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Results: 59 Rentals

  • SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
    From $175 per night (USD)

    VRBO

    SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    ***CONTACT OWNER FOR HOLIDAY RATES!!! The Harbour Light Condominiums are the Waterfront Jewel of Crisfield. This unit ...

    From $175 per night (USD)

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    Details
  • IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
    From $175 per night (USD)

    Expedia

    IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Unwind and relax after a busy life in the city. Get comfortable and enjoy plenty of extra room at this spacious place. ...

    From $175 per night (USD)

    Expedia

    Details
  • Cottage near the Bay
    From $90 per night (USD)

    VRBO

    Cottage near the Bay

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    9

    Come to our cozy cottage that is a 5 minute drive from the bay. We have a little yard and a grill for making fish. Crisf ...

    From $90 per night (USD)

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    Details
  • Kingsbay Mansion Bayhouse
    From $810 per night (USD)

    VRBO

    Kingsbay Mansion Bayhouse

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Kingsbay Bayhouse is an exclusive private waterfront house separated by a 70 foot grand solarium hallway off Kingsbay Ma ...

    From $810 per night (USD)

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    Details
  • Relaxing 4 bed 3 bath Waterfront Retreat in Princess Anne, MD.
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    Relaxing 4 bed 3 bath Waterfront Retreat in Princess Anne, MD.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    4 Bedroom, 3 Bathroom home on Maryland’s Eastern Shore with beautiful views of St. Peter’s Creek/Manokin River. Spectacu ...

    Click For Pricing

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    Details
  • Historic home on Smith Island w\/ dock!
    From $230 per night (USD)

    Expedia

    Historic home on Smith Island w\/ dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Pearl on Smith Island is a completely restored Eastern Shore farmhouse with the classic pitched roof. Built in 1900 ...

    From $230 per night (USD)

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    Details
  • Blue Heron Cottage On Smith's Island
    From $128 per night (USD)

    VRBO

    Blue Heron Cottage On Smith's Island

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Smith Island's newest jewel, newly constructed waterfront cottage that sleeps 6 comfortably. Relax on the front porch a ...

    From $128 per night (USD)

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    Details
  • Direct Waterfront Chesapeake Bay Condo
    From $300 per night (USD)

    Expedia

    Direct Waterfront Chesapeake Bay Condo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    A boating and fishing paradise on the Chesapeake Bay at Harbour Light in Crisfield on the Eastern Shore of Maryland. C ...

    From $300 per night (USD)

    Expedia

    Details
  • Breathtaking Top Floor Waterfront Condo with Boat Slip in Crisfield
    From $285 per night (USD)

    VRBO

    Breathtaking Top Floor Waterfront Condo with Boat Slip in Crisfield

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Relax with that special someone in this Exquisitely-Decorated 5th floor 3 Bedroom 2 Bath water front. Melt with a glass ...

    From $285 per night (USD)

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    Details
  • Home of the Terrapin King
    From $310 per night (USD)

    Expedia

    Home of the Terrapin King

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    HISTORIC, WATERFRONT HOME ON MARYLAND’S EASTERN SHORE (CRISFIELD, MD) – SECLUDED/QUAINT/PEACEFUL The LaVallette House ...

    From $310 per night (USD)

    Expedia

    Details
  • Beautiful Waterfront Condo w\/ Community Pool!
    From $244 per night (USD)

    VRBO

    Beautiful Waterfront Condo w\/ Community Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    What better way to start your day than by sitting peacefully on a private balcony with unbeatable bay views while sippin ...

    From $244 per night (USD)

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    Details
  • Kingsbay Dockside Waterfront House
    From $743 per night (USD)

    VRBO

    Kingsbay Dockside Waterfront House

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Kingsbay Dockside is located at 5757 Dockside Lane just across the water from Kingsbay Mansion. This unique offering is ...

    From $743 per night (USD)

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    Details
  • The Best View in the Blue Crab Capital of the World!
    From $190 per night (USD)

    VRBO

    The Best View in the Blue Crab Capital of the World!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Make yourself at home away from home at this 2 bed, 2 bath condo that overlooks Somer's Cove in Crisfield, MD. Each morn ...

    From $190 per night (USD)

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    Details
  • Simply the best...Beautiful condo overlooking the Chesapeake bay.
    From $278 per night (USD)

    Expedia

    Simply the best...Beautiful condo overlooking the Chesapeake bay.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 bedroom 2 bath condo with a private boat slip so bring your boat, jet skis and kayaks. One hour drive to Chincoteague ...

    From $278 per night (USD)

    Expedia

    Details
  • Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
    From $169 per night (USD)

    VRBO

    Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Come to Smith Island by your own boat or the several ferries that run daily. Experience the relaxation of the true islan ...

    From $169 per night (USD)

    VRBO

    Details
  • Cozy Waterfront Cottage\n\n
    From $170 per night (USD)

    VRBO

    Cozy Waterfront Cottage\n\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Waterfront cottage located on Tangier Sound. Sleeps 6; 1 Bedroom with queen size bed, 1 Bath with walk in shower, Kitch ...

    From $170 per night (USD)

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    Details
  • Bed & Breakfast
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    VRBO

    Bed & Breakfast

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Luxury en suite bathroom with clawfoot tub and large separate shower. This room is beautifully decorated, so cosy you ...

    Click For Pricing

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    Details
  • Eastern Shore Waterfront Cottage on Historical Estate
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    VRBO

    Eastern Shore Waterfront Cottage on Historical Estate

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Waterfront Cottage situated on historical estate. Cottage is all updated with full kitchen, central a/c and furnishings. ...

    Click For Pricing

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    Details
  • Spectacular Sunsets- Waterfront Home on Smith Island
    From $145 per night (USD)

    VRBO

    Spectacular Sunsets- Waterfront Home on Smith Island

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    16

    Gorgeously appointed and newly renovated large historic four bedroom, two story home, on the water in Tylerton, Smith Is ...

    From $145 per night (USD)

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    Details
  • Spectacular Sunsets- Waterfront Home On Smith Island
    From $145 per night (USD)

    VRBO

    Spectacular Sunsets- Waterfront Home On Smith Island

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    16

    Gorgeously appointed and newly renovated large historic four bedroom, two story home, on the waterfront in Tylerton, Smi ...

    From $145 per night (USD)

    VRBO

    Details
  • British owned vacation Bed & Breakfast!
    From $451 per night (USD)

    VRBO

    British owned vacation Bed & Breakfast!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Three bedrooms each with its own private full bathroom. FREE BREAKFAST INCLUDED ! Bring your favorite book to Princess ...

    From $451 per night (USD)

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    Details
  • Chesapeake Bay family retreat - crab, fish, swim, and boat.  70' Private beach
    From $1100 per night (USD)

    VRBO

    Chesapeake Bay family retreat - crab, fish, swim, and boat. 70' Private beach

    Bedrooms:
    4
    Bathrooms:
    8
    Sleeps:
    20

    Nestled on over 10,000 acres of marshland, our 250+ acre parcel is a nature lovers dream. The fully renovated historic ...

    From $1100 per night (USD)

    VRBO

    Details
  • Relax on River just south of Salisbury- Recently updated!
    From $218 per night (USD)

    VRBO

    Relax on River just south of Salisbury- Recently updated!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Due to county restrictions during COVID-19 some requests maybe denied. It is extremely helpful to tell us why you are co ...

    From $218 per night (USD)

    VRBO

    Details
  • Chesapeake Waterfront with Private Dock in Crisfield, Maryland
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    VRBO

    Chesapeake Waterfront with Private Dock in Crisfield, Maryland

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy beautiful days on the water, either at 'home' crabbing, fishing or swimming from your private 120' dock, or out on ...

    Click For Pricing

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    Details
  • Deal Island Bay Cottage
    From $164 per night (USD)

    VRBO

    Deal Island Bay Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy the Lower Eastern Shore of Maryland and the Chesapeake Bay in a relaxing and peaceful way. The Deal Island Bay Cot ...

    From $164 per night (USD)

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    Details
  • The Relax-Inn Deal Island with Kayaks and Canoe
    From $125 per night (USD)

    VRBO

    The Relax-Inn Deal Island with Kayaks and Canoe

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Spend time relaxing in the QUIET and Rural fishing community of Deal Island. This quaint cape cod offers large dining ...

    From $125 per night (USD)

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    Details
  • Paradise Awaits........
    From $429 per night (USD)

    VRBO

    Paradise Awaits........

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    13

    This gorgeous waterfront home boasts its own beautiful, private 100 ft pier and shoreline. Crab and fish right off the p ...

    From $429 per night (USD)

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    Details
  • Kingsbay Waterside Retreat House
    From $650 per night (USD)

    VRBO

    Kingsbay Waterside Retreat House

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Kingsbay Waterside Retreat House is an elegant, modern, waterfront compound and definitely one of a kind. Located on Mar ...

    From $650 per night (USD)

    VRBO

    Details
  • The Cottage at Kingsbay Mansion Executive B&B
    From $245 per night (USD)

    VRBO

    The Cottage at Kingsbay Mansion Executive B&B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Kingsbay Waterside Cottage is located at 5818 Pinewood Court, Marion, MD 21838. It is across the creek and it is not pa ...

    From $245 per night (USD)

    VRBO

    Details
  • Waterfront Marion Station Retreat w\/ Private Dock!
    From $277 per night (USD)

    Expedia

    Waterfront Marion Station Retreat w\/ Private Dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Escape to ‘Sunsets Waiting,’ a dreamy 3-bedroom, 3-bath vacation rental on the shores of Colbourn Creek. Explore nearby ...

    From $277 per night (USD)

    Expedia

    Details
  • Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
    From $250 per night (USD)

    VRBO

    Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Enjoy incredible sunsets from the privacy of the top floor balcony of the newly renovated 3 Bedroom and 2 Bathroom condo ...

    From $250 per night (USD)

    VRBO

    Details
  • Spectacular Waterfront on the Pocomoke River!
    From $175 per night (USD)

    Expedia

    Spectacular Waterfront on the Pocomoke River!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    “A good River is Nature’s life work in song….” The sound of the breeze rustling through the trees. The smell of a campf ...

    From $175 per night (USD)

    Expedia

    Details
  • Stylish Condo with a Great View
    From $264 per night (USD)

    VRBO

    Stylish Condo with a Great View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This unique place has a style of its own. Beautiful furnishings and arts throughout and comfort and peace within. Its lo ...

    From $264 per night (USD)

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    Details
  • Get away to relax on Smith Island in the Chesapeake Bay
    From $175 per night (USD)

    VRBO

    Get away to relax on Smith Island in the Chesapeake Bay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedro ...

    From $175 per night (USD)

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    Details
  • BED & BREAK
    From $149 per night (USD)

    VRBO

    BED & BREAK

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    BED & BREAKFAST This bedroom is beautifully decorated, so cosy you immediately feel at home. Our peaceful and beautifu ...

    From $149 per night (USD)

    VRBO

    Details
  • Bed & Breakfast
    From $149 per night (USD)

    VRBO

    Bed & Breakfast

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Bed & Breakfast 1 Bedroom w/ bathroom. This bedroom is beautifully decorated, so cosy you immediately feel at home. Our ...

    From $149 per night (USD)

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    Details
  • Waterfront 3 bedroom condo. Spring is coming! Enjoy local oysters!
    From $188 per night (USD)

    VRBO

    Waterfront 3 bedroom condo. Spring is coming! Enjoy local oysters!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome Spring in Crisfield! Mar. 6 - 31st Photo Contest sponsored by Chesapeake Bay Foundation Mar. 31 - Apr. 13 - Loo ...

    From $188 per night (USD)

    VRBO

    Details
  • Waterfront Condo and Boat Slip on the Beautiful Tangier Sound of Chesapeake.
    From $150 per night (USD)

    Expedia

    Waterfront Condo and Boat Slip on the Beautiful Tangier Sound of Chesapeake.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Situated in the highly-sought-after Tangier Sound Condominium, this elegant condo beautifully-fully-furnished, with 3 be ...

    From $150 per night (USD)

    Expedia

    Details
  • NEWLY REMODELED COZY APARTMENT with WATER VIEWS & AMAZING SUNSETS in CRISFIELD!!
    From $160 per night (USD)

    VRBO

    NEWLY REMODELED COZY APARTMENT with WATER VIEWS & AMAZING SUNSETS in CRISFIELD!!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Enjoy a relaxing stay at the gorgeous remodeled "HOUSE OF BLUES" apartment unit with water views! We strive to be the be ...

    From $160 per night (USD)

    VRBO

    Details
  • BEAUTIFUL REMODELED \COTTAGE BY THE BAY\ in CRISFIELD! WE STRIVE TO BE THE BEST!
    From $178 per night (USD)

    Expedia

    BEAUTIFUL REMODELED \"COTTAGE BY THE BAY\" in CRISFIELD! WE STRIVE TO BE THE BEST!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to this beautifully remodeled "COTTAGE BY THE BAY" in the charming town of Crisfield! Premier Partner over 8 yea ...

    From $178 per night (USD)

    Expedia

    Details
  • The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views
    From $150 per night (USD)

    VRBO

    The Sportman's Cottage House- Perfect for relation, fun and enjoying beautiful views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Relax with friends and family at this peaceful home where the living is easy. When you stay here, you will enjoy water v ...

    From $150 per night (USD)

    VRBO

    Details
  • Victorian Get Away
    From $275 per night (USD)

    VRBO

    Victorian Get Away

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Bring the whole family to this great place with lots of room for fun. Owners have thought of all the details for a famil ...

    From $275 per night (USD)

    VRBO

    Details
  • Crisfield Vacation Rental Condo w\/ Community Pool!
    From $325 per night (USD)

    VRBO

    Crisfield Vacation Rental Condo w\/ Community Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Memories are waiting to be made at this breezy 3-bedroom, 2-bathroom Crisfield vacation rental. This 5th-floor condo — w ...

    From $325 per night (USD)

    VRBO

    Details
  • Cozy Contemporary Home
    From $300 per night (USD)

    Expedia

    Cozy Contemporary Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nice warm unique home peaceful relaxing. Enjoy the clam bake and crab feast cruise or on the shore. Great shopping spot ...

    From $300 per night (USD)

    Expedia

    Details
  • Bizzys Bungalow, 2 bedroom with wifi and golf cart
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    VRBO

    Bizzys Bungalow, 2 bedroom with wifi and golf cart

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax with the whole family, or just for a romantic getaway at this peaceful home thats full of vintage charm. Enjoy ri ...

    Click For Pricing

    VRBO

    Details
  • SummerSets!! On the river bend…
    From $550 per night (USD)

    Expedia

    SummerSets!! On the river bend…

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    10

    Spacious, serene cabin on the Pocomoke River! Cabin sleeps 8-10 comfortably but maintains all the charm of a cozy riverf ...

    From $550 per night (USD)

    Expedia

    Details
  • Come, sit back and relax at the \Catch of the Bay\
    From $165 per night (USD)

    VRBO

    Come, sit back and relax at the \"Catch of the Bay\"

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to the completely remodeled “Catch of the Bay” cottage! You will enjoy calling this beachy yet rustic location w ...

    From $165 per night (USD)

    VRBO

    Details
  • Quaint Island Getaway
    From $222 per night (USD)

    Expedia

    Quaint Island Getaway

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Recently renovated 1960's farmhouse located in an authentic watermen's community. -Pets allowed *** with approval at ti ...

    From $222 per night (USD)

    Expedia

    Details
  • Promise Point, Bay Front home with dock 3BR 2BA surrounded by water
    From $250 per night (USD)

    VRBO

    Promise Point, Bay Front home with dock 3BR 2BA surrounded by water

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    Take it easy at this unique and tranquil getaway. Open floor plan home completely renovated in 2022. Surrounded by water ...

    From $250 per night (USD)

    VRBO

    Details
  • Cute, cozy cottage getaway
    From $82 per night (USD)

    VRBO

    Cute, cozy cottage getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Cute, cozy, and cheery...this little ranch house is on a quiet street in the quaint fishing village of Wenona, a small c ...

    From $82 per night (USD)

    VRBO

    Details
  • Welcome to the best view in Crisfield! top floor condo!
    From $258 per night (USD)

    VRBO

    Welcome to the best view in Crisfield! top floor condo!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Condo3 Beds2 Full Baths1,428 Sq. Ft.Updated 2 days ago 1 Photo Map & Location 103 Williams Street #615 - Photo 1 1/1 M ...

    From $258 per night (USD)

    VRBO

    Details
  • Chesapeake Bay Waterfront Home
    From $145 per night (USD)

    VRBO

    Chesapeake Bay Waterfront Home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Please don't send a reservation request. Please review the rental agreement under the rules and policies, then send a in ...

    From $145 per night (USD)

    VRBO

    Details
  • Rock Hall on the water
    From $228 per night (USD)

    VRBO

    Rock Hall on the water

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    *New 2023* - Refinished ground level (two doubles with en suite full bath) - Full house HVAC (AC and Heat) Built in 18 ...

    From $228 per night (USD)

    VRBO

    Details
  • Beautiful Eastern Shore River Cottage near Salisbury
    From $385 per night (USD)

    VRBO

    Beautiful Eastern Shore River Cottage near Salisbury

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Relax overlooking the beautiful Wicomico River on the Eastern Shore of Maryland. Enjoy morning coffee on the porch wat ...

    From $385 per night (USD)

    VRBO

    Details
  • Home in historic Whitehaven Village.
    From $250 per night (USD)

    VRBO

    Home in historic Whitehaven Village.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Relax with the whole family at this peaceful place to stay in the historic village of Whitehaven, Maryland. Three comf ...

    From $250 per night (USD)

    VRBO

    Details
  • Creek House - Waterfront Oasis on Holden's Creek
    From $267 per night (USD)

    Expedia

    Creek House - Waterfront Oasis on Holden's Creek

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Creek House, Privately located in an imaginative setting; nature and history are perfectly coupled with luxurious accomm ...

    From $267 per night (USD)

    Expedia

    Details
  • Pet-Friendly Quantico Home w\/ River Views!
    From $260 per night (USD)

    VRBO

    Pet-Friendly Quantico Home w\/ River Views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Treat your family to a riverfront retreat and book this 4-bedroom, 2.5-bath Quantico vacation rental! Nestled on the Wic ...

    From $260 per night (USD)

    VRBO

    Details
  • Home away from Home
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    Expedia

    Home away from Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Entire House: Conveniently located just one minute off of RT 13, this house is the perfect location for your family as y ...

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    Expedia

    Details
  • Sunnybank Getaway - Waterfront w\/Pier & Kayaks in Reedville, VA
    From $150 per night (USD)

    VRBO

    Sunnybank Getaway - Waterfront w\/Pier & Kayaks in Reedville, VA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape the city life and embrace this tranquil Northern Neck getaway today! Come enjoy the waterfront panoramic view of ...

    From $150 per night (USD)

    VRBO

    Details