Stevensville Rentals
From $168 per night (USD)VRBO
Second Floor Bed and Bath in Stevensville, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Second floor bed and bath with private entrance, dedicated HVAC, and balcony overlooking the backyard, located in Chesap ...
From $168 per night (USD)VRBO
From $333 per night (USD)Expedia
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home with 3 acres of outdoor living! Perfect for Families ...
From $333 per night (USD)Expedia
From $1920 per night (USD)VRBO
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, ...
From $1920 per night (USD)VRBO
From $156 per night (USD)VRBO
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacu ...
From $156 per night (USD)VRBO
From $325 per night (USD)VRBO
New! Stylish downtown home w/awesome outdoor area!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tastefully updated 3 bedroom home with everything you need to enjoy Kent Island! All new furniture and bedding! Home is ...
From $325 per night (USD)VRBO
From $444 per night (USD)Expedia
Island Life! Kent Island Waterfront with Pool-Bring your boat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up t ...
From $444 per night (USD)Expedia
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4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Are you looking for a holiday by the bay, a small reunion, a family vacation, a getaway, a golf outing, a fishing trip, ...
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From $550 per night (USD)Expedia
Circa 1700 Chesapeake Colonial home on the National Register.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Over 3000sf. Fully stocked, (just remodeled) kitchen, study, formal dining room, large living room, full bath, all down ...
From $550 per night (USD)Expedia
From $1474 per night (USD)VRBO
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 8-10-PETS ALLOWED.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Weekend or weekly getaway in this 3000 SF house located in Kent Island MD, surrounded by the beautiful waters of the Che ...
From $1474 per night (USD)VRBO
From $221 per night (USD)VRBO
Serene Waterfront Apartment on Kent Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located across the bay from Annapolis (just 1.5 miles from the bridge), we offer a convenient, quiet, and beautiful alte ...
From $221 per night (USD)VRBO
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Kent Island - Gorgeous Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful waterfront property on 10 acres of land within a short drive to Annapolis and local Kent Island restaurants. ...
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From $370 per night (USD)Expedia
Kent Island Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $370 per night (USD)Expedia
From $804 per night (USD)VRBO
Kent Island Luxury Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $804 per night (USD)VRBO
From $413 per night (USD)Expedia
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We always clean and disinfect the home using extra cleaning recommendations from the Centers for Disease Control and Pre ...
From $413 per night (USD)Expedia
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Kent Island waterfront spectacular Chesapeake Bay view
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We hope you will enjoy our newly renovated waterfront home as much as we do. Family friendly environment, bird watchi ...
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Renovated Rancher on Kent Island near Chesapeake Bay Bridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy yet modern rancher equipped with 3 bedrooms, 2 baths, and spacious open floor plan! Whether you’re looking to be cl ...
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From $705 per night (USD)VRBO
Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy waterfront views of Cox Creek from this stunning custom home on Maryland’s Eastern Shore. With its private pier, e ...
From $705 per night (USD)VRBO
From $84 per night (USD)Expedia
Cozy Waterfront Apartment Chester, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*We live on the property* NO SMOKING OF ANY KIND is permitted in this apartment or on the property whatsoever. The apar ...
From $84 per night (USD)Expedia
From $534 per night (USD)VRBO
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Recently upgraded heating, ventilation and air conditioning with new ductless system. This private coastal decorated ho ...
From $534 per night (USD)VRBO
From $1269 per night (USD)Expedia
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Relax and unwind at this spa-like luxury waterfront estate. Located on the Chesapeake Bay, this newly constructed vacati ...
From $1269 per night (USD)Expedia
From $707 per night (USD)VRBO
Caribbean HEATED POOL Home near Matapeake Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This exquisite Eastern Shore residence is perfect for relaxation and a quick trip to the beach or Annapolis, bo ...
From $707 per night (USD)VRBO
From $567 per night (USD)VRBO
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 ho ...
From $567 per night (USD)VRBO
From $484 per night (USD)VRBO
Welcome to The Blue Crab House Stevensville Maryland Eastern Shore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome To The Blue Crab House Full of your finest eastern shore charm in Stevensville Maryland this spacious 3 bedroo ...
From $484 per night (USD)VRBO
From $199 per night (USD)VRBO
Room for an Island getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy easy access to everything from this perfectly located room with water views off of Rt. 50 between the Chesapeake B ...
From $199 per night (USD)VRBO
From $318 per night (USD)VRBO
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready to relax in this brilliant 3-bedroom coastal-country home in Stevensville. Remodeled and refurnished complete ...
From $318 per night (USD)VRBO
From $458 per night (USD)Expedia
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Kent Island from this 3-bedroom house. This fantastic property offers a king bed, a queen bed, an ...
From $458 per night (USD)Expedia
From $613 per night (USD)VRBO
Pier Pleasure Retreat- Waterfront & Private Pier
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Pier Pleasure Retreat: Your Waterfront Oasis Welcome to Pier Pleasure Retreat, a newly renovated 4-bedroom, 4-bathroom ...
From $613 per night (USD)VRBO
From $169 per night (USD)Expedia
Chesapeake Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
VERY CLOSE to Island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen ...
From $169 per night (USD)Expedia
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Beautiful Kent Island Getaway with Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your family entertaining. You will lov ...
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From $634 per night (USD)Expedia
Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Charming Kent Island Retreat – 4 BR • 2.5 BA • Pool Table • Near the Water ""Brand New Construction"" Escape to the East ...
From $634 per night (USD)Expedia
From $805 per night (USD)VRBO
Kent Island Maryland Getaway
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Wade a Minute Chester Escape to a charming waterfront retreat located in Chester, MD, this impressive 5-bedroom, 3.5 ba ...
From $805 per night (USD)VRBO