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Vacation Homes in Chesapeake City

Our top choices for Chesapeake City vacation 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

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

9.6 out of 10, Exceptional, (62)
"Cozy place that was fine for the 2 of us and 2 dogs.Fenced yard was great.Fun downtown that we walked many times.Jamies Donut shop is a must stop."
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (53)
"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

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 SAR 375
SAR 467 total
includes taxes & fees
23 Sep - 24 Sep
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

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

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

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

9.6 out of 10, Exceptional, (22)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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!

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!

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (21)
"We had a wonderful stay in Chesapeake City! The property was very clean, well stocked, and perfect for our family. The kitchen is gorgeous with a beautiful view of the water, and everything is labeled so items are easy to find and put away. Just a short walk to dinner at Schaefer’s Canal House and the trail. Highly recommend!"
Chesapeake City Quiet Overlook

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (17)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
The price is SAR 596
SAR 837 total
includes taxes & fees
28 Sep - 29 Sep
New Construction townhome close to everything downtown w/transparent pricing

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, (2)
"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

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake

Luxury Waterfront Home Built for Entertaining!

5.0 out of 10, (2)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
The price is SAR 1,857
SAR 3,117 total
includes taxes & fees
23 Sep - 24 Sep
Luxury Waterfront Home Built for Entertaining!

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (5)
"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 SAR 367
SAR 671 total
includes taxes & fees
25 Sep - 26 Sep
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 SAR 506
SAR 1,280 total
includes taxes & fees
25 Sep - 26 Sep
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

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

9.2 out of 10, Wonderful, (179)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
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