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Eastern Shore of Virginia Vacation Rentals

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Our top choices for Eastern Shore of Virginia vacation rentals

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (662 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $271
CA $304 total
includes taxes & fees
Nov 19 - Nov 20
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 CA $224
CA $247 total
includes taxes & fees
Oct 28 - Oct 29
Virginia Landing RV Campground

3. 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 CA $215
CA $503 total
includes taxes & fees
Oct 26 - Oct 27
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

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 CA $215
CA $448 total
includes taxes & fees
Oct 26 - Oct 27
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

5. The Lilliston - Short Stays on Market

The Lilliston - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (6 reviews)
"This was a wonderful, large and beautiful accommodation. It was quite the surprise to find in such an exceptional bayside harbor town. Everything was incredibly clean and modern and comfortable."
United States
Jacob P.
The price is CA $119
CA $341 total
includes taxes & fees
Oct 21 - Oct 22
The Lilliston - Short Stays on Market

6. 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 CA $283
CA $496 total
includes taxes & fees
Oct 21 - Oct 22
The Waverly Tree House

7. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (24 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
The price is CA $222
CA $626 total
includes taxes & fees
Nov 2 - Nov 3
Smith Beach cottage w/ private sunset

8. 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 CA $138
CA $708 total
includes taxes & fees
Oct 21 - Oct 22
Cape Haven - Condo 1.5 Blocks from Beach

9. 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 CA $344
CA $441 total
includes taxes & fees
Oct 21 - Oct 22
Tiny House close to the Beaches of Cape Charles

10. Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (15 reviews)
"conveniently located, very nice and cozy, loved it"
United States
Will C.
The price is CA $312
CA $608 total
includes taxes & fees
Nov 2 - Nov 3
Oyster Oasis, Modern Loft in Historic Downtown

11. 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 CA $115
CA $752 total
includes taxes & fees
Oct 21 - Oct 22
Beautifully Renovated Cottage

12. 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, (82 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
The price is CA $353
CA $505 total
includes taxes & fees
Oct 27 - Oct 28
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

13. 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, (14 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 CA $312
CA $608 total
includes taxes & fees
Nov 2 - Nov 3
Crab Crib Loft in Historic Downtown Cape Charles

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

Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!
Cape Charles
The price is CA $180
CA $232 total
includes taxes & fees
Nov 2 - Nov 3
Family Getaway~ Game/Bunk Room~ King Bed~ Firepit!

15. Walk 2 Beach & Restaurants~Central Park~ King Bed!

Walk 2 Beach & Restaurants~Central Park~ King Bed!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (12 reviews)
"We really enjoyed this spot and look forward to returning! The hosts were very responsive and nearby should something come up. When we arrived there were items for us from the local bakery and the house is was stocked in a thoughtful way which allows you to pack lightly. Park proximity and a short beach walk was perfect. Sets a high bar for a pet friendly stay!"
United States
Alex and Celena M.
The price is CA $182
CA $523 total
includes taxes & fees
Oct 25 - Oct 26
Walk 2 Beach & Restaurants~Central Park~ King Bed!

16. Restored 1930’s Tiny Home 3 min to Cape Charles

Restored 1930’s Tiny Home 3 min to Cape Charles
Cape Charles
10.0 out of 10, Exceptional, (1 review)
"Loved this small vacation village of tiny houses for a weekend getaway!"
United States
Kevin B.
The price is CA $299
CA $384 total
includes taxes & fees
Oct 21 - Oct 22
Restored 1930’s Tiny Home 3 min to Cape Charles

17. 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, (7 reviews)
"The close proximity to the park was perfect for our children and walking our dog"
United States
Jeff
The price is CA $174
CA $512 total
includes taxes & fees
Oct 22 - Oct 23
Walk to Dining, Beach & Park~Family Friendly Home!

18. 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, (83 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $185
CA $438 total
includes taxes & fees
Oct 27 - Oct 28
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

19. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (77 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
The price is CA $273
CA $662 total
includes taxes & fees
Nov 2 - Nov 3
Nassawadox Creek Waterfront Home with Private Pool

20. 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 CA $141
CA $550 total
includes taxes & fees
Oct 21 - Oct 22
NEW! Family Friendly-Outdoor Shower-Fire Pit-Grill, Walk 2 Beach & Central Park!
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.