
The price is AU$353
includes taxes & fees
15 Apr - 16 Apr
Only 5 min to Assateague National Seashore!
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.
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Find out more about Assawoman

Everything you need to know about Assawoman holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Assawoman holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Assawoman holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Assawoman holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Assawoman. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Assawoman holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Assawoman holiday rentals we have selected for you start as low as AU$235 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Assawoman rentals

At Expedia, we put the best Assawoman holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Assawoman rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Assawoman holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Assawoman. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Assawoman?

Yes, there are holiday rentals close to the most popular sights in Assawoman, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Assawoman has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of 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 wider area, you’ll find Assateague Point and Robert N. Reed Downtown Waterfront Park.

What are holiday rentals like in Assawoman?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Assawoman. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a small group gathering.