Vacation Rentals in Chester, MD
PRICE PER NIGHT
ACCOMMODATION TYPES
Bentons Pleasure- Cox Creek, Pier and Sunsets!
9.9
Excellent
·
Chester
·
4 br
·
Sleeps 10
·
Outdoor Space · Fitness Center · Deck ·
From
$868/nightProperty
House · 4 Beds · 3 baths
Amenities
Fitness Center
Air Conditioning
Fireplace
Waterfront
Oven
Dishwasher
Furnished
In Unit Laundry
Other spaces
Deck, Balcony, Kitchen
Stunning Waterfront Guest Cottage- Sunsets, Pool, Pier
10
Excellent
·
Chester
·
2 br
·
Sleeps 10
·
Pool · Private Pool · Fireplace ·
From
$395/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Pool
Private Pool
Fireplace
Waterfront
Oven
Dishwasher
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Peaceful, Waterfront Home On 3 Acres (pier + western view w/gorgeous sunsets)
9.8
Excellent
·
Chester
·
4 br
·
Sleeps 8
·
Workspace · Air Conditioning · Dishwasher ·
From
$448/nightProperty
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
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Private beach spot
9.9
Excellent
·
Stevensville
·
3 br
·
Hot Tub · Pool · Fitness Center ·
From
$418/nightProperty
House · 3 Beds · 3 baths
Amenities
Hot Tub
Pool
Fitness Center
Private Pool
Air Conditioning
Fireplace
Waterfront
Oven
Other spaces
Balcony, Kitchen
Cass-Away Luxury Houseboat
9.9
Excellent
·
Grasonville
·
2 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · Oven ·
From
$279/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Air Conditioning
Oven
Furnished
In Unit Laundry
Wifi
Roof Deck
Other spaces
Kitchen
Waterfront property on 3/4 acres with private beach, pool, hot tub, and pier.
No reviews
·
Grasonville
·
2 br
·
Sleeps 5
·
Beach · Hot Tub · Outdoor Space ·
From
$279/nightProperty
House · 2 Beds · 1 bath
Amenities
Beach
Hot Tub
Pool
Fitness Center
Private Pool
Air Conditioning
Fireplace
Waterfront
Other spaces
Kitchen
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
7.8
Very good
·
Stevensville
·
3 br
·
Sleeps 4
·
Fitness Center · Air Conditioning · Fireplace ·
From
$128/nightProperty
House · 3 Beds · 3 baths
Amenities
Fitness Center
Air Conditioning
Fireplace
Waterfront
Oven
Dishwasher
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
No reviews
·
Stevensville
·
3 br
·
Sleeps 14
·
Workspace · Air Conditioning · Oven ·
From
$58/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Garage Parking
Business Center
Other spaces
Workspace, Kitchen
Kent Island waterfront spectacular view
No reviews
·
Stevensville
·
3 br
·
Sleeps 8
·
Outdoor Space · Workspace · Air Conditioning ·
From
$650/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Oven
Furnished
In Unit Laundry
Wifi
Swimming Pool
Other spaces
Workspace, Kitchen
Love Point Luxury Waterfront
No reviews
·
District 4 Kent Island
·
4 br
·
Sleeps 10
·
Ev Charging · Deck · Air Conditioning ·
From
$999/nightProperty
House · 4 Beds · 4 baths
Amenities
Ev Charging
Air Conditioning
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Garage Parking
Other spaces
Deck, Balcony, Kitchen
Chester River Waterfront Cottage (Love Point Bay)
8
Very good
·
District 4 Kent Island
·
2 br
·
Sleeps 6
·
Deck · Workspace · Air Conditioning ·
From
$332/nightProperty
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Residents Lounge
Other spaces
Deck, Workspace, Kitchen
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LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
No reviews
·
Chester
·
4 br
·
Sleeps 10
·
Oven · Furnished · Kitchen ·
From
$1,700/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Oven
Furnished
Swimming Pool
Other spaces
Kitchen
New! Stylish downtown home w/awesome outdoor area!
10
Excellent
·
Stevensville
·
3 br
·
Sleeps 8
·
Beach · Air Conditioning · Oven ·
From
$342/nightProperty
House · 3 Beds · 2 baths
Amenities
Beach
Air Conditioning
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 10-12-PETS ALLOWED
10
Excellent
·
Chester
·
4 br
·
Sleeps 10
·
Assigned Parking · Outdoor Space · Pool ·
From
$1,241/nightProperty
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Pool
Air Conditioning
Fireplace
Oven
Dishwasher
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
Circa 1700 Chesapeake Colonial home on the National Register.
9.8
Excellent
·
District 4 Kent Island
·
4 br
·
Sleeps 8
·
Pool · Workspace · Air Conditioning ·
From
$411/nightProperty
House · 4 Beds · 3 baths
Amenities
Pool
Air Conditioning
Fireplace
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Blue Bay Haven - Stunning Newly Renovated Waterfront Home near Annapolis!
8.7
Very good
·
Stevensville
·
7 br
·
Sleeps 16
·
Pool · Private Pool · Workspace ·
From
$1,200/nightProperty
House · 7 Beds · 6 baths
Amenities
Pool
Private Pool
Air Conditioning
Fireplace
Waterfront
Oven
Dishwasher
Furnished
Other spaces
Workspace, Kitchen
Cape Cod Bed and Bath
10
Excellent
·
Stevensville
·
1 br
·
Sleeps 2
·
Air Conditioning · In Unit Laundry · Furnished ·
From
$145/nightProperty
House · 1 Bed · 1 bath
Amenities
Air Conditioning
In Unit Laundry
Furnished
Wifi
Best Western Kent Narrows Inn
7.6
Very good
·
Grasonville
·
Studio
·
Sleeps 4
·
On Site Laundry · Assigned Parking · Smoking Allowed ·
From
$81/nightProperty
Hotel · Studio
Amenities
On Site Laundry
Assigned Parking
Smoking Allowed
Carpet
Hot Tub
Free Parking
Pool
Air Conditioning
Other spaces
Workspace, Balcony
Hilton Garden Inn Kent Island
8.5
Very good
·
Grasonville
·
1 br
·
Sleeps 5
·
On Site Laundry · Smoking Allowed · Carpet ·
From
$103/nightProperty
Hotel · 1 Bed
Amenities
On Site Laundry
Smoking Allowed
Carpet
Hot Tub
Free Parking
Pool
Air Conditioning
Furnished
Other spaces
Workspace, Balcony
The Inn at Chesapeake Bay Beach Club
9.3
Excellent
·
Stevensville
·
1 br
·
Sleeps 4
·
On Site Laundry · Assigned Parking · Carpet ·
From
$179/nightProperty
Hotel · 1 Bed
Amenities
On Site Laundry
Assigned Parking
Carpet
Free Parking
Pool
Air Conditioning
Fireplace
Furnished
Other spaces
Workspace
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
10
Excellent
·
Stevensville
·
3 br
·
Sleeps 6
·
Ski In Ski Out · Hot Tub · Ev Charging ·
From
$957/nightProperty
House · 3 Beds · 4 baths
Amenities
Ski In Ski Out
Hot Tub
Ev Charging
Pool
Private Pool
Air Conditioning
Fireplace
Waterfront
Other spaces
Balcony, Kitchen
Wye River Cape
9.9
Excellent
·
Queenstown
·
3 br
·
Sleeps 6
·
Pool · Fitness Center · Private Pool ·
From
$400/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Pool
Fitness Center
Private Pool
Air Conditioning
Fireplace
Waterfront
Oven
Dishwasher
Other spaces
Kitchen
Gorgeous, waterfront 3-bedroom cottage on Wye River - dog friendly
10
Excellent
·
Queenstown
·
3 br
·
Sleeps 7
·
Air Conditioning · Fireplace · Waterfront ·
From
$425/nightProperty
House · 3 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Waterfront
Oven
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Waterfront Getaway - View of bay from your bed
10
Excellent
·
Stevensville
·
1 br
·
Ocean · Outdoor Space · Pool ·
From
$199/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Ocean
Pool
Private Pool
Air Conditioning
Waterfront
Furnished
In Unit Laundry
Wifi
Updated: March 28, 2023
Learn about vacation rentals in
Chester
Explore 3 vacation rentals near Chester, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chester, you can see photos of Chester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chester vacation rentals in specific areas. Whether you’re looking for a Chester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chester is $395 per night and the highest price is $868 per night.
2 of the vacation rentals near Chester are houses.
The average bathroom count for a vacation house near Chester is
3. The average price for vacation houses near Chester is $658 per night. There are 1 vacation homes under this price. The most common
amenities for vacation rentals near Chester are: furnished, outdoor space, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
2 bed rentals
1 available
4+ bed rentals
2 available
Getting around Chester
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Chester
Groceries
3/10
At least one grocery store within a 30-minute walk
Shopping
2/10
Few or no shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Chester, MD FAQ
How many vacation rentals in Chester are available?
There are currently 3 vacation rentals in Chester available. Our vacation rentals in Chester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Chester?
Yes, right now there are 1 pet friendly vacation rentals in Chester. A pet friendly vacation rental in Chester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Chester with a pool?
Yes there are vacation rentals with a pool available in Chester, MD. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Chester with internet access?
As of March 28, 2023, there are vacation rentals with internet access available in Chester, Maryland. Check out more enjoyable destinations on Vacations by Zumper.
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