Somerset Area Rentals
- 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)VRBO
- 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
- 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)VRBO
- 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)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- 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)Expedia
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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
- 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
- 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)VRBO
- Click For Pricing
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 PricingVRBO
- Click For Pricing
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 PricingVRBO
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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
- Click For Pricing
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 PricingVRBO
- 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)VRBO
- 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)VRBO
- 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)VRBO
- 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
- 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
- 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
- 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
- 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
- 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)VRBO
- 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)VRBO
- 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
- 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)VRBO
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Click For Pricing
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 PricingVRBO
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Click For Pricing
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 ...
Click For PricingExpedia
- 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