Assawoman Vacation Rentals

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Our top choices for Assawoman vacation rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (510 reviews)
"This was a Wonderful place to stay!! So much charm a the staff was wonderful! "
United States
CHRISTIE
Key West Cottages

Cozy cottage w/ creekside fire pit & pet-friendly

Cozy cottage w/ creekside fire pit & pet-friendly
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 CA $187
CA $398 total
includes taxes & fees
Feb 23 - Feb 24
Cozy cottage w/ creekside fire pit & pet-friendly

Flamingo Villa

Flamingo Villa
Piney Island
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 CA $136
CA $267 total
includes taxes & fees
Feb 23 - Feb 24
Flamingo Villa

Sunset Villa

Sunset Villa
Piney Island
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 CA $135
CA $266 total
includes taxes & fees
Feb 21 - Feb 22
Sunset 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, (66 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is CA $123
CA $349 total
includes taxes & fees
Feb 21 - Feb 22
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

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, (25 reviews)
"Loved that it was right on the bay. "
United States
Debra
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

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.
The price is CA $135
CA $266 total
includes taxes & fees
Feb 21 - Feb 22
Coral Villa

The purple door at the bay.

The purple door at the bay.
Captain's Cove
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 CA $215
CA $612 total
includes taxes & fees
Feb 22 - Feb 23
The purple door at the bay.

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, (42 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $143
CA $545 total
includes taxes & fees
Feb 22 - Feb 23
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Only 5 minutes to Assateague National Seashore!

Only 5 minutes to Assateague National Seashore!
Chincoteague
8.8 out of 10, Excellent, (10 reviews)
"Quiet area and close to all attractions. Very fast response with any questions before and during stay. Would recommend!"
United States
Sue S.
The price is CA $137
CA $259 total
includes taxes & fees
Feb 22 - Feb 23
Only 5 minutes to Assateague National Seashore!

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 CA $137
CA $259 total
includes taxes & fees
Feb 22 - Feb 23
A Bargain on Chincoteague Island!

Only 5 min from Assateague National Seashore!

Only 5 min from Assateague National Seashore!
Chincoteague Island
7.4 out of 10, Good, (3 reviews)
"Low-quality furniture. needs to be updated"
United States
Susan E.
The price is CA $137
CA $259 total
includes taxes & fees
Feb 22 - Feb 23
Only 5 min from Assateague National Seashore!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.4 out of 10, Exceptional, (8 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is CA $163
CA $292 total
includes taxes & fees
Feb 22 - Feb 23
Only 5 min. from the Beach!

Only 5 min to Assateague National Seashore!

Only 5 min to Assateague National Seashore!
Chincoteague Island
8.0 out of 10, Very good, (6 reviews)
"The property and room were clean and neat. The facility and rooms are older, but all was functional and clean. Very communicative and easy and clear check in and out process! "
United States
Ellen K.
The price is CA $137
CA $259 total
includes taxes & fees
Feb 22 - Feb 23
Only 5 min to Assateague National Seashore!

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, (7 reviews)
"Beautiful home with everything needed for comfort and a great time! Great location for getting to the beach, shopping and dining out. Communication with host was very informative and helpful. Thank you Chip!"
United States
Gil R.
The price is CA $164
CA $383 total
includes taxes & fees
Mar 3 - Mar 4
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
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 CA $138
CA $260 total
includes taxes & fees
Mar 5 - Mar 6
Only 5 min. from the Beach!

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, (7 reviews)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
United States
William M.
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (19 reviews)
"Was wonderfully comfortable and clean. Would definitely recommend. "
United States
Joy D.
The price is CA $183
CA $364 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Barn Loft: Country Views & Central to Beaches

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 CA $136
CA $550 total
includes taxes & fees
Feb 24 - Feb 25
The Neigh-Neigh - Location! Location! Location!

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 CA $207
CA $432 total
includes taxes & fees
Feb 22 - Feb 23
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
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

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.