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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, (674 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is NZ$232
includes taxes & fees
13 Dec - 14 Dec
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 NZ$575
includes taxes & fees
14 Nov - 15 Nov
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

3. The Harbour - Short Stays on Market

The Harbour - Short Stays on Market
Onancock
9.8 out of 10, Exceptional, (8 reviews)
"The Harbour on Market in Onancock, VA was a gorgeous condo and we will absolutely love to vacation here again in the future. Everything was top notch and the amenities surpassed our expectations. We had an unfortunate incident beyond anyone’s control and needed to vacate sooner than expected; however, the owners were so amazing and accommodated our needs. We highly recommend this place! 5 FULL STARS!"
United States
Jennifer M.
The price is NZ$409
includes taxes & fees
18 Nov - 19 Nov
The Harbour - Short Stays on Market

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)
"Exactly as it looks in the photos, comfortable, clean, generously stocked and thoughtfully curated. We will absolutely stay here again if we drive this route in the future!"
United States
Rhiannon L.
The price is NZ$526
includes taxes & fees
21 Nov - 22 Nov
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

5. Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!

Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!
Cape Charles
The price is NZ$921
includes taxes & fees
18 Nov - 19 Nov
Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!

6. Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (16 reviews)
"First time in Cape Charles! Our stay was perfect, great location and wonderful amenities!!"
United States
Julia G.
The price is NZ$742
includes taxes & fees
22 Nov - 23 Nov
Oyster Oasis, Modern Loft in Historic Downtown

7. 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$844
includes taxes & fees
16 Nov - 17 Nov
Cape Haven - Condo 1.5 Blocks from Beach

8. Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!

Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!
Historic Downtown Cape Charles
The price is NZ$626
includes taxes & fees
6 Dec - 7 Dec
Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!

9. Angler’s Dream: Oyster VA Farmhouse w/ Water Views, Boat Ramp & Outdoor Shower

Angler’s Dream: Oyster VA Farmhouse w/ Water Views, Boat Ramp & Outdoor Shower
Oyster
The price is NZ$659
includes taxes & fees
18 Nov - 19 Nov
Angler’s Dream: Oyster VA Farmhouse w/ Water Views, Boat Ramp & Outdoor Shower

10. 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, (8 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 NZ$632
includes taxes & fees
15 Nov - 16 Nov
NEW! Family Friendly-Outdoor Shower-Fire Pit-Grill, Walk 2 Beach & Central Park!

11. 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$540
includes taxes & fees
16 Nov - 17 Nov
The Waverly Tree House

12. Walk to Dining, Beach & Park~Family Friendly Home!

Walk to Dining, Beach & Park~Family Friendly Home!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (9 reviews)
"The close proximity to the park was perfect for our children and walking our dog"
United States
Jeff
The price is NZ$561
includes taxes & fees
17 Nov - 18 Nov
Walk to Dining, Beach & Park~Family Friendly Home!

13. First Floor King Suite~ Family Friendly~ Games +Loft! Play by the Bay!

First Floor King Suite~ Family Friendly~ Games +Loft! Play by the Bay!
Tower Hill
The price is NZ$694
includes taxes & fees
18 Nov - 19 Nov
First Floor King Suite~ Family Friendly~ Games +Loft! Play by the Bay!

14. Oyster Harbor Cottage – Where the Only Limit Is Your Imagination

Oyster Harbor Cottage – Where the Only Limit Is Your Imagination
Oyster
9.0 out of 10, Wonderful, (2 reviews)
"Great quiet neighborhood was awesome to be able to bring a boat there and not have to worry about it. "
United States
Jacob W.
Oyster Harbor Cottage – Where the Only Limit Is Your Imagination

15. Crab Crib Loft in Historic Downtown Cape Charles

Crab Crib Loft in Historic Downtown Cape Charles
Historic Downtown Cape Charles
9.2 out of 10, Wonderful, (15 reviews)
"Great little place just off Main Street. Super close to Resturants and a block from the water. Perfect for a couples getaway"
United States
Patrick S.
The price is NZ$742
includes taxes & fees
22 Nov - 23 Nov
Crab Crib Loft in Historic Downtown Cape Charles

16. Palm Villa

Palm Villa
Piney Island
9.2 out of 10, Wonderful, (5 reviews)
"The property was exactly as advertised and met our expectations. The manager was very nice. We would have preferred check-in instructions ahead of time without needing to call, but did not have any problems with check-in or our stay. We enjoyed the location and close proximity to shops, restaurants, and the Chincoteague Wildlife Refuge. We would stay here again."
United States
Scott D.
The price is NZ$332
includes taxes & fees
29 Nov - 30 Nov
Palm Villa

17. Marvelous Farm house style with 3-bedrooms in charming Cape Charles

Marvelous Farm house style with 3-bedrooms in charming Cape Charles
Cape Charles
Marvelous Farm house style with 3-bedrooms in charming Cape Charles

18. New! By Park-Family Friendly-Fenced Yard-Fire Pit! Walk to Central Park & Beach!

New! By Park-Family Friendly-Fenced Yard-Fire Pit! Walk to Central Park & Beach!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay and cute cottage and location"
United States
Elsie W.
The price is NZ$709
includes taxes & fees
18 Nov - 19 Nov
New! By Park-Family Friendly-Fenced Yard-Fire Pit! Walk to Central Park & Beach!

19. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.2 out of 10, Wonderful, (27 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
The price is NZ$751
includes taxes & fees
22 Nov - 23 Nov
Smith Beach cottage w/ private sunset

20. 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, (87 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is NZ$485
includes taxes & fees
1 Dec - 2 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
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.