Chester Rentals
From $146 per night (USD)VRBO
❤️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 $146 per night (USD)VRBO
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 $387 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 $387 per night (USD)VRBO
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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 ...
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From $425 per night (USD)VRBO
Island Life! Kent Island Waterfront with Pool-Bring your boat!
- 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 $425 per night (USD)VRBO
From $356 per night (USD)Expedia
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 $356 per night (USD)Expedia
From $1166 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 $1166 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
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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. ...
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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 ...
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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
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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 $140 per night (USD)VRBO
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 $140 per night (USD)VRBO
From $795 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 $795 per night (USD)Expedia
From $125 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 $125 per night (USD)VRBO
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 $190 per night (USD)VRBO
Coastal Kent Narrows Home on Bay\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this newly renovated home on Kent Island! This place is located right in the heart of the action and is walki ...
From $190 per night (USD)VRBO
From $520 per night (USD)Expedia
Bayfront escape with screened porch, WFH desk, dock & views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Pier Pleasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $520 per night (USD)Expedia