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Vacation Rentals in Chesapeake City, Maryland

about Chesapeake City

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Chesapeake City, Maryland vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Chesapeake City are added and updated every week!

Compared to hotels, Chesapeake City vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Chesapeake City, Maryland Vacation Rentals and Tourism

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Chesapeake City things to do


Go Ape!

I want to start off by saying that I had a blast. It is an aerial obstacle course with a few zip lines and a couple of Tarzan swings. It can definitely more


Home Grown Cafe

Food and Service used to be better. We have eaten at this place multiple times to include events like birthdays, friends from out of town and just the 2 more


The Delaware Rock Gym

So much fun! I've never been rock climbing before and was skeptical about going, but it turned out to be a lot of fun. I went "bouldering," which is a more


Lums Pond State Park

Lots of picnic tables, lots of parking, gazebos to rent. You can also rent boats and kayaks and junk like that. There is also disc golf, and the Go more


University of Delaware Ice Arena

I LOVE this place! I have been there a few times and have always had a blast. The skating rink is pretty big so there is always enough room and it more


Delaware Saengerbund Oktoberfest

I look forward to the main event every year for the past 4 years. Bring your own 1.5l mug and save yourself tons of trips to the beer booth...maybe. Food more


Westown Movies

The accommodations at this movie theater are excellent. Prices are phenomenal, and you get a better theater and more comfortable seating for lower than more


Regal Peoples Plaza Cinema

I like that they have a computerized ticket system, so when the line is long and you are running late to the movie, you can skip the line if you are more


White Clay Creek State Park

Perfect park for trail unning, biking, fishing, birding or just enjoying the more


James F Hall Trail

James F Hall trail is a hidden gem hidden in the city of Newark. At 1.76, the lighted and paved trail runs through Phillips, Lewis, and Kells city parks more


Trilogy Salon & Day Spa Inc

I was in from out of town and needed my last (bad) nail job replaced. I tried Trilogy based on Yelp, and was not disappointed. As I walk in I couldn't more


Charles E. Price Memorial Park At Levels Road

This is a great park. There are two fenced areas for dogs, separated by smaller and larger dogs. Inside the fenced in areas are trees, fire hydrants, more


Bear - Glasgow Family YMCA

Recently joined after cancelling my Planet Fitness membership, looking for an "upgrade" of sorts. The biggest factors here that motivated me to give more


Glasgow Park

If I could give this park ten stars I would. This park has a little bit for everyone. There is a 2.7 mile paved course that circles around the park more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Perfect For Families! Beautiful Views, Waterfront, Pool And So Much More!
Chesapeake City Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • owner badgeowner badge
  • sleeps 13
  • baths 6
  • rates (USD) $825 - $1,750 /nt
    $5,775 - $12,250 /wk
    $21,000 - $36,000 /mth

14 reviews write a review