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Assawoman Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Assawoman holiday rentals

A waterfront house with a balcony, dock, and a view of the water.

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (660 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is NZ$405
includes taxes & fees
18 Oct - 19 Oct
Key West Cottages
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

2. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is NZ$357
includes taxes & fees
18 Oct - 19 Oct
Assateageue Inn 104 by Seaside Vacations & Sales
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

3. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (71 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is NZ$791
includes taxes & fees
20 Oct - 21 Oct
Bayfront Modern Retreat • Dock, Kayaks, Views
A two-story building with a central entrance and a wooden walkway leading to it.

4. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"We had a mommy-daughter mini-getaway to celebrate her 9th birthday! The area is very walkable, but also easy to drive and navigate the rest of the island. Our room was clean, as advertised, and the perfect place to relax, eat, and recharge. We loved the pool! The check-in/check-out process was very easy."
United States
Nora T.
The price is NZ$379
includes taxes & fees
18 Oct - 19 Oct
Assateague Inn 203 by Seaside Vacations & Sales
A sandy beach with footprints and a person walking.

5. 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, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is NZ$708
includes taxes & fees
16 Oct - 17 Oct
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A covered porch with a red swing chair, white chairs, and a view of the street.

6. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay close to town. Charming screened porch, well appointed kitchen, plenty of space for us."
United States
Veronika B.
The price is NZ$650
includes taxes & fees
25 Oct - 26 Oct
The Neigh-Neigh - Location! Location! Location!
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

7. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
9.8 out of 10, Exceptional, (19 reviews)
"Great location, easy check in, very clean, well decorated"
United States
sue g.
The price is NZ$574
includes taxes & fees
16 Oct - 17 Oct
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

8. Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (10 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is NZ$518
includes taxes & fees
20 Oct - 21 Oct
Central Location~Walk 2 Dining! Beach Pass & Gear!
A sunroom with wicker furniture, large windows, and a view of the water.

9. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Great location"
United States
Rick K.
The price is NZ$795
includes taxes & fees
20 Oct - 21 Oct
The purple door at the bay.
A covered porch with wicker chairs and a view of the outdoors.

10. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
The price is NZ$628
includes taxes & fees
21 Oct - 22 Oct
Pet-friendly creekside cottage w/ backyard
A covered outdoor seating area with wooden benches and a glass door leading to a room with a sofa and a bed.

11. Assateague Inn 102 by Seaside Vacations & Sales

Assateague Inn 102 by Seaside Vacations & Sales
Downtown Chincoteague
8.6 out of 10, Excellent, (10 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 beach with waves and a sunset.

12. 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, (83 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is NZ$483
includes taxes & fees
15 Nov - 16 Nov
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
A staircase with a dark door at the bottom and a light fixture above it.

13. 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, (28 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is NZ$556
includes taxes & fees
16 Oct - 17 Oct
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
A living room with a blue sofa, a wooden dining table with chairs, a TV, and a balcony with blue curtains.

14. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (9 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
The price is NZ$357
includes taxes & fees
18 Oct - 19 Oct
Assateague Inn 106 by Seaside Vacations & Sales
A two-story house with a front porch, a number '23314' on the door, and a small bench.

15. 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, (22 reviews)
"Beautiful property, very accommodating hosts, ideal location for our visit. We look forward to future visits "
United States
Deborah G.
The price is NZ$623
includes taxes & fees
16 Oct - 17 Oct
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3
A cozy living room with a sofa, a coffee table, and a TV mounted on the wall.

16. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (6 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 NZ$371
includes taxes & fees
16 Oct - 17 Oct
Cozy 2-bedroom house in Chincoteague
A hallway with striped sofas, a wooden floor, and wall-mounted lights.

17. The Glick - Short Stays on Market

The Glick - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (6 reviews)
"Our weekend stay at The Glick was perfect!! The apartment was very clean, comfortable and nicely decorated, just like the pictures show. We really appreciated the Keurig coffee machine and comfy bed. All instructions for check in and check out were very clear and simple. We were within walking distance to several restaurants and shops. The town of Onancock is so peaceful and charming. The sunsets at the Wharf are beautiful. This is a wonderful location to stay while visiting on the Eastern Shore"
United States
Tara M.
The price is NZ$424
includes taxes & fees
18 Oct - 19 Oct
The Glick - Short Stays on Market
A two-story building with a central entrance and a wooden walkway leading to it.

18. Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Lauren P.
The price is NZ$357
includes taxes & fees
29 Oct - 30 Oct
Assateague Inn 213 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

19. Assateague Inn 103 by Seaside Vacations & Sales

Assateague Inn 103 by Seaside Vacations & Sales
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 NZ$357
includes taxes & fees
20 Oct - 21 Oct
Assateague Inn 103 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

20. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (37 reviews)
"The location was central with a deck out on the marsh, which was lovely. The pool seemed well kept and was nice. It was clean and the communication with the hosts was quite good. The smart TVs didn’t really work and could only work with live tv. No apps worked. Overall, though, would stay again."
United States
Erin
The price is NZ$360
includes taxes & fees
29 Oct - 30 Oct
Assateague Inn 111 by Seaside Vacations & Sales
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

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

10/10 Excellent
"Great place to stay, super clean, accommodating and comfortable. My boys loved fishing on the pier!"
lauren 1-night trip
Posted 6 hours ago
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

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 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 NZ$357 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.