Chester Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
50 rentals in Chester.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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Kent Island Time - Waterfront
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Kent Island - Gorgeous Waterfront Home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bentons Pleasure- Cox Creek, Pier and Sunsets!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 10-12-PETS ALLOWED
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Waterfront home with private pier is A Shore Thing
Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
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Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 20 miles of Chester match all your filters:
Private beach spot
Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cass-Away Luxury Houseboat
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Circa 1700 Chesapeake Colonial home on the National Register.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Rental Home
5 bedrooms
4 bathrooms
Sleeps 26
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Serene Waterfront Apartment on Kent Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serene Waterfront Apartment on Kent Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Abay Palace of Kent Narrows in a King Bed
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Grasonville Home w/ Private Pool on the Water
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chester River Waterfront Cottage (Love Point Bay)
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New! Stylish downtown home w/awesome outdoor area!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cape Cod Bed and Bath
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fish to the Left of Me, Geese to the right, Stuck in the middle w/ Goats
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relax on the Eastern Shore of Kent Narrows in a King Bed
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Waterfront property on 3/4 acres with private beach, pool, hot tub, and pier.
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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ADULT ONLY! Magnificent Waterfront Cottage on 5 Acres
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island waterfront spectacular Chesapeake Bay view
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
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Come explore Maryland's Eastern Shore. Near Annapolis, Wash. D.C. and Baltimore
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island House with Pool and Bay Views on wrap around deck
Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Great waterfront house in Grasonville
Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Astounding Chesapeake Bay Waterviews, Sunsets and 4 King Bedrooms
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Chesapeake Bay Views -pet friendly
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home
Rental Home
3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront 4 BR home with private pier and boat dock
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Love Point Waterfront
Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Bay Breeze - The Perfect Escape!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Love Point Luxury Waterfront
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private pier at Waterfront Kent Island home with Hot Tub (Open!)
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lighthouse Haven of Kent Island
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Lovely Chesapeake bay home, on the bay with beautiful sunsets
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Bay Haven - Stunning Newly Renovated Waterfront Home near Annapolis!
Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Kent Island Luxary Home W/ Pool and walking distance from the beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Serenity on the Water
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Apartment with Lounge Stevensville, MD
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cass-N-Reel Luxury Houseboat
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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KENT ISLAND - Everything The Narrows has to offer you!
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Belle Blu of Kent Narrows Grasonville, Maryland
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12
Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12
- Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Kent Island Time - Waterfront
- Some of the most popular kid friendly rentals in Chester are:
- Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!
- Kent Island Time - Waterfront