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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Chesapeake City

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (261)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (19)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Luxury Waterfront Home Built for Entertaining!
6 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is AED 2,020
AED 3,293 total
includes taxes & fees
23 Jun - 24 Jun
Luxury Waterfront Home Built for Entertaining!
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (174)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (24)
"Very easy to walk to the downtown area and such a lovely property. Will stay here again if we come back to the North East area"
Clean and Cozy 2 BR home blocks away from downtown
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
Miscellaneous

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (87)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,187
AED 2,239 total
includes taxes & fees
1 Jul - 2 Jul
5-bedroom vacation home 5 minutes from historic Charlestown
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (1)
"Never heard from host. Expedia had to cancel reservation."
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
Interior

Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL

Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (17)
"Wonderful experience, thank you for having us!! "
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Modern cozy get-away* game room-amish country
TV, fireplace

Modern cozy get-away* game room-amish country

Modern cozy get-away* game room-amish country
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Smart TV, fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

The price is AED 727
AED 1,043 total
includes taxes & fees
8 Jul - 9 Jul
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.4 out of 10, Exceptional, (46)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (57)
"Great place. Accurately depicted in photos. Nice quiet neighborhood. Super dog friendly!"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (15)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Beachfront Sunsets on the Water at Oakwood Beach
On the beach, sun loungers, beach towels

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (35)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
Beachfront Sunsets on the Water at Oakwood Beach
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
Interior

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

8.4 out of 10, Very Good, (14)
"Amazing stay. nice quiet clean home. Accommodating for the whole family. Host was easy to connect with very helpful loved our stay ! Looking forward to booking again."
Super cute 3 bedroom remodeled townhouse near downtown Wilmington
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Living area

Cozy on the Hill. Close to Riverfront, Brandywine park and great food

9.6 out of 10, Exceptional, (14)
"Perfect place to stay for an extended work trip. The host is responsive, accommodating and was great to work with. "
Cozy on the Hill. Close to Riverfront, Brandywine park and great food
Spacious North East Home w/ Fenced Yard & Fire Pit
Terrace/patio

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (9)
"Was the best option in the area and would use again."
Spacious North East Home w/ Fenced Yard & Fire Pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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