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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, (648 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is NZ$400
includes taxes & fees
18 Oct - 19 Oct
Key West Cottages

2. Virginia Landing RV Campground

Virginia Landing RV Campground
2.0 star property
Quinby
8.0 out of 10, Very good, (38 reviews)
"If you’re looking for a resort atmosphere, this isn’t it—and that’s exactly the point. If you want a beautiful, peaceful place to reset, unplug, and escape for a while, you’ve just hit the jackpot. Every second of our stay was perfect. I read all of the reviews beforehand, so I knew what to expect and came prepared. It was everything I hoped it would be and more. We will absolutely be back—without a single doubt."
United States
Nicole
The price is NZ$310
includes taxes & fees
29 Sept - 30 Sept
Virginia Landing RV Campground

3. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (331 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is NZ$401
includes taxes & fees
13 Oct - 14 Oct
Blufin Bungalows & Marina

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 NZ$546
includes taxes & fees
9 Oct - 10 Oct
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

5. 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$608
includes taxes & fees
29 Sept - 30 Sept
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

6. The Glick - Short Stays on Market

The Glick - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$447
includes taxes & fees
29 Sept - 30 Sept
The Glick - Short Stays on Market

7. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (23 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
The price is NZ$773
includes taxes & fees
29 Sept - 30 Sept
Smith Beach cottage w/ private sunset

8. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
2 Mi to Downtown: Tranquil Abode in Chincoteague!

9. The Waverly Tree House

The Waverly Tree House
Machipongo
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and clean spot. Great quiet morning views of the creak. We enjoyed a relaxing stay. It had everything we needed. "
United States
Jeanna C.
The price is NZ$609
includes taxes & fees
29 Sept - 30 Sept
The Waverly Tree House

10. 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, (79 reviews)
"What a great location. In the heart of the harbor above the yacht club office. Close to the cute little village of Cape Charles. Quite charming really."
United States
Thomas
The price is NZ$616
includes taxes & fees
29 Sept - 30 Sept
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

11. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (76 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
The price is NZ$870
includes taxes & fees
7 Oct - 8 Oct
Nassawadox Creek Waterfront Home with Private Pool

12. 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 NZ$756
includes taxes & fees
30 Sept - 1 Oct
Salt Box, One Block to the Beach

13. Family-Friendly Fun Just 1 Block from Downtown Cape Charles

Family-Friendly Fun Just 1 Block from Downtown Cape Charles
Historic Downtown Cape Charles
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful home, tons of room! Had a great stay there!"
United States
Colleen B.
Family-Friendly Fun Just 1 Block from Downtown Cape Charles

14. 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$728
includes taxes & fees
29 Sept - 30 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

15. 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)
"Was wonderful..so close to everything..property was great ..had everything you need"
United States
Donna L.
The price is NZ$955
includes taxes & fees
6 Oct - 7 Oct
Cape Haven - Condo 1.5 Blocks from Beach

16. 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, (64 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 NZ$937
includes taxes & fees
29 Sept - 30 Sept
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

17. 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$579
includes taxes & fees
1 Oct - 2 Oct
Pet-friendly creekside cottage w/ backyard

18. 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$339
includes taxes & fees
30 Sept - 1 Oct
Assateague Inn 111 by Seaside Vacations & Sales

19. Beautifully Renovated Cottage

Beautifully Renovated Cottage
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (13 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 NZ$1,032
includes taxes & fees
29 Sept - 30 Sept
Beautifully Renovated Cottage

20. Tiny House Hideaway with King sized Bed

Tiny House Hideaway with King sized Bed
Cape Charles
9.6 out of 10, Exceptional, (5 reviews)
"We absolutely enjoyed our little tiny home! The property was great and the things to do close by were great! We would definitely stay again! "
United States
Leslie
The price is NZ$574
includes taxes & fees
5 Oct - 6 Oct
Tiny House Hideaway with King sized Bed
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.