Chesapeake Bay Vacation Rentals
PRICE PER NIGHT
ACCOMMODATION TYPES
“Wit’s End” at Bayford, VA: Large Waterfront House on Virginia’s Eastern Shore
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Free Parking · Workspace · Balcony ·
From
$594/nightProperty
House · 3 Beds · 4 baths
Amenities
Free Parking
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Balcony, Kitchen
Cheerful Creekside Home with Dock
8.8
Very good
·
House
·
3 br
·
Sleeps 7
·
Balcony · Waterfront · Dishwasher ·
From
$225/nightProperty
House · 3 Beds · 2 baths
Amenities
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Wheelchair Accessible
Other spaces
Balcony, Kitchen
Waterfront Home - Private Pier, Kayaks, Fishing, Beautiful Sunrises and Sunsets!
9.8
Excellent
·
House
·
4 br
·
Sleeps 8
·
Deck · Beach · Waterfront ·
From
$273/nightProperty
House · 4 Beds · 2 baths
Amenities
Beach
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Deck, Kitchen
Feed Your Soul at Silver Beach Cove
9.9
Excellent
·
Apartment
·
3 br
·
Sleeps 6
·
High Ceilings · Fitness Center · Fireplace ·
From
$330/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
High Ceilings
Fitness Center
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!
9.7
Excellent
·
House
·
4 br
·
Sleeps 12
·
Balcony · Beach · Fireplace ·
From
$758/nightProperty
House · 4 Beds · 4 baths
Amenities
Beach
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
3 Bedroom Bay Home with Private Dock & all the Amenities
No reviews
·
Apartment
·
3 br
·
Sleeps 8
·
Hardwood Floor · Hot Tub · Assigned Parking ·
From
$292/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Hardwood Floor
Hot Tub
Assigned Parking
Ocean
Free Parking
Fireplace
Waterfront
Dishwasher
Other spaces
Workspace, Balcony, Kitchen
Piper's Landing 2 Bedroom Beach House near The Chesapeake Bay
8
Very good
·
Apartment
·
3 br
·
Sleeps 6
·
Assigned Parking · Free Parking · Fireplace ·
From
$98/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Assigned Parking
Free Parking
Fireplace
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Share Splendid Sunsets Over the Beautiful Chesapeake Bay!
9.6
Excellent
·
Apartment
·
2 br
·
Sleeps 5
·
Outdoor Space · Oven · Air Conditioning ·
From
$153/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Residents Lounge
Other spaces
Kitchen
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3 BR Bay Home w Private Dock & all the Amenities
10
Excellent
·
Apartment
·
3 br
·
Sleeps 8
·
Workspace · Outdoor Space · Dishwasher ·
From
$225/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Garage Parking
Residents Lounge
Other spaces
Workspace, Kitchen
The Farmhouse at Chatham Vineyards
10
Excellent
·
House
·
3 br
·
Sleeps 5
·
Workspace · Waterfront · Outdoor Space ·
From
$220/nightProperty
House · 3 Beds · 2 baths
Amenities
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Wheelchair Accessible
Other spaces
Workspace, Kitchen
*SANDY HILL SUNSETS*
9.9
Excellent
·
Apartment
·
1 br
·
Sleeps 4
·
Coffee Tea Maker · Smoking Allowed · Beach ·
From
$167/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Coffee Tea Maker
Smoking Allowed
Beach
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Historic Waterfront Home With Big Views Of The Chesapeake Bay
10
Excellent
·
House
·
3 br
·
Sleeps 6
·
Ceiling Fan · Balcony · Fireplace ·
From
$250/nightProperty
House · 3 Beds · 3 baths
Amenities
Ceiling Fan
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Sun & Sand Private Breathtaking beachfront home, DRAMATIC VIEWS AND SUNSETS
9.7
Excellent
·
House
·
4 br
·
Sleeps 12
·
On Site Laundry · Balcony · Beach ·
From
$600/nightProperty
House · 4 Beds · 4 baths
Amenities
On Site Laundry
Beach
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Relax and Renew on your private deck overlooking the Chesapeake Bay
9.8
Excellent
·
Apartment
·
2 br
·
Sleeps 4
·
Beach · Waterfront · Outdoor Space ·
From
$145/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Waterfront
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Garage Parking
Other spaces
Kitchen
Modern House on a Private Beach - Relax in Paradise with OBX like environment.
9.6
Excellent
·
House
·
4 br
·
Sleeps 10
·
Ev Charging · Pool · Ocean ·
From
$665/nightProperty
House · 4 Beds · 4 baths
Amenities
Ev Charging
Pool
Ocean
Beach
Fireplace
Waterfront
Dishwasher
Oven
Other spaces
Kitchen
Cozy Waterfront Escape Where Pets Stay For Free!
9.5
Excellent
·
Apartment
·
2 br
·
Sleeps 6
·
Free Parking · Balcony · Dishwasher ·
From
$274/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Storage
Other spaces
Balcony, Kitchen
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
9.9
Excellent
·
House
·
5 br
·
Sleeps 12
·
Deck · Ocean · Balcony ·
From
$525/nightProperty
House · 5 Beds · 4 baths
Amenities
Ocean
Beach
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Deck, Balcony, Kitchen
Beach House on Chesapeake Bay!
9.9
Excellent
·
House
·
3 br
·
Sleeps 8
·
Fitness Center · Workspace · Fireplace ·
From
$455/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Beachfront Home on Chesapeake Bay - Gwynn’s Island
10
Excellent
·
House
·
3 br
·
Sleeps 8
·
Balcony · Beach · Fireplace ·
From
$350/nightProperty
House · 3 Beds · 4 baths
Amenities
Beach
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
9.9
Excellent
·
Apartment
·
1 br
·
Sleeps 4
·
On Site Laundry · Assigned Parking · Smoking Allowed ·
From
$160/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Assigned Parking
Smoking Allowed
Ocean
Beach
Waterfront
Oven
Air Conditioning
Other spaces
Kitchen
Waterfront Retreat on 4 acres with boat slips.
10
Excellent
·
House
·
3 br
·
Sleeps 8
·
On Site Laundry · Outdoor Space · Air Conditioning ·
From
$242/nightProperty
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Nassawadox Creek Waterfront Home with Private Pool
10
Excellent
·
House
·
3 br
·
Sleeps 8
·
Pool · Smoking Allowed · Fireplace ·
From
$325/nightProperty
House · 3 Beds · 3 baths
Amenities
Pool
Smoking Allowed
Fireplace
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Showing 1 - 22 of 22 results
Updated: March 29, 2023
Learn about vacation rentals in
Chesapeake Bay
Browse 22 vacation rentals near Chesapeake Bay, Maryland. This bay community is a good place to find your next vacation or adventure near the water. Use our interactive map to find Chesapeake Bay properties near the bay. Whether you’re looking for a day trip, weekend getaway, or week long vacation, we’ve got you covered. The lowest vacation rental price near Chesapeake Bay is $98 per night and the highest price is $758 per night. Use the date filters at the top to select your travel dates and view availability.
14 of the vacation rentals near Chesapeake Bay are houses.
The average bathroom count for a vacation house near Chesapeake Bay is
3. The average price for vacation houses near Chesapeake Bay is $399 per night. There are 8 vacation homes under this price. The most common
amenities for vacation rentals near Chesapeake Bay 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.
1 bed rentals
2 available
2 bed rentals
3 available
3 bed rentals
12 available
4+ bed rentals
5 available
Which price range for vacation rentals is considered a good deal in Chesapeake Bay, MD area?
Vacation Rental Price Information in Chesapeake Bay, MD
The graph shows the percentages of vacation homes in each price bucket. Chesapeake Bay, MD has the largest percentage (22.73%) of homes in $500+ price range.
$0 - $50
1
units
$50 - $100
1
units
$100 - $150
3
units
$150 - $200
4
units
$200 - $250
4
units
$250 - $300
2
units
$300 - $350
1
units
$400 - $450
1
units
$500+
5
units
Chesapeake Bay Vacation Rentals FAQ
How many Chesapeake Bay vacation rentals are available?
As of March 29, 2023, there are 22 Chesapeake Bay vacation rentals available. Use the filters on Vacations by Zumper to find your next Chesapeake Bay vacation spot.
Are there vacation rentals near Chesapeake Bay that have more than 2 bedrooms?
Currently, there are 20 vacation rentals near Chesapeake Bay that have more than 2 bedrooms. Check each listing to view photos, pricing, and amenities, and contact the listing manager to begin your next vacation today.
How many Chesapeake Bay vacation rentals have internet access?
There are currently 22 Chesapeake Bay vacation rentals that have internet access. See a full list of property features, photos, pricing, and check availability today.
How many vacation rentals near Chesapeake Bay have more than 1 bathroom?
Right now, there are 22 vacation rentals near Chesapeake Bay that have more than 1 bathroom. View vacation spots and check availability for different properties today.
Are there any pet friendly Chesapeake Bay vacation rentals?
As of March 29, 2023, there are 13 pet friendly vacation rentals near Chesapeake Bay. Pet friendly rental policies are managed by the owner. We recommend contacting the listing agent for dog, cat, and other pet policies.
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