A marina with numerous boats docked at wooden piers under a clear sky.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Eastern Shore holiday homes

Exterior

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (54 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$1,098
HK$2,706 total
includes taxes & fees
2 Sept - 3 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is HK$1,133
HK$2,687 total
includes taxes & fees
1 Sept - 2 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Living area

3. Cozy 1-bedroom house in lovely Chestertown with AC

Cozy 1-bedroom house in lovely Chestertown with AC
Chestertown
The price is HK$1,482
HK$2,270 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 1-bedroom house in lovely Chestertown with AC
Interior

4. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (59 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is HK$635
HK$1,479 total
includes taxes & fees
2 Sept - 3 Sept
Cottage near the Bay
Exterior detail

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is HK$1,569
HK$2,476 total
includes taxes & fees
24 Aug - 25 Aug
BAYSIDE BUNGALOW
Marina

6. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$2,196
HK$4,057 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Smart TV

7. Spacious canal-front home with private dock, parking, and family-friendly amenities.

Spacious canal-front home with private dock, parking, and family-friendly amenities.
Ocean Pines
10.0 out of 10, Exceptional, (2 reviews)
"The home was beautiful, very clean and spacious. The back deck had a beautiful view of the canal and was very peaceful. Check in and out process was very easy. Owner was very communicative before, during and after our stay answering any questions I had. Location was perfect, just about 10 minutes from Ocean City, close to the beach and boardwalk. We very much enjoyed our stay here and would definitely return !"
United States
Alyssa L.
The price is HK$1,486
HK$8,990 total
includes taxes & fees
24 Aug - 25 Aug
Spacious canal-front home with private dock, parking, and family-friendly amenities.
Coffee/tea maker, fridge, microwave, oven

8. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is HK$1,051
HK$2,100 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Barn Loft: Country Views & Central to Beaches
Coffee/tea maker, fridge, microwave, oven

9. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is HK$1,172
HK$2,847 total
includes taxes & fees
25 Aug - 26 Aug
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Dining

10. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is HK$1,960
HK$3,324 total
includes taxes & fees
24 Aug - 25 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Coffee/tea maker, fridge, microwave, oven

11. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is HK$1,804
HK$2,187 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Getaway with Dock
Outdoor dining

12. 6 Mi to Salisbury: Forest-View Sanctuary!

6 Mi to Salisbury: Forest-View Sanctuary!
Parsonsburg
9.8 out of 10, Exceptional, (6 reviews)
"Awesome place "
United States
Rebecca M.
The price is HK$729
HK$2,164 total
includes taxes & fees
24 Aug - 25 Aug
6 Mi to Salisbury: Forest-View Sanctuary!
Exterior

13. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is HK$1,011
HK$2,601 total
includes taxes & fees
21 Sept - 22 Sept
Salisbury Hideaway
Exterior

14. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,746
HK$2,911 total
includes taxes & fees
24 Aug - 25 Aug
Bohemia Manor Farm
Beach

15. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$862
HK$1,920 total
includes taxes & fees
21 Sept - 22 Sept
Tangier Escape, great place get away from it all on Deal Island, MD.
Outdoor dining

16. BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (110 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is HK$1,568
HK$3,012 total
includes taxes & fees
21 Sept - 22 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Outdoor dining

17. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (2 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is HK$1,294
HK$1,485 total
includes taxes & fees
22 Sept - 23 Sept
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Exterior

18. Pool, Trail Access! Dog-Friendly Ocean Pines Haven

Pool, Trail Access! Dog-Friendly Ocean Pines Haven
Ocean Pines
9.6 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay and the house was perfect for our family and my kids loved it. "
United States
Vannessa H.
The price is HK$1,035
HK$3,505 total
includes taxes & fees
27 Aug - 28 Aug
Pool, Trail Access! Dog-Friendly Ocean Pines Haven
Interior

19. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is HK$2,996
HK$3,700 total
includes taxes & fees
15 Sept - 16 Sept
Family Retreat at Lansdowne Manor
Marina

20. Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is HK$1,764
HK$2,821 total
includes taxes & fees
21 Sept - 22 Sept
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
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 Hotel Reviews

Howard Johnson by Wyndham Ocean City Oceanfront

Howard Johnson by Wyndham Ocean City Oceanfront

8/10 Good
"Room was clean and staff were super helpful and friendly. Room was a bit small and bathroom was no bigger than closet, but it was stocked well. Biggest complaint was that housekeeping skipped our room every single day even though we were out of the room by 10 am. Instead we would get a call or text from the hotel later in the day asking if we needed anything. I appreciated them checking with us, but it would have been nicer to just have the room ready. Pool was decent, beach towels available poolside. Parking lot was not big enough for number of spaces especially when people had bike carriers or trailer hitches. Overall stay was great."
Paul 4-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Vacation Homes information

Number of reviews
489
Accommodation
480 Vacation Homes
Lowest Price
HK$1,479
Highest Price
HK$8,990

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