Holiday Rentals in Assawoman

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Our top choices for Assawoman holiday rentals

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, (65 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 €323
includes taxes & fees
28 May - 29 May
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (562 reviews)
"Great place to stay on the island"
United States
Wilmer
The price is €211
includes taxes & fees
26 May - 27 May
Key West Cottages

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
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 €302
includes taxes & fees
21 May - 22 May
Pet-friendly creekside cottage w/ backyard

Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue 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 €176
includes taxes & fees
27 May - 28 May
Assateageue Inn 104 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 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 €180
includes taxes & fees
31 May - 1 Jun
Assateague Inn 213 by Seaside Vacations & Sales

Flamingo Villa

Flamingo Villa
Piney Island
10.0 out of 10, Exceptional, (3 reviews)
"It was perfect for a quick little get away the property had everything that was needed and very clean. "
United States
Olivia P.
Flamingo Villa

Sand Dollar Villa

Sand Dollar Villa
Piney Island
10.0 out of 10, Exceptional, (5 reviews)
"Clean close to everything good communication with owners very enjoyable "
United States
tracy s.
Sand Dollar Villa

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, (71 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is €287
includes taxes & fees
21 May - 22 May
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (56 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is €382
includes taxes & fees
25 May - 26 May
The purple door at the bay.

Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!
3.0 star property
Captain's Cove
The price is €432
includes taxes & fees
21 May - 22 May
Greenbackville Retreat w/ Deck: 1 Mi to Marina!

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 Neigh-Neigh - Location! Location! Location!

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 €373
includes taxes & fees
25 May - 26 May
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Sunset Villa

Sunset Villa
Piney Island
10.0 out of 10, Exceptional, (6 reviews)
"Fun family time!"
United States
Nancy C.
The price is €267
includes taxes & fees
28 May - 29 May
Sunset Villa

Assateague Inn 102 by Seaside Vacations & Sales

Assateague Inn 102 by Seaside Vacations & Sales
Downtown Chincoteague
8.6 out of 10, Excellent, (8 reviews)
"Perfect location, unit was exactly as listed, very clean, had the essentials. We very much enjoyed our stay and the ease of checking in and out was the cherry on top."
United States
Julia S.
Assateague Inn 102 by Seaside Vacations & Sales

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore
Onancock
9.8 out of 10, Exceptional, (9 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 €192
includes taxes & fees
27 May - 28 May
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

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 €266
includes taxes & fees
26 May - 27 May
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (253 reviews)
"My kids and I had a wonderful spring break stay at the bungalows!"
United States
Susan
The price is €256
includes taxes & fees
29 May - 30 May
Blufin Bungalows & Marina

Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!
Captain's Cove
The price is €434
includes taxes & fees
21 May - 22 May
Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Deep Hole
10.0 out of 10, Exceptional, (9 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 €255
includes taxes & fees
27 May - 28 May
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
The price is €278
includes taxes & fees
21 May - 22 May
Cozy 2-bedroom house in Chincoteague
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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Top Assawoman Hotel Reviews

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, apart-hotels, 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 favorite 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 depends 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 €176 per night. Entering your travel dates in the search wizard you might find 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.