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Eastern Shore of Virginia Vacation Rentals

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Our top choices for Eastern Shore of Virginia vacation rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (599 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is CA $430
CA $483 total
includes taxes & fees
Aug 18 - Aug 19
Key West Cottages

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, (21 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 $213
CA $497 total
includes taxes & fees
Jul 22 - Jul 23
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

The Captains Quarters located in Cape Charles, VA offers breathtaking views.

The Captains Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles
9.8 out of 10, Exceptional, (61 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
The price is CA $351
CA $502 total
includes taxes & fees
Aug 12 - Aug 13
The Captains Quarters located in Cape Charles, VA offers breathtaking views.

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, (26 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is CA $213
CA $444 total
includes taxes & fees
Jul 22 - Jul 23
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

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, (12 reviews)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
United States
William M.
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (30 reviews)
"Had a great stay! Place was very clean and host was great a communication."
United States
Jen G.
Assateageue Inn 104 by Seaside Vacations & Sales

The Social - Short Stays on Market

The Social - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (2 reviews)
"Loved every thing about the rental, the furniture was trendy and comfy. The unit was also spacious and clean. We enjoyed walking to the harbor and window shopping thru town. Also, had an awesome lunch across the street and even went back for dinner."
United States
Karen S.
The price is CA $188
CA $402 total
includes taxes & fees
Jul 21 - Jul 22
The Social - Short Stays on Market

Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (9 reviews)
"Clean, well-decorated space. Close to beach access, shopping & dining. Parking is on-street only. Agents were responsive when questions were asked. Would stay again."
United States
Sara
The price is CA $310
CA $605 total
includes taxes & fees
Jul 29 - Jul 30
Oyster Oasis, Modern Loft in Historic Downtown

Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.8 out of 10, Exceptional, (8 reviews)
"The booking was fast and easy. When we got there the place was very clean and organized. I would totally recommend this location to friends and loved ones. We had a wonderful time there. The whole experience was great from booking to leaving."
United States
Jessika S.
The price is CA $286
CA $698 total
includes taxes & fees
Aug 9 - Aug 10
Smith Beach cottage w/ private sunset

Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Everything was as it was stated. Clean, neat and stocked with essentials. Cozy and comfortable. Quiet and peaceful. Loved the island and will be coming back. "
United States
Kera S.
Assateague Inn 213 by Seaside Vacations & Sales

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, (46 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $335
CA $795 total
includes taxes & fees
Aug 13 - Aug 14
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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 CA $508
CA $650 total
includes taxes & fees
Jul 22 - Jul 23
Tiny House Hideaway with King sized Bed

Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (3 reviews)
"Very nice and well designed property. As soon as you open the door, you can tell that a lot of love and dedication came into designing this beautiful little cottage.Done with taste. Well located, away from the busy beach town center, yet very close to the main street (Maddox Street) and to the National Park where the beach is located.It will be our to-go-to place in the Island."
United States
Jean-Charles G.
The price is CA $283
CA $499 total
includes taxes & fees
Aug 17 - Aug 18
Cozy 2-bedroom house in Chincoteague

Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views

Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views
Wachapreague
10.0 out of 10, Exceptional, (3 reviews)
"Cozy , comfortable, clean and all the amenities one would need. Wonderful helpful hosts. Wachapreague General Store just across the street with coffee and breakfast sandwiches that were out of this world. If you find yourself in need of a place to decompress The Artist Apartment in Wachapreague is certainly your destination."
United States
Frank W.
The price is CA $420
CA $779 total
includes taxes & fees
Aug 2 - Aug 3
Artist Apartment | Renovated Wachapreague Condo Above Art Gallery w/ Rooftop Deck & Sunset Views

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (62 reviews)
"This is a great property with a great view of the bay. It's tucked away in a quiet little neighborhood in a nice and friendly community. Chincoteague is close by and it's not too far from Assateague. The property management team is excellent. They were extremely responsive to our questions and requests. They were patient with all our questions. Kelly was fantastic. The best hosts I've had."
United States
A Shabeen J.
The price is CA $245
CA $664 total
includes taxes & fees
Aug 8 - Aug 9
The purple door at the bay.

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (138 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is CA $445
CA $750 total
includes taxes & fees
Jul 21 - Jul 22
Pet-friendly creekside cottage w/ backyard

Experience Tiny Living, in Cape Charles, Va

Experience Tiny Living, in Cape Charles, Va
Cape Charles
10.0 out of 10, Exceptional, (2 reviews)
"Exactly what listing said! Was super clean and perfect for our short trip! Easy drive to and from the beach and the town of Cape Charles"
United States
Ella D.
The price is CA $443
CA $567 total
includes taxes & fees
Jul 22 - Jul 23
Experience Tiny Living, in Cape Charles, Va

Whimsical Tiny House, Cape Charles Virginia

Whimsical Tiny House, Cape Charles Virginia
Cape Charles
9.2 out of 10, Wonderful, (14 reviews)
"We love staying in the tiny home, Eric was such a nice host"
United States
Cathy W.
The price is CA $508
CA $650 total
includes taxes & fees
Jul 20 - Jul 21
Whimsical Tiny House, Cape Charles Virginia

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, (5 reviews)
"Excellent accommodations, cleanliness, communication, and location. Highly recommended!"
United States
Aaron L.
The price is CA $284
CA $570 total
includes taxes & fees
Jul 21 - Jul 22
Crab Crib Loft in Historic Downtown Cape Charles

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 $443
CA $565 total
includes taxes & fees
Jul 19 - Jul 20
Tiny House close to the Beaches of Cape Charles
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.