Chester Rentals
From $333 per night (USD)VRBO
❤️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)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
From $191 per night (USD)VRBO
Cass-Away Luxury Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kent Narrows Rentals welcomes you aboard Cass-Away. A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a ...
From $191 per night (USD)VRBO
From $1474 per night (USD)Expedia
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)Expedia
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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 $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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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 $193 per night (USD)Expedia
Cass-N-Reel Luxury Houseboat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With one bedroom, on ...
From $193 per night (USD)Expedia
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 $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)Expedia
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)Expedia
From $458 per night (USD)VRBO
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)VRBO
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 $555 per night (USD)VRBO
Waterfront House: Hot Tub, Fire Pit, & Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Escape to a stunning Waterfront Getaway on Maryland's Eastern Shore! This charming house offers breathtaking wa ...
From $555 per night (USD)VRBO
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 $460 per night (USD)VRBO
Crab Alley | Waterfront Home + Hot Tub + Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Ch ...
From $460 per night (USD)VRBO
From $805 per night (USD)Expedia
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)Expedia
From $344 per night (USD)VRBO
Waterfront condo. Completely renovated. Walk to Kent Island's best places
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Invited to a Kent Island wedding or event -- going to a boat show or Navy football game? This waterfront condo is the pe ...
From $344 per night (USD)VRBO