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Holiday Rentals in Eastern Shore of Virginia

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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, (644 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is €197
includes taxes & fees
18 Oct - 19 Oct
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (328 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is €198
includes taxes & fees
23 Sept - 24 Sept
Blufin Bungalows & Marina

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, (28 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is €271
includes taxes & fees
22 Sept - 23 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

4. 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 €305
includes taxes & fees
29 Sept - 30 Sept
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

5. The Glick - Short Stays on Market

The Glick - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
The price is €217
includes taxes & fees
22 Sept - 23 Sept
The Glick - 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, (23 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
The price is €385
includes taxes & fees
27 Sept - 28 Sept
Smith Beach cottage w/ private sunset

7. 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 €322
includes taxes & fees
22 Sept - 23 Sept
The Waverly Tree House

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, (76 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
The price is €317
includes taxes & fees
24 Sept - 25 Sept
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

9. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (75 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
The price is €445
includes taxes & fees
7 Oct - 8 Oct
Nassawadox Creek Waterfront Home with Private Pool

10. 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, (140 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.
As close as you can get to the ocean south of Chincoteague

11. 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 €493
includes taxes & fees
22 Sept - 23 Sept
Cape Haven - Condo 1.5 Blocks from Beach

12. 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 €479
includes taxes & fees
22 Sept - 23 Sept
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

13. 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 €509
includes taxes & fees
23 Sept - 24 Sept
Beautifully Renovated Cottage

14. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 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 €173
includes taxes & fees
6 Oct - 7 Oct
Assateageue Inn 104 by Seaside Vacations & Sales

15. 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 €169
includes taxes & fees
23 Sept - 24 Sept
Assateague Inn 111 by Seaside Vacations & Sales

16. 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 €398
includes taxes & fees
21 Oct - 22 Oct
Salt Box, One Block to the Beach

17. 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 €495
includes taxes & fees
14 Oct - 15 Oct
Park Place - Comfy Condo Close to Beach

18. 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 €352
includes taxes & fees
26 Sept - 27 Sept
2 Mi to Downtown: Tranquil Abode in Chincoteague!

19. The Lilliston - Short Stays on Market

The Lilliston - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable , nice interior design, great location , lovely unit"
United States
Sena B.
The price is €224
includes taxes & fees
22 Sept - 23 Sept
The Lilliston - Short Stays on Market
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 €197 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.