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Cottages, Villas, Apartments in Chester
Holiday Rentals
USA
Maryland (MD)
Kent Island
Cottages, Villas, Apartments in Chester
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Air Conditioning (42)
Internet or Wifi (41)
Washer/Dryer (36)
Other outdoor space (32)
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Suitability
Kid friendly (38)
Pet friendly (16)
Smoking allowed (2)
Wheelchair access (0)
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Holiday Rental House (37)
Condominium/Apartment (5)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (25)
Boat Available (1)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Chesapeake Heritage & Visitor Center
Kent Island Frame Shop
Taste Buds Kitchen
Bella Rose Medical Aesthetics
Delmarva Balloon Rides
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42 rentals
in Chester.
Waterfront home with private pier and dog-friendly at A Shore Thing
20
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
Cozy Waterfront Apartment Chester, MD
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
8
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
20
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Kent Island - Gorgeous Waterfront Home
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Charming Waterfront home, Kent Island, Maryland!
Holiday Rental House
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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
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Waterfront King Condo
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Waterfront Sunset Bayview: sleeps 6
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Room for an Island getaway
1
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Sleeps
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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!
56
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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As seen on
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
169
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 26
Match:
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Circa 1700 Chesapeake Colonial home on the National Register.
25
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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As seen on
Serene Waterfront Apartment on Kent Island
43
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Cass-Away Luxury Houseboat
45
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
17
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
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As seen on
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
9
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 16
Match:
Sleeps
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Cass-N-Reel Luxury Houseboat
17
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
New! Stylish downtown home w/awesome outdoor area!
17
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Second Floor Bed and Bath in Stevensville, MD
22
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Kent Island Waterfront Cottage
7
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Apartment with Lounge Stevensville, MD
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Grasonville Home w/ Private Pool on the Water
13
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
8
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Great waterfront house in Grasonville
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
Beautiful Chesapeake Bay Views -pet friendly
2
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Chesapeake Bay Waterfront ARTectural Home
11
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Kent Island Luxury Waterfront
4
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
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As seen on
Waterfront 4 BR home with private pier and boat dock
8
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
8
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 14
Match:
Sleeps
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As seen on
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
7
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
River Front, Private Single Family Home
6
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Kent Island Waterfront | Pub | Outdoor Dining | Stunning View
Holiday Rental House
View on map
5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining.
Holiday Rental House
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24 bedrooms
24 bathrooms
Sleeps 50
Match:
Sleeps
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As seen on
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
5
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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Caribbean HEATED POOL Home near Matapeake Beach!
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Cozy Up This Winter – Exclusive Offers Await
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
1
Showing results 1-42 of 42
Frequently Asked Questions about Chester
Do any holiday rentals in Chester have a pool?
Yes, here are some popular holiday 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
See all holiday rentals with a pool in Chester on Tripadvisor
Do any holiday rentals in Chester have internet access?
Yes, here are some popular holiday 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
See all holiday rentals in Chester on Tripadvisor
What are the best pet friendly rentals in Chester?
The best pet 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
See all pet friendly holiday rentals in Chester on Tripadvisor
What are some great rentals in Chester that are kid friendly?
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
See all kid friendly holiday rentals in Chester on Tripadvisor
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