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Vacation Rentals
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Maryland
>
Chesapeake Bay
7
BR /
6
BA /
1
HF BA /
Sleeps
26
Featured
6
BR /
6
HF BA /
Sleeps
23
Featured
8
BR /
6
BA /
Sleeps
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Featured
5
BR /
4
BA /
Sleeps
10
From $1,118/nt
Featured
3
BR /
2
BA /
Sleeps
6
From $502/nt
Featured
Chesapeake Bay Beach Cottage Rentals
(21)
sort by
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Average Rating
Availability Last Updated
Accepts Online Payments
Bedrooms: Least to Most
Bedrooms: Most to Least
Price: High to Low
Price: Low to High
Number of Reviews
Special Offers First
Darling in town cottage with private sandy beach and dock
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$398 - $472
per night
Darling in town cottage with private sandy beach and dock
2 - 7 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Oxford Cottage
#327383vb
(31)
Compare
Sea Glass Cottage on the Bay - St Michaels MD Area
3 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 6
$300 - $400
per night
Sea Glass Cottage on the Bay - St Michaels MD Area
2 night Minimum Stay
3
BR,
1
BA,
1
HF BA,
Sleeps
6
Chesapeake Bay
>
St. Michaels Cottage
#3014081
(4)
Compare
Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.
2 Bedrooms,
1
Bathroom
, Sleeps 5
Vintage Waterfront Cottage with Fishing Pier on the Chesapeake Bay.
2
BR,
1
BA,
Sleeps
5
Chesapeake Bay
>
Deal Island Cottage
#385730
(11)
Compare
Renovated cottage with Chesapeake Bay sandy beach direct access
1 Bedrooms,
1
Bathroom
, Sleeps 3
$90 - $150
per night
Renovated cottage with Chesapeake Bay sandy beach direct access
Book it Now!
2 night Minimum Stay
1
BR,
1
BA,
Sleeps
3
Chesapeake Bay
>
Point Lookout Cottage
#908053
(10)
Compare
Harbor Cottage at the Chesapeake Bay Vacation Rental
2 Bedrooms,
2
Bathrooms
, Sleeps 6
$185 - $260
per night
Harbor Cottage at the Chesapeake Bay Vacation Rental
3 night Minimum Stay
2
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
St. Leonard Cottage
#122453
(17)
Compare
St. Michael's premier in town summer vacation cottage!
2 Bedrooms,
2
Bathrooms
, Sleeps 4
St. Michael's premier in town summer vacation cottage!
2
BR,
2
BA,
Sleeps
4
Chesapeake Bay
>
St. Michaels Cottage
#287681
(26)
Compare
HERON'S REST GUEST COTTAGE - Your Paradise on the Bay!!
1 Bedrooms,
1
Bathroom
, Sleeps 4
$433
per night
HERON'S REST GUEST COTTAGE - Your Paradise on the Bay!!
2 night Minimum Stay
1
BR,
1
BA,
Sleeps
4
Chesapeake Bay
>
North Beach Cottage
#285640
(14)
Compare
Waterfront Chesapeake Bay Retreat.
3 Bedrooms,
1
Bathroom
, Sleeps 6
Waterfront Chesapeake Bay Retreat.
3
BR,
1
BA,
Sleeps
6
Chesapeake Bay
>
Tyaskin Cottage
#371260
(11)
Compare
Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C
3 Bedrooms,
1
Bathroom
, Sleeps 6
Chesapeake Bay fossil hunting from your own front yard! 50 min. D.C
3
BR,
1
BA,
Sleeps
6
Chesapeake Bay
>
St. Leonard Cottage
#138139
(4)
Compare
Ber Na Mara: Chesapeake Beach House with Panoramic Bay Views.
3 Bedrooms, Sleeps 8
$200 - $325
per night
Ber Na Mara: Chesapeake Beach House with Panoramic Bay Views.
Book it Now!
2 - 7 night Minimum Stay
3
BR,
Sleeps
8
Chesapeake Bay
>
Point Lookout Cottage
#437322vb
(7)
Compare
Waterfront Carriage House - Estate Setting - Couple's Delight
1 Bedrooms, Sleeps 2
$125 - $225
per night
Waterfront Carriage House - Estate Setting - Couple's Delight
2 night Minimum Stay
1
BR,
Sleeps
2
Chesapeake Bay
>
Cambridge Cottage
#61400vb
(16)
Compare
Classic Chesapeake Bay Cottage: Gorgeous views + beach
1 Bedrooms,
1
Bathroom
, Sleeps 3
$110 - $120
per night
Classic Chesapeake Bay Cottage: Gorgeous views + beach
Book it Now!
2 night Minimum Stay
1
BR,
1
BA,
Sleeps
3
Chesapeake Bay
>
Point Lookout Cottage
#470232vb
Compare
Cove Point Lighthouse - Both sides of the Keeper's Cottage Duplex
6 Bedrooms,
4
Bathrooms
,
2
Half Baths
, Sleeps 16
$350 - $575
per night
Cove Point Lighthouse - Both sides of the Keeper's Cottage Duplex
3 night Minimum Stay
6
BR,
4
BA,
2
HF BA,
Sleeps
16
Chesapeake Bay
>
Solomons Island Cottage
#436958vb
2 Reviews
Compare
Cove Point Lighthouse - One side of the Keeper's Cottage Duplex
3 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$184 - $400
per night
Cove Point Lighthouse - One side of the Keeper's Cottage Duplex
3 night Minimum Stay
3
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
Solomons Island Cottage
#469385vb
Compare
Cottage and or House on estate in Cambridge, MD
1 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 4
Cottage and or House on estate in Cambridge, MD
1
BR,
1
BA,
1
HF BA,
Sleeps
4
Chesapeake Bay
>
Cambridge Cottage
#429271vb
(7)
Compare
Skipjack Cottage - on the Chesapeake Bay...Come Relax
2 Bedrooms, Sleeps 6
$175
per night
Skipjack Cottage - on the Chesapeake Bay...Come Relax
2 night Minimum Stay
2
BR,
Sleeps
6
Chesapeake Bay
>
North Beach Cottage
#368160vb
(3)
Compare
Beachfront cottages
2 Bedrooms,
1
Bathroom
, Sleeps 8
Beachfront cottages
2
BR,
1
BA,
Sleeps
8
Chesapeake Bay
>
Betterton Cottage
#470915vb
Compare
Vintage Beach Cottage
2 Bedrooms,
1
Bathroom
, Sleeps 6
$300
per night
Vintage Beach Cottage
2 night Minimum Stay
2
BR,
1
BA,
Sleeps
6
Chesapeake Bay
>
Point Lookout Cottage
#347568vb
(3)
Compare
Cozy Waterfront Cottage-
3 Bedrooms, Sleeps 8
Cozy Waterfront Cottage-
3
BR,
Sleeps
8
Chesapeake Bay
>
Tyaskin Cottage
#253476vb
2 Reviews
Compare
Chesapeake Bay Md, Cottage for Yearly Rental. 1hr from D.C.
1 Bedrooms,
1
Bathroom
, Sleeps 5
Chesapeake Bay Md, Cottage for Yearly Rental. 1hr from D.C.
1
BR,
1
BA,
Sleeps
5
Chesapeake Bay
>
Chesapeake Beach Cottage
#363584vb
1 Review
Compare
Vacation Home Close to Dc. Chesapeake Bay View and Walk to the
3 Bedrooms, Sleeps 6
Vacation Home Close to Dc. Chesapeake Bay View and Walk to the
3
BR,
Sleeps
6
Chesapeake Bay
>
St. Leonard Cottage
#391580vb
1 Review
Compare
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Chesapeake Bay
Betterton (1)
Cambridge (2)
Chesapeake Beach (1)
Deal Island (1)
North Beach (2)
Oxford (1)
Point Lookout (4)
Solomons Island (2)
St. Leonard (3)
St. Michaels (2)
Tyaskin (2)