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Chesapeake Bay
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534,685
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Chesapeake Beach (1)
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Kent Island (1)
North East (1)
Oxford (1)
Point Lookout (1)
Port Republic (1)
St. Leonard (2)
St. Michaels (3)
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Vacation Rentals
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Maryland
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Chesapeake Bay
6
BR /
6
BA /
Sleeps
14
From $5,425/wk
Featured
2
BR /
1
BA /
Sleeps
6
From $75/nt
Featured
6
BR /
6
HF BA /
Sleeps
23
Featured
5
BR /
4
BA /
1
HF BA /
Sleeps
13
From $742/nt
Featured
4
BR /
3
BA /
1
HF BA /
Sleeps
10
From $742/nt
Featured
Chesapeake Bay Wheelchair Accessible
(26)
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Bedrooms: Most to Least
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Special Offers First
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
4 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$400 - $700
per night
Historic Waterfront Home in St. Michaels, w/Wi-Fi, Dock & Pet Friendly
2 - 3 night Minimum Stay
4
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels House
#123352
(17)
Compare
Magical Bayfront Home
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$350 - $425
per night
Magical Bayfront Home
2 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
Port Republic House
#212770
(13)
Compare
Fishing Cove Private Waterfront Retreat with Pool and Pier
8 Bedrooms,
6
Bathrooms
, Sleeps 22
Fishing Cove Private Waterfront Retreat with Pool and Pier
8
BR,
6
BA,
Sleeps
22
Chesapeake Bay
>
Cambridge House
#178586
(17)
Compare
New,Quiet, Fun, Beachy, Colorful,Comfortable, Views,Economical,accessible apt
2 Bedrooms,
1
Bathroom
, Sleeps 6
$150
per night
New,Quiet, Fun, Beachy, Colorful,Comfortable, Views,Economical,accessible apt
2 - 7 night Minimum Stay
2
BR,
1
BA,
Sleeps
6
Chesapeake Bay
>
St. Leonard Apartment
#248524
(6)
Compare
Luxury Waterfront in Cambridge with Pool, Hot Tub, Dock!
3 Bedrooms, Sleeps 8
$379 - $459
per night
Luxury Waterfront in Cambridge with Pool, Hot Tub, Dock!
3 night Minimum Stay
3
BR,
Sleeps
8
Chesapeake Bay
>
Cambridge Cottage
#277043
(11)
Compare
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
7 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 18
$600
per night
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
3 - 7 night Minimum Stay
7
BR,
3
BA,
1
HF BA,
Sleeps
18
Chesapeake Bay
>
Cambridge House
#3477457
Compare
Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing
4 Bedrooms,
3
Bathrooms
, Sleeps 10
$300 - $450
per night
Osprey's Nest, Spacious, Peaceful, Bay Views, Sunrises, Relaxing
2 - 7 night Minimum Stay
4
BR,
3
BA,
Sleeps
10
Chesapeake Bay
>
St. Leonard House
#248526
(21)
Compare
Waterfront luxury, natural beauty, peace and tranquility
3 Bedrooms,
2
Bathrooms
, Sleeps 6
$1,300
per week
Waterfront luxury, natural beauty, peace and tranquility
3 night Minimum Stay
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Crisfield Condo
#368829
1 Review
Compare
Lighthouse Replica Home Right on the Water plus two additional waterfront homes
4 Bedrooms,
4
Bathrooms
, Sleeps 50
$450
per night
Lighthouse Replica Home Right on the Water plus two additional waterfront homes
2 night Minimum Stay
4
BR,
4
BA,
Sleeps
50
Chesapeake Bay
>
North East House
#154370
2 Reviews
Compare
Luxury Waterfront Condo With Private Boat Slip In Crisfield Maryland
3 Bedrooms,
2
Bathrooms
, Sleeps 6
Luxury Waterfront Condo With Private Boat Slip In Crisfield Maryland
3
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Crisfield Condo
#236795
1 Review
Compare
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 8
$5,502
per week
Magnificent Vacation Rental home - 'Compass Rose' with pool and dock
7 night Minimum Stay
5
BR,
2
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
St. Michaels Estate
#234152
Compare
Breathtaking 5th Floor Waterfront Condo with Boat Slip in Crisfield
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Breathtaking 5th Floor Waterfront Condo with Boat Slip in Crisfield
3
BR,
2
BA,
Sleeps
8
Chesapeake Bay
>
Crisfield Condo
#80820vb
(3)
Compare
Luxury Waterfront Condo on Chesapeake Hyatt Property
2 Bedrooms,
2
Bathrooms
, Sleeps 6
Luxury Waterfront Condo on Chesapeake Hyatt Property
2
BR,
2
BA,
Sleeps
6
Chesapeake Bay
>
Cambridge Condo
#987799
(9)
Compare
Eastern Shore Waterfront Estate, Private Beach, Deep Water
8 Bedrooms,
6
Bathrooms
,
1
Half Bath
, Sleeps 15
Eastern Shore Waterfront Estate, Private Beach, Deep Water
8
BR,
6
BA,
1
HF BA,
Sleeps
15
Chesapeake Bay
>
Oxford Estate
#211778
Compare
What a Baycation! Walk to Kentmorr Restaurant, Marina,Beach & Tiki Bar
3 Bedrooms,
3
Bathrooms
, Sleeps 12
What a Baycation! Walk to Kentmorr Restaurant, Marina,Beach & Tiki Bar
3
BR,
3
BA,
Sleeps
12
Chesapeake Bay
>
Kent Island House
#351587vb
(15)
Compare
Beautiful Waterfront Crisfield, Md Condo
3 Bedrooms, Sleeps 6
Beautiful Waterfront Crisfield, Md Condo
3
BR,
Sleeps
6
Chesapeake Bay
>
Crisfield Condo
#92250vb
(37)
Compare
Creekside Hideaway
2 Bedrooms,
1
Bathroom
,
1
Half Bath
, Sleeps 8
$200 - $350
per night
Creekside Hideaway
2 night Minimum Stay
2
BR,
1
BA,
1
HF BA,
Sleeps
8
Chesapeake Bay
>
Point Lookout House
#465337vb
Compare
Waterfront Country Estate Featured in Chesapeake Life Magazine
10 Bedrooms,
1
Half Bath
, Sleeps 26
$5,005 - $7,000
per week
Waterfront Country Estate Featured in Chesapeake Life Magazine
7 night Minimum Stay
10
BR,
1
HF BA,
Sleeps
26
Chesapeake Bay
>
Cambridge Estate
#13516vb
(3)
Compare
Available for the race weekend! 21 Farm, Dock & Boat Ramp, 3-Day Wknds Avail.
4 Bedrooms,
3
Bathrooms
, Sleeps 12
Available for the race weekend! 21 Farm, Dock & Boat Ramp, 3-Day Wknds Avail.
4
BR,
3
BA,
Sleeps
12
Chesapeake Bay
>
Cambridge House
#406715vb
(5)
Compare
Heron Cove *Private Family Retreat* Summer $4000/wk
7 Bedrooms,
5
Bathrooms
, Sleeps 20
Heron Cove *Private Family Retreat* Summer $4000/wk
7
BR,
5
BA,
Sleeps
20
Chesapeake Bay
>
St. Michaels House
#89088vb
(6)
Compare
Sunset Bay, Sleeps 16, Breathtaking Sunsets, Enjoy the Sho
5 Bedrooms, Sleeps 16
Sunset Bay, Sleeps 16, Breathtaking Sunsets, Enjoy the Sho
5
BR,
Sleeps
16
Chesapeake Bay
>
Cambridge House
#398711vb
Compare
Brittland Manor
11 Bedrooms,
8
Bathrooms
,
1
Half Bath
, Sleeps 26
Brittland Manor
11
BR,
8
BA,
1
HF BA,
Sleeps
26
Chesapeake Bay
>
Chestertown Estate
#223074vb
Compare
The Farm House in Dames Quarter, Maryland
6 Bedrooms, Sleeps 12
The Farm House in Dames Quarter, Maryland
6
BR,
Sleeps
12
Chesapeake Bay
>
Deal Island Farmhouse
#215694vb
(17)
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
Cozy 3 Bdroom Home with Private Beach Access to Choptank River
3 Bedrooms, Sleeps 6
Cozy 3 Bdroom Home with Private Beach Access to Choptank River
3
BR,
Sleeps
6
Chesapeake Bay
>
Cambridge House
#384040vb
Compare
Beautiful Waterfront Condo with Boat Dockage on Eastern Shore
3 Bedrooms, Sleeps 8
Beautiful Waterfront Condo with Boat Dockage on Eastern Shore
3
BR,
Sleeps
8
Chesapeake Bay
>
Crisfield Condo
#302800vb
1 Review
Compare
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Chesapeake Bay
Cambridge (8)
Chesapeake Beach (1)
Chestertown (1)
Crisfield (5)
Deal Island (1)
Kent Island (1)
North East (1)
Oxford (1)
Point Lookout (1)
Port Republic (1)
St. Leonard (2)
St. Michaels (3)