Chesapeake Vacation Rentals
PRICE PER NIGHT
ACCOMMODATION TYPES
Stunning waterfront villa, indoor pool, kids swingset
10
Excellent
·
Apartment
·
6 br
·
Sleeps 18
·
Ev Charging · Balcony · Hot Tub ·
From
$1,195/nightProperty
Apartment · 6 Beds · 6 baths
Amenities
Ev Charging
Hot Tub
Private Pool
Fireplace
Pool
Dishwasher
Oven
Wifi
Other spaces
Balcony, Workspace, Kitchen
Lacana Aleka
No reviews
·
Apartment
·
1 br
·
Sleeps 6
·
Assigned Parking · Balcony · Free Parking ·
From
$144/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
Assigned Parking
Free Parking
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Fairfield by Marriott Inn & Suites Middletown
9.2
Excellent
·
Hotel
·
1 br
·
Sleeps 4
·
Furnished ·
From
$157/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Welcome to The Richfield!
No reviews
·
Apartment
·
4 br
·
Sleeps 10
·
Assigned Parking · Free Parking · Dishwasher ·
From
$280/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Assigned Parking
Free Parking
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Staybridge Suites Wilmington Downtown, an IHG Hotel
9.2
Excellent
·
Hotel
·
1 br
·
Sleeps 5
·
Workspace · Air Conditioning · Furnished ·
From
$176/nightProperty
Hotel · 1 Bed
Amenities
Air Conditioning
Furnished
Fitness Center
Other spaces
Workspace
Winter sale! Near route 1, I95 and Olgetown Staton RD.
No reviews
·
House
·
Studio
·
Sleeps 4
·
Fireplace · Workspace · Oven ·
From
$161/nightProperty
House · Studio · 2 baths
Amenities
Fireplace
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
NEW! Wilmington Apartment: Day Trip to Dtwn Philly
No reviews
·
Apartment
·
4 br
·
Sleeps 8
·
Central Heat · Ceiling Fan · Dishwasher ·
From
$164/nightProperty
Apartment · 4 Beds · 1 bath
Amenities
Central Heat
Ceiling Fan
Dishwasher
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Historic Creekside Home - 2br 2.5ba - Downtown North East
10
Excellent
·
House
·
2 br
·
Sleeps 6
·
Hardwood Floor · On Site Laundry · Dishwasher ·
From
$158/nightProperty
House · 2 Beds · 3 baths
Amenities
Hardwood Floor
On Site Laundry
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
The best of Zumper, delivered
Be the first to hear about new listings matching your search.
Unobstructed view of the Chesapeake Bay, w/ a beach!
10
Excellent
·
Condo
·
3 br
·
Sleeps 6
·
Ev Charging · Ceiling Fan · Deck ·
From
$215/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Ev Charging
Ceiling Fan
Beach
Waterfront
Pool
Dishwasher
Oven
Wifi
Other spaces
Deck, Balcony, Workspace, Kitchen
Hyatt Place Newark-Main Street
No reviews
·
Hotel
·
1 br
·
Sleeps 6
·
Furnished ·
From
$179/nightProperty
Hotel · 1 Bed
Amenities
Furnished
Private Waterfront Estate with Pool, Private Beach and Dock
10
Excellent
·
House
·
7 br
·
Sleeps 18
·
Hot Tub · Private Pool · Beach ·
From
$1,237/nightProperty
House · 7 Beds · 5 baths
Amenities
Hot Tub
Private Pool
Beach
Waterfront
Pool
Dishwasher
Oven
Wifi
Other spaces
Kitchen
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
9.6
Excellent
·
Apartment
·
3 br
·
Sleeps 6
·
Hot Tub · Waterfront · Outdoor Space ·
From
$282/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
Hot Tub
Waterfront
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
BEACH WITHOUT THE BUSTLE
9.8
Excellent
·
Condo
·
2 br
·
Sleeps 6
·
Ev Charging · Deck · Balcony ·
From
$196/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Ev Charging
Beach
Pool
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Other spaces
Deck, Balcony, Workspace, Kitchen
Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft
9.3
Excellent
·
House
·
4 br
·
Sleeps 16
·
Walk In Closets · Hot Tub · Private Pool ·
From
$674/nightProperty
House · 4 Beds · 7 baths
Amenities
Walk In Closets
Hot Tub
Private Pool
On Site Laundry
Fireplace
Waterfront
Pool
Dishwasher
Other spaces
Kitchen
Five Bedroom Villa & Pool on North East Harbor
No reviews
·
Apartment
·
5 br
·
Sleeps 10
·
Central Heat · Balcony · Private Pool ·
From
$671/nightProperty
Apartment · 5 Beds · 5 baths
Amenities
Central Heat
Private Pool
On Site Laundry
Free Parking
Pool
Dishwasher
Oven
Wifi
Other spaces
Balcony, Kitchen
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
No reviews
·
House
·
4 br
·
Sleeps 8
·
Dishwasher · Workspace · Oven ·
From
$248/nightProperty
House · 4 Beds · 4 baths
Amenities
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Home away from home between Wilmington/Newark
No reviews
·
Apartment
·
3 br
·
Sleeps 4
·
On Site Laundry · Kitchen · In Unit Laundry ·
From
$243/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
On Site Laundry
In Unit Laundry
Furnished
Other spaces
Kitchen
Charming Cottage in Historic Charlestown, MD - Marina & Beach Access
9.8
Excellent
·
House
·
3 br
·
Sleeps 8
·
Deck · Outdoor Space · Wifi ·
From
$317/nightProperty
House · 3 Beds · 2 baths
Amenities
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Deck, Kitchen
Bonfire by the Creek!!!
9.6
Excellent
·
House
·
3 br
·
Sleeps 5
·
Fitness Center · Waterfront · Outdoor Space ·
From
$253/nightProperty
House · 3 Beds · 2 baths
Amenities
Fitness Center
Waterfront
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
Stunning modern 2 BD apt close to Christiana Hosp
No reviews
·
Apartment
·
2 br
·
Sleeps 5
·
On Site Laundry · Dishwasher · Kitchen ·
From
$93/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
On Site Laundry
Dishwasher
Furnished
Other spaces
Kitchen
Wilmington Apartment Day Trip to Dtwn Philly
No reviews
·
Apartment
·
4 br
·
Sleeps 8
·
Free Parking · Wifi · Kitchen ·
From
$230/nightProperty
Apartment · 4 Beds · 1 bath
Amenities
Free Parking
Wifi
Furnished
Other spaces
Kitchen
Professionally Cleaned Waterfront Property! - Dock, Beach,Bungalows & Boat Lift
9.9
Excellent
·
House
·
7 br
·
Sleeps 15
·
Beach · Fireplace · Waterfront ·
From
$730/nightProperty
House · 7 Beds · 7 baths
Amenities
Beach
Fireplace
Waterfront
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
A European styled retreat on Marylands Eastern Shore with Private pool
9.6
Excellent
·
House
·
3 br
·
Sleeps 8
·
Private Pool · Fireplace · Outdoor Space ·
From
$368/nightProperty
House · 3 Beds · 3 baths
Amenities
Private Pool
Fireplace
Pool
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Prime Location! Pet-Friendly Property, Free Parking, Onsite Indoor Pool
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$114/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Parking
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$124/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Pool
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$114/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Convenient Stay in Delaware! Free Parking, Pool, Pets Allowed
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$124/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Your Home Away From Home! Onsite Pool, Free Parking, Pets Allowed
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$114/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Just What You Were Looking For! Onsite Pool, Free Parking, Pets Allowed
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$124/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Worlds End Chesapeake Cottage
10
Excellent
·
Apartment
·
2 br
·
Sleeps 4
·
Fireplace · Waterfront · Outdoor Space ·
From
$238/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fireplace
Waterfront
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Charming 5 bed Mountain Home in National Preserve. Romantic peaceful getaway nea
10
Excellent
·
Apartment
·
3 br
·
Sleeps 8
·
Hardwood Floor · Deck · Wifi ·
From
$570/nightProperty
Apartment · 3 Beds · 3 baths
Amenities
Hardwood Floor
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Deck
Riverfront Retreat with panoramic water views and breathtaking sunsets.
9.4
Excellent
·
House
·
7 br
·
Sleeps 14
·
Hot Tub · Private Pool · Fireplace ·
From
$1,333/nightProperty
House · 7 Beds · 5 baths
Amenities
Hot Tub
Private Pool
Fireplace
Waterfront
Pool
Dishwasher
Oven
Wifi
Other spaces
Kitchen
Relaxing Ranch with 1 king and 2 queens, fast WiFi
No reviews
·
House
·
3 br
·
Sleeps 6
·
Wifi · Kitchen · In Unit Laundry ·
From
$284/nightProperty
House · 3 Beds · 2 baths
Amenities
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Vintage Waterfront Cottage with Stunning Sunsets
No reviews
·
Apartment
·
2 br
·
Sleeps 4
·
Beach · Fireplace · Waterfront ·
From
$415/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Beach
Fireplace
Waterfront
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
College Park Comfort - 4 mins from University of DE
9.3
Excellent
·
House
·
3 br
·
Sleeps 6
·
Pool · Workspace · Oven ·
From
$150/nightProperty
House · 3 Beds · 1 bath
Amenities
Pool
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Swimming Pool
Other spaces
Workspace, Kitchen
Clean and Cozy 2 BR home blocks away from downtown
10
Excellent
·
House
·
2 br
·
Sleeps 6
·
Dishwasher · Workspace · Oven ·
From
$167/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
The White House on North East Harbor
No reviews
·
House
·
4 br
·
Sleeps 8
·
Assigned Parking · Furnished ·
From
$719/nightProperty
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Furnished
NEW! Family-Friendly Cottage, Walk to the Beach!
10
Excellent
·
House
·
2 br
·
Sleeps 6
·
Microwave · Toiletries · Tv ·
From
$155/nightProperty
House · 2 Beds · 1 bath
Amenities
Microwave
Toiletries
Tv
Central Heat
Ceiling Fan
Walk In Closets
Free Parking
Fireplace
Other spaces
Kitchen
Waterfront with Chesapeake Sunsets
9.9
Excellent
·
House
·
3 br
·
Sleeps 8
·
Beach · Fireplace · Waterfront ·
From
$213/nightProperty
House · 3 Beds · 3 baths
Amenities
Beach
Fireplace
Waterfront
Dishwasher
Oven
Wifi
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Quiet & Private with Fire Pit Out Back!
9.6
Excellent
·
House
·
3 br
·
Sleeps 6
·
Fitness Center · Oven · Wifi ·
From
$275/nightProperty
House · 3 Beds · 1 bath
Amenities
Fitness Center
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
Private Master Bed, Bath, and Walk-in Closet
No reviews
·
House
·
1 br
·
Sleeps 2
·
Walk In Closets · On Site Laundry · Kitchen ·
From
$75/nightProperty
House · 1 Bed · 2 baths
Amenities
Walk In Closets
On Site Laundry
Furnished
Other spaces
Kitchen
Comfy space near University of Delaware
No reviews
·
Apartment
·
3 br
·
Sleeps 7
·
On Site Laundry · Free Parking · Dishwasher ·
From
$147/nightProperty
Apartment · 3 Beds · 1 bath
Amenities
On Site Laundry
Free Parking
Dishwasher
Oven
Wifi
Air Conditioning
Furnished
Storage
Other spaces
Workspace, Kitchen
NEW! Wilmington Apartment: Day Trip to Dtwn Philly
No reviews
·
Apartment
·
4 br
·
Sleeps 8
·
Cable · Toiletries · Tv ·
From
$145/nightProperty
Apartment · 4 Beds · 1 bath
Amenities
Cable
Toiletries
Tv
Ceiling Fan
Walk In Closets
Free Parking
Wifi
Other spaces
Kitchen
Boho Serenity Convenient, Fast Wi-fi 3BR 1.5Ba TH
No reviews
·
House
·
3 br
·
Sleeps 8
·
Workspace · Oven · Wifi ·
From
$189/nightProperty
House · 3 Beds · 2 baths
Amenities
Oven
Wifi
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Oaxaca, a private room with private entrance
10
Excellent
·
House
·
1 br
·
Sleeps 3
·
Wifi · In Unit Laundry · Air Conditioning ·
From
$60/nightProperty
House · 1 Bed · 1 bath
Amenities
Wifi
In Unit Laundry
Air Conditioning
Furnished
University Delaware Museums Tour! Family-friendly Accommodation! Parking is FREE
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$116/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
A Short Drive from the University of Delaware Botanic Gardens! Pets Allowed!
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$116/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Close to Downtown Wilmington and the University of Delaware! FREE Parking, Pool!
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$122/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
Minutes Away from Newark Reservoir! Pets Allowed, FREE Parking, Indoor Pool!
No reviews
·
House
·
1 br
·
Sleeps 2
·
Pool · Workspace · In Unit Laundry ·
From
$117/nightProperty
House · 1 Bed · 1 bath
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Concierge Service
Fitness Center
Swimming Pool
Business Center
Other spaces
Workspace
HOME SWEET HOME in the heart of Wilmington. Entire place with private parking
9.3
Excellent
·
Apartment
·
1 br
·
Sleeps 3
·
Assigned Parking · Workspace · Wifi ·
From
$87/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Assigned Parking
Wifi
Air Conditioning
Furnished
Business Center
Other spaces
Workspace, Kitchen
Showing 1 - 50 of 207 results
Updated: March 22, 2023
Learn about vacation rentals in
Chesapeake
Discover 210 vacation rentals near Chesapeake, Maryland. This lake community is a good place to getaway, relax, and enjoy the outdoors. Explore nature in this lakeside area. Use our interactive map to find Chesapeake properties near the lake. Whether you’re looking for a nightly rental, 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 near Chesapeake is $60 per night and goes up to as much as $1,333 per night.
44 of the vacation rentals near Chesapeake are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $155 per night. There are
currently 28 vacation units under this
price. 99 of the vacation rentals near Chesapeake are houses.
The average bathroom count for a vacation house near Chesapeake is
2. The average price for vacation houses near Chesapeake is $298 per night. There are 61 vacation homes under this price. The most common
amenities for vacation rentals near Chesapeake are: furnished, air conditioning, and in-unit laundry. 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
94 available
2 bed rentals
34 available
3 bed rentals
46 available
4+ bed rentals
32 available
Getting around Chesapeake
Walking
1/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Chesapeake
Groceries
0/10
No grocery stores within walking distance
Shopping
0/10
Few or no shops within walking distance
Cafes
0/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Parks
5/10
Moderate amount of park space nearby
Nightlife
3/10
Few or no bars within walking distance
Chesapeake Vacation Rentals FAQ
How many Chesapeake vacation rentals are available?
As of March 22, 2023, there are 210 Chesapeake vacation rentals available. Use the filters on Vacations by Zumper to find your next Chesapeake vacation spot.
Are there vacation rentals near Chesapeake that have more than 2 bedrooms?
Currently, there are 112 vacation rentals near Chesapeake 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 vacation rentals have internet access?
There are currently 172 Chesapeake 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 have more than 1 bathroom?
Right now, there are 167 vacation rentals near Chesapeake that have more than 1 bathroom. View vacation spots and check availability for different properties today.
Are there any pet friendly Chesapeake vacation rentals?
As of March 22, 2023, there are 83 pet friendly vacation rentals near Chesapeake. Pet friendly rental policies are managed by the owner. We recommend contacting the listing agent for dog, cat, and other pet policies.
More Options
Compare over 500K vacation listings
Search in one place
Our marketplace is populated with rentals from trusted partners like Vrbo, Booking.com, and more, so you can search a wide selection on a single platform.
