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Our top choices for Eastern Shore vacation homes

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is ¥12,361
¥42,447 total
includes taxes & fees
Nov 10 - Nov 11
Charming Coastal/Country Home w/3 Acres & Sauna!

2. 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, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is ¥28,526
¥57,452 total
includes taxes & fees
Nov 30 - Dec 1
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is ¥42,790
¥49,221 total
includes taxes & fees
Nov 24 - Nov 25
Family Friendly Cozy 3 Bedroom Duplex

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

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ¥17,116
¥48,061 total
includes taxes & fees
Nov 15 - Nov 16
Relax on Kent Island in 4 Bedroom Home w/Waterview

5. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is ¥35,658
¥55,268 total
includes taxes & fees
Dec 1 - Dec 2
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

6. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ¥31,696
¥47,674 total
includes taxes & fees
Nov 10 - Nov 11
BAYSIDE BUNGALOW

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

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (165 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is ¥7,132
¥47,925 total
includes taxes & fees
Nov 10 - Nov 11
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

8. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is ¥22,821
¥44,181 total
includes taxes & fees
Nov 10 - Nov 11
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

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

Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
Downtown Ocean City
9.6 out of 10, Exceptional, (34 reviews)
"Great space, close to the beach, we had an amazing stay!"
United States
Olivia R.
The price is ¥7,132
¥47,925 total
includes taxes & fees
Nov 10 - Nov 11
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

10. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is ¥47,227
¥61,267 total
includes taxes & fees
Nov 11 - Nov 12
More, than just a place to sleep - welcome home!

11. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is ¥21,078
¥51,573 total
includes taxes & fees
Nov 30 - Dec 1
Salisbury Hideaway

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

Beach Paradise 105 - Beach Home at Broad Marsh OC
North Ocean City
9.8 out of 10, Exceptional, (14 reviews)
"Loved this property. It was clean and had everything we needed. Had a wonderful stay!! Highly recommend!"
United States
renee d.
The price is ¥6,181
¥46,682 total
includes taxes & fees
Nov 11 - Nov 12
Beach Paradise 105 - Beach Home at Broad Marsh OC

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

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is ¥38,493
¥77,918 total
includes taxes & fees
Nov 10 - Nov 11
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"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...
United States
Miriam G.
The price is ¥31,379
¥43,845 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

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

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is ¥28,241
¥55,137 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

16. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ¥45,384
¥78,849 total
includes taxes & fees
Dec 1 - Dec 2
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

17. 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 ¥14,739
¥41,373 total
includes taxes & fees
Nov 18 - Nov 19
6 Mi to Salisbury: Forest-View Sanctuary!

18. 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, (7 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is ¥27,956
¥58,359 total
includes taxes & fees
Nov 17 - Nov 18
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

19. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
The price is ¥40,845
¥75,717 total
includes taxes & fees
Nov 10 - Nov 11
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

20. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 ¥38,843
¥46,309 total
includes taxes & fees
Nov 10 - Nov 11
Family Retreat at Lansdowne Manor
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.

Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savor fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

A historic white mansion with a sign in front.

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