Eastern Shore Vacation Homes

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

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Our top choices for Eastern Shore holiday homes

A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

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

Stevensville

Michael V.

HK$2,528 total

includes taxes & fees

2 Nov - 3 Nov

A brick building with a white porch and a well-maintained lawn.

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

Cambridge

Mary Beth S.

HK$3,043 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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

Stevensville

Anthony P.

HK$2,286 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a wooden table set for four, surrounded by wicker chairs.

4. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

North Ocean City

Nicole G.

HK$2,310 total

includes taxes & fees

1 Nov - 2 Nov

A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,476 total

includes taxes & fees

29 Oct - 30 Oct

A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

6. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

North Ocean City

Mike G.

HK$2,398 total

includes taxes & fees

2 Nov - 3 Nov

A marina with boats docked, a water tower, and residential buildings with balconies.

7. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Cambridge

mike

HK$3,918 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with wooden cabinets, a dining area set for six, and a large window providing natural light.

8. BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

North Ocean City

holly s.

HK$2,547 total

includes taxes & fees

28 Oct - 29 Oct

A dining area with a wooden table and chairs, a ceiling fan, and large windows with blinds.

9. Beach Paradise 105 - Beach Home at Broad Marsh OC

North Ocean City

renee d.

HK$2,336 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a dining area with white chairs and a wooden table.

10. Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Downtown Ocean City

Olivia R.

HK$2,398 total

includes taxes & fees

1 Nov - 2 Nov

A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

11. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

HK$2,245 total

includes taxes & fees

2 Nov - 3 Nov

A spacious living room with a grey sectional sofa, wooden flooring, a staircase, and a kitchen in the background.

12. Sands of Tide

North Ocean City

HK$3,795 total

includes taxes & fees

1 Nov - 2 Nov

A single-story house with a front porch, a door, and a mailbox.

13. Salisbury Hideaway

Salisbury

Michelle S.

HK$2,552 total

includes taxes & fees

28 Oct - 29 Oct

A kitchen with wooden cabinets, a dining table, and a refrigerator.

14. Family Retreat at Lansdowne Manor

Centreville

Emily C.

HK$2,251 total

includes taxes & fees

1 Nov - 2 Nov

A house surrounded by dense trees and a wooden dock extending into a body of water.

15. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Newark

David M.

HK$3,239 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

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

Elkton

Shana G.

HK$3,027 total

includes taxes & fees

2 Nov - 3 Nov

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

17. Cottage near the Bay

Crisfield

Karen J.

HK$1,463 total

includes taxes & fees

28 Oct - 29 Oct

A grassy area with a wooden dock extending into a calm body of water, surrounded by trees and greenery.

18. Waterfront Getaway with Dock

Woolford

Meagan G.

HK$1,954 total

includes taxes & fees

1 Nov - 2 Nov

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

Port Deposit

Don S.

HK$1,541 total

includes taxes & fees

28 Oct - 29 Oct

A covered outdoor seating area with a wooden ceiling, two chairs, a table, and a wicker sofa.

20. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Betterton

HK$2,937 total

includes taxes & fees

23 Nov - 24 Nov

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Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent

"Wish the indoor pool could have been a little warmer."

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

8/10 Good

"The property lived up to the Marriot standards in terms of cleanliness and decor. our room was clean. The floors were clean. The staff we encountered at check in/out and dining were very polite. The beach view from our room was awesome! Beach view from common areas were also amazing. On the day of check out there was a water shut off maintenance for the day. We were not significantly affected as that was out check out day. The staff offered alternate perks to affected guests. This was our first visit. We were impressed with the property and plan to return with the hope of enjoying more of the property offering."

Princess Royale Oceanfront Resort

10/10 Excellent

"I truly enjoyed my stay. The room was clean and inviting. After attending the Sunfest and Wine on the Beach I relaxed in the pool area with an amazing cocktail. The staff were amazing from the nice young lady who checked me in to the gentleman that helped with my luggage to the inviting barista who made the best pumpkin spice latte. The hotel also had a festive Halloween display. Hotel staff participated in a pumpkin carving contest. Guests vote for the most creative display. This showed team work and comradery which leads to great customer experience. Princess Royale will be my go to hotel when visiting Ocean City. Highly recommend!"

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