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726 places

Guest favorite

Condo in Betterton

Best kept secret beach-condo on the Chesapeake Bay

2 min walk

Apr 20 – 25

$255 per night

4.89 out of 5 average rating, 18 reviews

Home in Betterton

Bay Cliff: Vacation on the Eastern Shore

9 min walk

Apr 21 – 26

$1,500 per night

Guest favorite

Apartment in Worton

Elliott House Historic Home Near Chesapeake Bay

6 min drive

Apr 20 – 25

$159 per night

5.0 out of 5 average rating, 16 reviews

Superhost

Cottage in Betterton

Cottage By the Chesapeake

7 min walk

Apr 20 – 25

$140 per night

4.8 out of 5 average rating, 51 reviews

Guest favorite

Home in Betterton

Vast Vintage Victorian in Bayside Betterton

6 min walk

Apr 20 – 25

$495 per night

4.92 out of 5 average rating, 39 reviews

Guest favorite

Condo in Betterton

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

1 min walk

Apr 20 – 25

$295 per night

4.93 out of 5 average rating, 30 reviews

Home in Still Pond

Historic Farmhouse Getaway

7 min drive

Apr 20 – 25

$450 per night

New place to stay

Guest favorite

Home in Rock Hall

Chesapeake Bay Retreat w/ Views!

46 min drive

May 12 – 17

$139 per night, originally $250

5.0 out of 5 average rating, 16 reviews

Guest favorite

Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

21 min drive

Apr 28 – May 3

$237 per night

4.94 out of 5 average rating, 64 reviews

Guest favorite

Cottage in Betterton

Charming Home w/Great Porch, Overlooking the Bay

6 min walk

Apr 20 – 25

$325 per night

5.0 out of 5 average rating, 18 reviews

Guest favorite

Cottage in Earleville

The Cottage at Crystal

26 min drive

Apr 23 – 28

$150 per night

4.94 out of 5 average rating, 35 reviews

Apartment in Worton

Waterfront Retreat with Private Dock and Beach

17 min drive

Apr 29 – May 4

$210 per night

New place to stay

Home in Worton

Still Pond Creek Headwaters Hideaway

10 min drive

Apr 21 – 26

$221 per night

Guest favorite

Home in Chestertown

Waterfront house with private dock & kayaks!

25 min drive

May 13 – 18

$225 per night

5.0 out of 5 average rating, 37 reviews

Guest favorite

Cottage in Kennedyville

Family-Friendly Cottage, Walk to the Beach!

20 min drive

Apr 20 – 25

$204 per night

4.96 out of 5 average rating, 25 reviews

Home in Worton

Holly Point Guest Cottage

23 min drive

Apr 20 – 25

$250 per night

New place to stay

Guest favorite

Home in Perryville

Upper Chesapeake Getaway

6 beds

Apr 28 – May 3

$223 per night, originally $262

5.0 out of 5 average rating, 71 reviews

Guest favorite

Guest suite in Chestertown

Beautiful Waterfront Chestertown Getaway

31 min drive

Jun 24 – 29

$130 per night

4.99 out of 5 average rating, 191 reviews