Holiday Homes in Chesapeake City

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Featured Holiday Homes in Chesapeake City

Our top choices for Chesapeake City holiday homes

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"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

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

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

9.6 out of 10, Exceptional, (62)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (40)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (18)
"Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group."
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

10.0 out of 10, Exceptional, (1)
"The property is exactly as you see in the pictures/description. We were 4 adults, 4 kids (9 months to 13 years). Plenty of room for all of us. Hosts were quick to respond to any messages sent.Had a great 3 days here."
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

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."
The price is AU$244
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

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

9.6 out of 10, Exceptional, (22)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

9.2 out of 10, Wonderful, (179)
"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

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (2)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

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

Waterfront Lodge packed with Amenities

10.0 out of 10, Exceptional, (1)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
Waterfront Lodge packed with Amenities

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (143)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is AU$855
includes taxes & fees
9 Sept - 10 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (273)
"Beautiful home and setting!"
Captivating Chesapeake experience

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is AU$258
includes taxes & fees
7 Sept - 8 Sept
Summer Rustic Camping with AC and King Bed

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
The price is AU$580
includes taxes & fees
15 Sept - 16 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

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

9.8 out of 10, Exceptional, (19)
"We rented this townhouse for a month for my son's surgical residency rotation at Cristiana Care. It was a perfect location and easy to get to and from the hospital. Owner was very responsive with any questions / concerns which we appreciated. Very quiet and close to grocery stores. Even had a Trader Joe's close by!"
The price is AU$507
includes taxes & fees
14 Sept - 15 Sept
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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

10.0 out of 10, Exceptional, (2)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
The price is AU$499
includes taxes & fees
7 Sept - 8 Sept
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
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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Top Chesapeake City Hotel Reviews

Find out more about Chesapeake City

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Chesapeake City Holiday Homes information

Number of reviews
Accommodation
166 Holiday Homes
Lowest Price
AU$244
Highest Price
AU$855