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Assawoman Holiday Rentals

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Our top choices for Assawoman holiday rentals

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (623 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is NZ$414
includes taxes & fees
7 Sept - 8 Sept
Key West Cottages

2. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. I’ve stayed at Assateague Inn on several occasions over the years but this was my first time in 203 and by far the nicest one I’ve stayed in. Newly renovated and tastefully d"
United States
Annette H.
The price is NZ$342
includes taxes & fees
13 Sept - 14 Sept
Assateague Inn 203 by Seaside Vacations & Sales

3. 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$725
includes taxes & fees
30 Aug - 31 Aug
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

4. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
The price is NZ$754
includes taxes & fees
4 Sept - 5 Sept
The purple door at the bay.

5. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"Overall nice stay!"
United States
Becky S.
The price is NZ$804
includes taxes & fees
1 Sept - 2 Sept
Bayfront Modern Retreat • Dock, Kayaks, Views

6. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (32 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$333
includes taxes & fees
14 Sept - 15 Sept
Assateageue Inn 104 by Seaside Vacations & Sales

7. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful space. Lots of space for sleeping options. Easy check in process. Close to different shops!"
United States
Virginia D.
The price is NZ$558
includes taxes & fees
8 Sept - 9 Sept
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

8. 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$520
includes taxes & fees
31 Aug - 1 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

9. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is NZ$615
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Downtown: Tranquil Abode in Chincoteague!

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$738
includes taxes & fees
28 Sept - 29 Sept
Pet-friendly creekside cottage w/ backyard

11. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 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 NZ$449
includes taxes & fees
30 Aug - 31 Aug
Cozy Barn Loft: Country Views & Central to Beaches

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, (79 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is NZ$579
includes taxes & fees
27 Sept - 28 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

13. As close as you can get to the ocean south of Chincoteague

As close as you can get to the ocean south of Chincoteague
Parksley
10.0 out of 10, Exceptional, (139 reviews)
"Awesome place for a couple or small group that likes to be away from crowds. Quiet. Dark. Our 4th time. Hopefully more"
United States
brooks h.
The price is NZ$867
includes taxes & fees
19 Sept - 20 Sept
As close as you can get to the ocean south of Chincoteague

14. 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.
The price is NZ$416
includes taxes & fees
13 Sept - 14 Sept
Assateague Inn 102 by Seaside Vacations & Sales

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$582
includes taxes & fees
31 Aug - 1 Sept
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

16. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$532
includes taxes & fees
8 Sept - 9 Sept
Cozy 2-bedroom house in Chincoteague

17. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
9.8 out of 10, Exceptional, (9 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
2 Mi to Downtown: Tranquil Abode in Chincoteague!

18. 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$560
includes taxes & fees
7 Sept - 8 Sept
Central Location~Walk 2 Dining! Beach Pass & Gear!

19. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
9.8 out of 10, Exceptional, (6 reviews)
"Loved staying at this house…plenty of room for everyone."
United States
ashley b.
The price is NZ$982
includes taxes & fees
9 Sept - 10 Sept
The Neigh-Neigh - Location! Location! Location!

20. 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$327
includes taxes & fees
28 Sept - 29 Sept
Assateague Inn 213 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

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$333 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.