Stevensville Rentals
- From $344 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 $344 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Cape Cod Bed and Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Second floor bed and bath with private entrance and deck located in Chesapeake Bay community. Includes 2 extra long twi ...
From $150 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Private beach spot
- Bedrooms:
- 3
- 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 $395 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
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VRBO
Come explore Maryland's Eastern Shore. Near Annapolis, Wash. D.C. and Baltimore
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful A frame chalet on Kent Island. Open concept, spacious bedrooms, multiple decks and fenced in back yard. A shor ...
Click For PricingVRBO
- From $128 per night (USD)
VRBO
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacu ...
From $128 per night (USD)VRBO
- From $1752 per night (USD)
VRBO
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 $1752 per night (USD)VRBO
- From $137 per night (USD)
VRBO
Apartment with Lounge Stevensville, MD
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully renovated 1 bedroom, 1.5 bath apartment with attached lounge! 1 set of bunk beds with two full size mattress ...
From $137 per night (USD)VRBO
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VRBO
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 ...
Click For PricingVRBO
- From $135 per night (USD)
Expedia
❤️Charming Coastal\/Country Home w\/3 Acres & Sauna!❤️
- Bedrooms:
- 3
- 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 $135 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, 5.5 bath wa ...
From $1200 per night (USD)VRBO
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Expedia
Bentons Pleasure- Cox Creek, Pier and Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WATERFRONT - 4 Bed, 3 Bath Private house in the town of Chester is available for the 2021 rental season and is an amazin ...
Click For PricingExpedia
- From $757 per night (USD)
VRBO
Sunsets and 4 King Bedrooms - Sunny Isle of Kent Across the Water from Annapolis
- 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, ...
From $757 per night (USD)VRBO
- From $475 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 $475 per night (USD)Expedia
- From $1099 per night (USD)
VRBO
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 10-12-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 $1099 per night (USD)VRBO
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Expedia
Kent Island - Gorgeous Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful waterfront property on 10 acres of land within a short drive to Annapolis and local Kent Island restaurants. ...
Click For PricingExpedia
- From $589 per night (USD)
VRBO
ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax on the expansive deck of this adult only Chesapeake Bay front cottage and enjoy the sunsets from it's grand great ...
From $589 per night (USD)VRBO
- From $356 per night (USD)
VRBO
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 $356 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Mount Vernon Apartment Rear
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 2
Featuring a garden and a terrace, Mount Vernon Apartment Rear provides accommodations in Baltimore with free WiFi and ga ...
Click For PricingVRBO
- From $1000 per night (USD)
VRBO
Kent Island Luxary Home W\/ Pool and walking distance from the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This exquisite residence is a haven of luxury and relaxation, boasting a private pool and four spacious bedrooms with in ...
From $1000 per night (USD)VRBO
- From $559 per night (USD)
Expedia
Waterfront home with private pier is A Shore Thing
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
This beautiful custom waterfront home on Cox Creek on the Eastern Shore in Chester, MD awaits you with its gorgeous wate ...
From $559 per night (USD)Expedia
- From $131 per night (USD)
VRBO
Cozy Waterfront Apartment Chester, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy th ...
From $131 per night (USD)VRBO
- From $269 per night (USD)
Expedia
Chester River Waterfront Cottage (Love Point Bay)
- 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 $269 per night (USD)Expedia
- From $699 per night (USD)
VRBO
Love Point Luxury Waterfront
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $699 per night (USD)VRBO
- From $1700 per night (USD)
Expedia
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Imagine waking up to a back and front yard nature surrounded by pine trees and a Olympic pool. Home with all glass door ...
From $1700 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Kent Island Waterfront Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kent Island waterfront cottage situated perfectly for stunning western sunset views across the waters of Cox & Thompson ...
From $200 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Private coastal decorated home, nestled in a serene 5-acre wooded lot, less than 5 miles from the Bay Bridge. Welcome to ...
From $375 per night (USD)Expedia
- From $3401 per night (USD)
VRBO
Exquisite 14,000 sq ft Waterfront Mansion with Pool
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Indulge in splendor at this sprawling 14,000-square-foot waterfront villa, spread out over 15 acres of Bayfront shorelin ...
From $3401 per night (USD)VRBO