Search Vacation Homes in Chesapeake City

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 160 Vacation Homes in Chesapeake City with updated reviews, rates, and availability.

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Beautiful Colonial Style Home in Nottingham PA
Fridge, microwave, oven, stovetop

Beautiful Colonial Style Home in Nottingham PA

9.8 out of 10, Exceptional, (11)
"Wonderful experience in a beautiful home. Could live there! Perfect for our entire family. Appreciate how well appointed it was with supplies, linens, etc. Could have used one more bathroom but it didn't cramp our style. Thanks to the host for a memorable vacation! "
Beautiful Colonial Style Home in Nottingham PA
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

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

The price is AED 511
AED 607 total
includes taxes & fees
27 May - 28 May
Charming 2-bedroom house with WiFi, AC in marvelous 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

9.8 out of 10, Exceptional, (13)
"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
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
14 May - 15 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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, (37)
"This 3 bedroom, 2 bath Cottage was perfect! Our family enjoyed staying there. We found the home to be clean, well equipped and comfortable."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,319
AED 2,398 total
includes taxes & fees
13 May - 14 May
5-bedroom vacation home 5 minutes from historic Charlestown
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, (16)
Tip Of The Town Fresh and New 3 Bedroom Nest
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.

9.8 out of 10, Exceptional, (13)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Fridge, microwave, oven, stovetop

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

8.2 out of 10, Very Good, (12)
"The house had plenty of space and location was great!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (18)
"The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions. "
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Cozy 2-bedroom townhome in charming Elkton
Fridge, microwave, oven, stovetop

Cozy 2-bedroom townhome in charming Elkton

9.0 out of 10, Wonderful, (2)
"This home wss a perfect stay for me and my friends, spacious, clean, and as described "
The price is AED 422
AED 526 total
includes taxes & fees
19 May - 20 May
Cozy 2-bedroom townhome in charming Elkton
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
Beautiful Brick-Wall House in Historic Newcastle
Fridge, microwave, oven, stovetop

Beautiful Brick-Wall House in Historic Newcastle

8.0 out of 10, Very Good, (11)
"convenient to northern Delaware and southeastern PA attractions"
Beautiful Brick-Wall House in Historic Newcastle
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, (33)
"The house was great for a girls weekend and the host was very communicative and helpful with finding places to eat/drink as we weren’t familiar with the area. "
Beachfront Sunsets on the Water at Oakwood Beach
Nancy’s Touch, A Waterfront Paradise!
Property grounds

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"This was a great Property, with a Great View. Wife & her sister, and 98yr old Mother really enjoyed it."
Nancy’s Touch, A Waterfront Paradise!
Amazing Waterfront Home on the Bush River
Terrace/patio

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River
White Clay Creek Cottage
Terrace/patio

White Clay Creek Cottage

10.0 out of 10, Exceptional, (4)
"Perfect cottage stay and convenient proximity to Newark DE, Christiana, Longwood Gardens, PA. The owners are very accommodating. Extremely comfortable beds, sofas, and nicely appointed. "
White Clay Creek Cottage
Wilmington Comfort 4 Min to Riverfront fenced yard
Fridge, microwave, oven, stovetop

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (20)
"Good location in downtown Wilmington that works well for a small group looking for a good alternative to nearby Riverfront hotels. "
Wilmington Comfort 4 Min to Riverfront fenced yard
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, (56)
"Host was excellent making sure we had everything we needed and more for a comfortable stay. The home was very cozy and comfortable like being in your own home. We will definitely be returning! "
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
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.
Don't see what you're looking for?
See all available properties in Chesapeake City
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesapeake City

Historic Chesapeake City Stay
Pool

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AED 441
AED 1,059 total
includes taxes & fees
26 May - 27 May
Historic Chesapeake City Stay
Chesapeake City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (14)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City
Terrace/patio

Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time staying here. The inside is so cute and comfortable. Location is great and the host is very quick to respond and accommodate requests. 10/10 "
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City
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.