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

Eastern Shore of Virginia Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (641 reviews)
"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"
United States
LaTonya
The price is CA $282
CA $317 total
includes taxes & fees
Oct 18 - Oct 19
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (327 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is CA $196
CA $298 total
includes taxes & fees
Sep 23 - Sep 24
Blufin Bungalows & Marina

3. 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 $222
CA $245 total
includes taxes & fees
Sep 24 - Sep 25
Virginia Landing RV Campground

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 $213
CA $417 total
includes taxes & fees
Sep 20 - Sep 21
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

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.
The price is CA $213
CA $489 total
includes taxes & fees
Sep 30 - Oct 1
Newly Constructed Modern 1 Bedroom Apartment with Luxury Shower ~ Sleeps 3

6. The Glick - Short Stays on Market

The Glick - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $104
CA $320 total
includes taxes & fees
Sep 22 - Sep 23
The Glick - Short Stays on Market

7. 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 CA $220
CA $614 total
includes taxes & fees
Sep 27 - Sep 28
Smith Beach cottage w/ private sunset

8. 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 $308
CA $520 total
includes taxes & fees
Sep 21 - Sep 22
The Waverly Tree House

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
The price is CA $350
CA $497 total
includes taxes & fees
Sep 20 - Sep 21
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

10. 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 CA $308
CA $704 total
includes taxes & fees
Oct 7 - Oct 8
Nassawadox Creek Waterfront Home with Private Pool

11. 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, (139 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

12. 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 $201
CA $777 total
includes taxes & fees
Sep 21 - Sep 22
Cape Haven - Condo 1.5 Blocks from Beach

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.
The price is CA $272
CA $768 total
includes taxes & fees
Sep 22 - Sep 23
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

14. 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 $203
CA $805 total
includes taxes & fees
Sep 23 - Sep 24
Beautifully Renovated Cottage

15. 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 CA $142
CA $268 total
includes taxes & fees
Sep 21 - Sep 22
Assateageue Inn 104 by Seaside Vacations & Sales

16. 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 CA $142
CA $268 total
includes taxes & fees
Sep 21 - Sep 22
Assateague Inn 111 by Seaside Vacations & Sales

17. 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 CA $248
CA $607 total
includes taxes & fees
Sep 28 - Sep 29
Salt Box, One Block to the Beach

18. 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 CA $168
CA $810 total
includes taxes & fees
Oct 14 - Oct 15
Park Place - Comfy Condo Close to Beach

19. 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 CA $221
CA $565 total
includes taxes & fees
Sep 26 - Sep 27
2 Mi to Downtown: Tranquil Abode in Chincoteague!

20. The Lilliston - Short Stays on Market

The Lilliston - Short Stays on Market
Onancock
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $125
CA $346 total
includes taxes & fees
Sep 22 - Sep 23
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.
Save an average of 15% on thousands of hotels when you're signed in

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.