Chester Vacation Rentals
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5 mi
42 rentals in Chester.
Waterfront home with private pier and dog-friendly at A Shore Thing
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Cozy Waterfront Apartment Chester, MD
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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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Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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Kent Island - Gorgeous Waterfront Home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Room for an Island getaway
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Charming Waterfront home, Kent Island, Maryland!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront King Condo
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Sunset Bayview: sleeps 6
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The following properties within 20 miles of Chester match all your filters:
Island Life! Kent Island Waterfront with Pool-Bring your boat!
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240' Private Beachfront *Kent Island Love Point - Great for Large Groups
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Circa 1700 Chesapeake Colonial home on the National Register.
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Serene Waterfront Apartment on Kent Island
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Cass-Away Luxury Houseboat
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
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Cass-N-Reel Luxury Houseboat
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New! Stylish downtown home w/awesome outdoor area!
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Second Floor Bed and Bath in Stevensville, MD
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Kent Island Waterfront Cottage
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Apartment with Lounge Stevensville, MD
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Grasonville Home w/ Private Pool on the Water
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Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
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Great waterfront house in Grasonville
Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Chesapeake Bay Views -pet friendly
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Chesapeake Bay Waterfront ARTectural Home
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Kent Island Luxury Waterfront
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Waterfront 4 BR home with private pier and boat dock
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Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
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Cozy Up This Winter – Exclusive Offers Await
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Sprawling Waterfront Home with views, Dock and In-Home Theatre
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
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Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
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Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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River Front, Private Single Family Home
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Kent Island Waterfront | Pub | Outdoor Dining | Stunning View
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining.
Rental Home
24 bedrooms
24 bathrooms
Sleeps 50
Match: Sleeps
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Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
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Caribbean HEATED POOL Home near Matapeake Beach!
Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-42 of 42
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Waterfront home with private pier and dog-friendly at A Shore Thing
- Cozy Waterfront Apartment Chester, MD
- Renovated Rancher on Kent Island near Chesapeake Bay Bridge
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Waterfront home with private pier and dog-friendly at A Shore Thing
- Cozy Waterfront Apartment Chester, MD
- Renovated Rancher on Kent Island near Chesapeake Bay Bridge
- Some of the most popular kid friendly rentals in Chester are:
- Waterfront home with private pier and dog-friendly at A Shore Thing
- Cozy Waterfront Apartment Chester, MD
- Renovated Rancher on Kent Island near Chesapeake Bay Bridge