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Eastern Shore of Virginia Holiday Rentals

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Our top choices for Eastern Shore of Virginia holiday rentals

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (613 reviews)
"Absolutely adorable, clean and staff super friendly"
United States
Misty
The price is NZ$418
includes taxes & fees
8 Sept - 9 Sept
Key West Cottages

2. 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, (21 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$589
includes taxes & fees
25 Aug - 26 Aug
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

3. 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, (27 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is NZ$527
includes taxes & fees
25 Aug - 26 Aug
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

4. 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, (13 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 NZ$480
includes taxes & fees
17 Aug - 18 Aug
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

5. The Oak - Short Stays on Market

The Oak - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (2 reviews)
"Terrific property. Well appointed, comfortable, and situated in the heart of Onancock. I will be back!"
United States
Betty A.
The price is NZ$491
includes taxes & fees
16 Aug - 17 Aug
The Oak - Short Stays on Market

6. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (306 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
The price is NZ$615
includes taxes & fees
20 Aug - 21 Aug
Blufin Bungalows & Marina

7. The Captains Quarters located in Cape Charles, VA offers breathtaking views.

The Captains Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles
9.8 out of 10, Exceptional, (66 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
The price is NZ$591
includes taxes & fees
17 Aug - 18 Aug
The Captains Quarters located in Cape Charles, VA offers breathtaking views.

8. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful place by the ocean with a sunset so amazing it humbles you. Will stay here again. The host was excellent in communicating and helping out when required."
United States
Arun S.
The price is NZ$782
includes taxes & fees
7 Sept - 8 Sept
Smith Beach cottage w/ private sunset

9. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (35 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$349
includes taxes & fees
2 Sept - 3 Sept
Assateague Inn 111 by Seaside Vacations & Sales

10. 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$575
includes taxes & fees
10 Sept - 11 Sept
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

11. Park Place - Comfy Condo Close to Beach

Park Place - Comfy Condo Close to Beach
Kiptopeke
9.8 out of 10, Exceptional, (51 reviews)
"Quiet qnd very convenient"
United States
Hocine B.
The price is NZ$1,058
includes taxes & fees
2 Sept - 3 Sept
Park Place - Comfy Condo Close to Beach

12. Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (10 reviews)
"conveniently located, very nice and cozy, loved it"
United States
Will C.
The price is NZ$662
includes taxes & fees
19 Aug - 20 Aug
Oyster Oasis, Modern Loft in Historic Downtown

13. Sol Mate: Sunset Cape Charles Shore Retreat

Sol Mate: Sunset Cape Charles Shore Retreat
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (7 reviews)
"The house was great for our weekend stay. The king size bed was very comfortable and the bathroom was nice. Even in November we spent a lot of time on the porch and were able to eat on the picnic table in the back yard. The hosts were great and we would surely come back again."
United States
Elizabeth K.
The price is NZ$1,298
includes taxes & fees
27 Aug - 28 Aug
Sol Mate: Sunset Cape Charles Shore Retreat

14. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (66 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$760
includes taxes & fees
23 Aug - 24 Aug
The purple door at the bay.

15. Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views

Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views
Wachapreague
10.0 out of 10, Exceptional, (3 reviews)
"Cozy , comfortable, clean and all the amenities one would need. Wonderful helpful hosts. Wachapreague General Store just across the street with coffee and breakfast sandwiches that were out of this world. If you find yourself in need of a place to decompress The Artist Apartment in Wachapreague is certainly your destination."
United States
Frank W.
The price is NZ$900
includes taxes & fees
27 Aug - 28 Aug
Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views

16. 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$784
includes taxes & fees
20 Aug - 21 Aug
2 Mi to Downtown: Tranquil Abode in Chincoteague!

17. 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$545
includes taxes & fees
24 Aug - 25 Aug
Cozy 2-bedroom house in Chincoteague

18. Crab Crib Loft in Historic Downtown Cape Charles

Crab Crib Loft in Historic Downtown Cape Charles
Historic Downtown Cape Charles
9.4 out of 10, Exceptional, (6 reviews)
"Excellent accommodations, cleanliness, communication, and location. Highly recommended!"
United States
Aaron L.
The price is NZ$687
includes taxes & fees
2 Sept - 3 Sept
Crab Crib Loft in Historic Downtown Cape Charles

19. Cape Haven - Condo 1.5 Blocks from Beach

Cape Haven - Condo 1.5 Blocks from Beach
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (51 reviews)
"The condo is spacious and beautiful. Loved the layout, balcony, and proximity to shops, food, and the beach. We plan to make this an annual getaway!"
United States
Donna H.
The price is NZ$1,156
includes taxes & fees
2 Sept - 3 Sept
Cape Haven - Condo 1.5 Blocks from Beach

20. Tiny House close to the Beaches of Cape Charles

Tiny House close to the Beaches of Cape Charles
Cape Charles
10.0 out of 10, Exceptional, (1 review)
"I enjoyed staying here, solid place!"
United States
Charles B.
The price is NZ$561
includes taxes & fees
1 Sept - 2 Sept
Tiny House close to the Beaches of Cape Charles
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 Eastern Shore of Virginia Hotel Reviews

Find out more about Eastern Shore of Virginia

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Eastern Shore of Virginia holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Eastern Shore of Virginia. 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 Eastern Shore of Virginia. Seeing all the best attractions is bound to make you fall in love with Eastern Shore of Virginia. Who knows, you may even be tempted to extend your 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 holiday 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 Eastern Shore of Virginia short-term rentals, that won’t be hard to do.