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Chester Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
42 rentals in Chester.
Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Chester
Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Chester
Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Chester

Waterfront home with private pier and dog-friendly at A Shore Thing

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Waterfront Apartment Chester, MD, holiday rental in Chester
Cozy Waterfront Apartment Chester, MD, holiday rental in Chester
Cozy Waterfront Apartment Chester, MD, holiday rental in Chester

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, holiday rental in Chester
Renovated Rancher on Kent Island near Chesapeake Bay Bridge, holiday rental in Chester
Renovated Rancher on Kent Island near Chesapeake Bay Bridge, holiday rental in Chester

Renovated Rancher on Kent Island near Chesapeake Bay Bridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Chester
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Chester
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

Holiday Rental House
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!, holiday rental in Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, holiday rental in Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, holiday rental in Chester

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island - Gorgeous Waterfront Home, holiday rental in Chester
Kent Island - Gorgeous Waterfront Home, holiday rental in Chester
Kent Island - Gorgeous Waterfront Home, holiday rental in Chester

Kent Island - Gorgeous Waterfront Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront home, Kent Island, Maryland!, holiday rental in Chester
Charming Waterfront home, Kent Island, Maryland!, holiday rental in Chester
Charming Waterfront home, Kent Island, Maryland!, holiday rental in Chester

Charming Waterfront home, Kent Island, Maryland!

Holiday Rental House
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 in Chester
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD, holiday rental in Chester
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD, holiday rental in Chester

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront King Condo, holiday rental in Chester
Waterfront King Condo, holiday rental in Chester
Waterfront King Condo, holiday rental in Chester

Waterfront King Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Sunset Bayview: sleeps 6, holiday rental in Chester
Waterfront Sunset Bayview: sleeps 6, holiday rental in Chester
Waterfront Sunset Bayview: sleeps 6, holiday rental in Chester

Waterfront Sunset Bayview: sleeps 6

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Room for an Island getaway, holiday rental in Chester
Room for an Island getaway, holiday rental in Chester
Room for an Island getaway, holiday rental in Chester

Room for an Island getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: 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!, holiday rental in Chester
Island Life!  Kent Island Waterfront with Pool-Bring your boat!, holiday rental in Chester
Island Life!  Kent Island Waterfront with Pool-Bring your boat!, holiday rental in Chester

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Chester
240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Chester
240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Chester

240' Private Beachfront *Kent Island Love Point - Great for Large Groups

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 26
Match: Sleeps
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Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Chester
Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Chester
Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Chester

Circa 1700 Chesapeake Colonial home on the National Register.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Waterfront Apartment on Kent Island, holiday rental in Chester
Serene Waterfront Apartment on Kent Island, holiday rental in Chester
Serene Waterfront Apartment on Kent Island, holiday rental in Chester

Serene Waterfront Apartment on Kent Island

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cass-Away Luxury Houseboat, holiday rental in Chester
Cass-Away Luxury Houseboat, holiday rental in Chester
Cass-Away Luxury Houseboat, holiday rental in Chester

Cass-Away Luxury Houseboat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Chester
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Chester
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Chester

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Chester

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Cass-N-Reel Luxury Houseboat, holiday rental in Chester
Cass-N-Reel Luxury Houseboat, holiday rental in Chester
Cass-N-Reel Luxury Houseboat, holiday rental in Chester

Cass-N-Reel Luxury Houseboat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New! Stylish downtown home w/awesome outdoor area!, holiday rental in Chester
New! Stylish downtown home w/awesome outdoor area!, holiday rental in Chester
New! Stylish downtown home w/awesome outdoor area!, holiday rental in Chester

New! Stylish downtown home w/awesome outdoor area!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Second Floor Bed and Bath in Stevensville, MD, holiday rental in Chester
Second Floor Bed and Bath in Stevensville, MD, holiday rental in Chester
Second Floor Bed and Bath in Stevensville, MD, holiday rental in Chester

Second Floor Bed and Bath in Stevensville, MD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Island Waterfront Cottage, holiday rental in Chester
Kent Island Waterfront Cottage, holiday rental in Chester
Kent Island Waterfront Cottage, holiday rental in Chester

Kent Island Waterfront Cottage

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Apartment with Lounge Stevensville, MD, holiday rental in Chester
Apartment with Lounge Stevensville, MD, holiday rental in Chester
Apartment with Lounge Stevensville, MD, holiday rental in Chester

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, holiday rental in Chester
Grasonville Home w/ Private Pool on the Water, holiday rental in Chester
Grasonville Home w/ Private Pool on the Water, holiday rental in Chester

Grasonville Home w/ Private Pool on the Water

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Chester
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Chester
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Chester

Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Great waterfront house in Grasonville, holiday rental in Chester
Great waterfront house in Grasonville, holiday rental in Chester
Great waterfront house in Grasonville, holiday rental in Chester

Great waterfront house in Grasonville

Holiday Rental House
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, holiday rental in Chester
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues, holiday rental in Chester
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues, holiday rental in Chester

4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Chester
Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Chester
Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Chester

Beautiful Chesapeake Bay Views -pet friendly

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, holiday rental in Chester
Chesapeake Bay Waterfront ARTectural Home, holiday rental in Chester
Chesapeake Bay Waterfront ARTectural Home, holiday rental in Chester

Chesapeake Bay Waterfront ARTectural Home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Kent Island Luxury Waterfront, holiday rental in Chester
Kent Island Luxury Waterfront, holiday rental in Chester
Kent Island Luxury Waterfront, holiday rental in Chester

Kent Island Luxury Waterfront

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront 4 BR home with private pier and boat dock, holiday rental in Chester
Waterfront 4 BR home with private pier and boat dock, holiday rental in Chester
Waterfront 4 BR home with private pier and boat dock, holiday rental in Chester

Waterfront 4 BR home with private pier and boat dock

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Chester

Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Island Life 2!  2024 remodeled home on Private Waterfront Kent Island Estate, holiday rental in Chester
Island Life 2!  2024 remodeled home on Private Waterfront Kent Island Estate, holiday rental in Chester
Island Life 2!  2024 remodeled home on Private Waterfront Kent Island Estate, holiday rental in Chester

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Chester
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Chester
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Chester

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Holiday Rental House
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 in Chester
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck., holiday rental in Chester
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck., holiday rental in Chester

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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River Front, Private Single Family Home, holiday rental in Chester
River Front, Private Single Family Home, holiday rental in Chester
River Front, Private Single Family Home, holiday rental in Chester

River Front, Private Single Family Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Waterfront | Pub | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Pub | Outdoor Dining | Stunning View, holiday rental in Chester
Kent Island Waterfront | Pub | Outdoor Dining | Stunning View, holiday rental in Chester

Kent Island Waterfront | Pub | Outdoor Dining | Stunning View

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining., holiday rental in Chester
Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining., holiday rental in Chester
Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining., holiday rental in Chester

Luxurious 24-Bedroom Mansion Retreat complete with private pool & public dining.

Holiday Rental House
24 bedrooms
24 bathrooms
Sleeps 50
Match: Sleeps
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Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Chester
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Chester
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Chester

Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Chester
Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Chester
Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Chester

Caribbean HEATED POOL Home near Matapeake Beach!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Up This Winter – Exclusive Offers Await, holiday rental in Chester
Cozy Up This Winter – Exclusive Offers Await, holiday rental in Chester
Cozy Up This Winter – Exclusive Offers Await, holiday rental in Chester

Cozy Up This Winter – Exclusive Offers Await

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sprawling Waterfront Home with views, Dock and In-Home Theatre, holiday rental in Chester
Sprawling Waterfront Home with views, Dock and In-Home Theatre, holiday rental in Chester
Sprawling Waterfront Home with views, Dock and In-Home Theatre, holiday rental in Chester

Sprawling Waterfront Home with views, Dock and In-Home Theatre

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-42 of 42
Frequently Asked Questions about Chester