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Compare 117 Vacation Homes in Chesapeake City with updated reviews, rates, and availability.

Beautiful Colonial Style Home in Nottingham PA

9.6 out of 10, Exceptional, (9)
"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

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (32)
"We had a nice visit to this beautiful, waterfront home, and appreciated the host very much. The views from the beach were lovely. Unfortunately, we were woken several times overnight one night by ships’ foghorns as they passed by- every few hours. Even the white noise machines (a thoughtful touch) didn’t help. Not sure how to predict when the ships come through, but we slept soundly the second of our two nights there. The area is otherwise very quiet- we barely saw anyone else around. The...
Beachfront Sunsets on the Water at Oakwood Beach

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

9.8 out of 10, Exceptional, (9)
"It was fine"
Cozy on the Hill. Close to Riverfront, Brandywine park and great food

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

The price is SAR 506
SAR 1,046 total
includes taxes & fees
9 Mar - 10 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (11)
"Clean, cute little house, convenient location"
The price is SAR 563
SAR 1,225 total
includes taxes & fees
9 Mar - 10 Mar
Tip Of The Town Fresh and New 3 Bedroom Nest

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

9.8 out of 10, Exceptional, (11)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is SAR 2,115
SAR 4,150 total
includes taxes & fees
7 Mar - 8 Mar
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

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

8.0 out of 10, Very Good, (11)
"The location was ideal considering it was located at a reasonable distances to all places I had to go to. Short or moderate drive to about 5 different locations."
Beautiful Brick-Wall House in Historic Newcastle

Clean and Cozy 2 BR home blocks away from downtown

10.0 out of 10, Exceptional, (20)
"Phyllis’ home was 100% newly remodeled and impeccably clean! We enjoyed a wonderful stay in her comfortable home. The fresh flowers were a welcome surprise after a long drive, and Phyllis checked in on us via text to make sure we made it there safely. Recommend! "
Clean and Cozy 2 BR home blocks away from downtown

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (35)
"Our family stayed here for 5 nights. The house was updated and beautiful! It was stocked with all of our basic needs and the owners quickly responded to any questions, as well as provided suggestions for local places to check out. We especially enjoyed hiking area trails, including the lighthouse, and walking and shopping in North East. It was an enjoyable and relaxing stay. Thank you for your hospitality!"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

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

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

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

8.6 out of 10, Excellent, (10)
"The house had plenty of space and location was great!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.

9.8 out of 10, Exceptional, (102)
"House was great yet again. Betsy always has the place clean and ready for us!!"
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (20)
"Host was helpful with great communication. Property was clean, spaceous and pet friendly. Great experience over all. Only negative feedback to provide is the neighborhood did not feel safe. "
Wilmington Comfort 4 Min to Riverfront fenced yard

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 SAR 1,347
SAR 2,449 total
includes taxes & fees
10 Mar - 11 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

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

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

9.4 out of 10, Exceptional, (169)
"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

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub
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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Other property types in Chesapeake City

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (52)
"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"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

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is SAR 450
SAR 1,109 total
includes taxes & fees
16 Mar - 17 Mar
Historic Chesapeake City Stay
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.