A beach with waves crashing onto the shore and a person walking along the beach.

Eastern Shore of Virginia Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Eastern Shore of Virginia vacation rentals

1. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (324 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
$181 nightly
The price is $203
Sep 23 - Sep 24
Total with taxes and fees
Blufin Bungalows & Marina
A waterfront house with a balcony, dock, and a view of the water.

2. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (639 reviews)
"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"
United States
LaTonya
$224 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Key West Cottages
A modern kitchen with a stainless steel refrigerator, a dark wall with framed artwork, and a brick wall with a hanging light fixture.

3. The Lilliston - Short Stays on Market

The Lilliston - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
$226 nightly
The price is $250
Sep 22 - Sep 23
Total with taxes and fees
The Lilliston - Short Stays on Market
A staircase with a dark door at the bottom and a light fixture above it.

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.
$288 nightly
The price is $318
Sep 19 - Sep 20
Total with taxes and fees
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
A two-story house with a front porch, a number '23314' on the door, and a small front yard.

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.
$323 nightly
The price is $356
Sep 29 - Sep 30
Total with taxes and fees
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

6. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.6 out of 10, Exceptional, (22 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
$381 nightly
The price is $444
Sep 20 - Sep 21
Total with taxes and fees
Smith Beach cottage w/ private sunset
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

7. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$359 nightly
The price is $403
Sep 26 - Sep 27
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

8. 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
$184 nightly
The price is $192
Sep 21 - Sep 22
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
A covered deck with wooden chairs and tables, overlooking a marina with boats.

9. 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, (75 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
$315 nightly
The price is $358
Sep 20 - Sep 21
Total with taxes and fees
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
A covered patio with a wooden ceiling, a table with chairs, and a view of a backyard with a grill and greenery.

10. Golf cart included! 5 blocks to the beach, and in historic district!

Golf cart included! 5 blocks to the beach, and in historic district!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (16 reviews)
"We loved everything about this house. Can’t wait to book it again for next year!"
United States
Steven F.
$595 nightly
The price is $672
Sep 26 - Sep 27
Total with taxes and fees
Golf cart included! 5 blocks to the beach, and in historic district!
A two-story house with a covered porch, a front door, and a small front yard.

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.
$523 nightly
The price is $592
Sep 23 - Sep 24
Total with taxes and fees
Beautifully Renovated Cottage
A wooden deck with a chair, a welcome mat, and a view of a forest.

12. 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.
$353 nightly
The price is $393
Sep 21 - Sep 22
Total with taxes and fees
The Waverly Tree House
A living room with a light blue wall, a wooden coffee table, a beige sofa with blue cushions, a wicker chair, and a patterned rug.

13. 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.
$485 nightly
The price is $549
Sep 22 - Sep 23
Total with taxes and fees
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
A wooden boardwalk leading to a beach with a sunset view.

14. 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.
$400 nightly
The price is $432
Sep 28 - Sep 29
Total with taxes and fees
Salt Box, One Block to the Beach
A house surrounded by dense greenery and a small dock extending into a body of water.

15. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (74 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
$447 nightly
The price is $497
Oct 7 - Oct 8
Total with taxes and fees
Nassawadox Creek Waterfront Home with Private Pool
A wooden boardwalk leading to a beach with a pier in the background.

16. 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.
$515 nightly
The price is $573
Oct 14 - Oct 15
Total with taxes and fees
Park Place - Comfy Condo Close to Beach
A two-story building with a central entrance and a wooden walkway leading to it.

17. Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Lauren P.
$184 nightly
The price is $192
Sep 27 - Sep 28
Total with taxes and fees
Assateague Inn 213 by Seaside Vacations & Sales
A covered porch with wicker chairs and a view of the outdoors.

18. 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
$312 nightly
The price is $339
Oct 1 - Oct 2
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A sandy beach with footprints and a person walking.

19. 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.
$356 nightly
The price is $400
Oct 3 - Oct 4
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A two-story house with a porch, white railings, and a front door.

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, (6 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.
$343 nightly
The price is $389
Oct 7 - Oct 8
Total with taxes and fees
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

Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

10/10 Excellent
"This is my third stay in this gorgeous hotel, conveniently located on main street within easy walking distance of cafés, bars and restaurants. Contemporary decor, huge rooms, well maintained grounds. I love that there is both an indoor and an outdoor pool. The views over the bay are just magical. You can swing in a hammock by the dock, admire the sunset or just chill in one of their many outdoor lounge areas. The breakfast is quite good with a choice of eggs, bacon, fresh waffles, fruits, yogurt, pastries and bread. And coffee, of course! Staff is very friendly and helpful. Can't wait to return!"
Celine 1-night trip
Posted 10 hours ago
Comfort Suites Chincoteague Island Bayfront Resort

Find out more about Eastern Shore of Virginia

Everything you need to know about Eastern Shore of Virginia vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore of Virginia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Shore of Virginia vacation 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 low season months. For more hustle and bustle, you may prefer to visit Eastern Shore of Virginia in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $203 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

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