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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, (623 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is £180
includes taxes & fees
7 Sept - 8 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, (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 £264
includes taxes & fees
30 Aug - 31 Aug
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

3. 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)
"Nice location. Quaint place. Nice for a couple getting away."
United States
Stephen C.
The price is £190
includes taxes & fees
31 Aug - 1 Sept
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

4. 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 £231
includes taxes & fees
31 Aug - 1 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

5. The Social - Short Stays on Market

The Social - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, recommend it and would stay there again."
United States
Roscoe B.
The price is £202
includes taxes & fees
1 Sept - 2 Sept
The Social - Short Stays on Market

6. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (16 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
The price is £326
includes taxes & fees
2 Sept - 3 Sept
Smith Beach cottage w/ private sunset

7. 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 £152
includes taxes & fees
14 Sept - 15 Sept
Assateageue Inn 104 by Seaside Vacations & Sales

8. The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles
9.8 out of 10, Exceptional, (71 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
The price is £265
includes taxes & fees
30 Aug - 31 Aug
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

9. Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (62 reviews)
"We loved our stay. The house was clean and the location is perfect. The house has aged into some wonky shifted floors but that did not bother us. It had everything we needed."
United States
Demmie M.
The price is £414
includes taxes & fees
14 Sept - 15 Sept
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

10. 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 £445
includes taxes & fees
2 Sept - 3 Sept
Park Place - Comfy Condo Close to Beach

11. 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 £147
includes taxes & fees
1 Sept - 2 Sept
Assateague Inn 111 by Seaside Vacations & Sales

12. 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 £366
includes taxes & fees
1 Sept - 2 Sept
Bayfront Modern Retreat • Dock, Kayaks, Views

13. Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (11 reviews)
"conveniently located, very nice and cozy, loved it"
United States
Will C.
The price is £294
includes taxes & fees
3 Sept - 4 Sept
Oyster Oasis, Modern Loft in Historic Downtown

14. 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 £267
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Downtown: Tranquil Abode in Chincoteague!

15. 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 £304
includes taxes & fees
30 Aug - 31 Aug
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

16. Beautifully Renovated Cottage

Beautifully Renovated Cottage
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (12 reviews)
"Great renovation with open downstairs design and upstairs rain shower was a big hit. Minutes away from beach and downtown!! Will definitely stay again."
United States
Wayland A.
The price is £501
includes taxes & fees
15 Sept - 16 Sept
Beautifully Renovated Cottage

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. Crab Crib Loft in Historic Downtown Cape Charles

Crab Crib Loft in Historic Downtown Cape Charles
Historic Downtown Cape Charles
9.6 out of 10, Exceptional, (7 reviews)
"Excellent accommodations, cleanliness, communication, and location. Highly recommended!"
United States
Aaron L.
The price is £306
includes taxes & fees
1 Sept - 2 Sept
Crab Crib Loft in Historic Downtown Cape Charles

19. NEW! Family Friendly-Outdoor Shower-Fire Pit-Grill, Walk 2 Beach & Central Park!

NEW! Family Friendly-Outdoor Shower-Fire Pit-Grill, Walk 2 Beach & Central Park!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable close to the beach and downtown. It was the perfect location. We had a lovely time at the beach and strolling through the shops. Great for a 3 day getaway"
United States
Doreen G.
The price is £350
includes taxes & fees
8 Sept - 9 Sept
NEW! Family Friendly-Outdoor Shower-Fire Pit-Grill, Walk 2 Beach & Central Park!

20. Salt Box, One Block to the Beach

Salt Box, One Block to the Beach
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (23 reviews)
"This lovely home was conveniently located a block from the beach and two blocks from the shops. Anna was a wonderful host and we would definitely come back!"
United States
Sharon L.
The price is £351
includes taxes & fees
2 Sept - 3 Sept
Salt Box, One Block to the Beach
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

Everything you need to know about Eastern Shore of Virginia 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 Eastern Shore of Virginia 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 Eastern Shore of Virginia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Eastern Shore of Virginia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastern Shore of Virginia. 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 Eastern Shore of Virginia 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 Eastern Shore of Virginia holiday rentals we have selected for you start as low as £152 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Eastern Shore of Virginia rentals

At Expedia, we put the best Eastern Shore of Virginia 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 Eastern Shore of Virginia 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 Eastern Shore of Virginia 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 Eastern Shore of Virginia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.