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

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!

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (15)
"We had a nice stay. Lisa was fantastic at communicating with us and answering any questions we had. The house was very clean and well stocked for our needs. "
The price is SAR 619
SAR 770 total
includes taxes & fees
3 Feb - 4 Feb
New Construction townhome close to everything downtown w/transparent pricing

Cozy 5 bedroom house with attached guest suite

Cozy 5 bedroom house with attached guest suite

Beautiful Brick-Wall House in Historic Newcastle

7.6 out of 10, Good, (10)
"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

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (31)
"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

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

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (7)
"Very clean house. Great rooms, would stay again "
Spacious North East Home w/ Fenced Yard & Fire Pit

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

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (34)
"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

Clean Sanitized upscale suite. One or two beds. Private Bath

9.4 out of 10, Exceptional, (10)
"Had a great stay. Host was very communicative and check in was a breeze. There’s a main bedroom with a tv and couch mini fridge coffee maker and microwave, a bathroom and then a side room with a couch (with a pull out bed) and tv. My only criticism is that the second room is attached to a shared kitchen with only a curtain for separation. If it had been a lockable door on our end it would be a perfect stay. "
The price is SAR 315
SAR 551 total
includes taxes & fees
3 Feb - 4 Feb
Clean Sanitized upscale suite. One or two beds. Private Bath

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

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

9.0 out of 10, Wonderful, (12)
"Easy to locate & use street parking. The neighborhood seemed a bit rough, most neighbors were welcoming. 3 large bedrooms rare find at this pricepoint. The bed were fine but springs poked a bit. were poking and not super comfy. "
Super cute 3 bedroom remodeled townhouse near downtown Wilmington

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

9.6 out of 10, Exceptional, (7)
"Awesome three weeks"
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Welcome to Your Perfect Getaway! Close to Wilmington, Newark, and Philadelphia!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Stayed here with my 84 year old father and 4 teenagers. Dad enjoyed his space on the entry level, which also had it own half bath and thermostat. The rest of us had plenty of room upstairs. The location was great. We were able to get to our family in Wilmington in 20 minutes. The river park was merely a 5 minute walk away and the teenagers enjoyed it very much.....I felt it was safe enough for them to walk by themselves. The management was alsi very easy to communicate with. If we...
Welcome to Your Perfect Getaway! Close to Wilmington, Newark, and Philadelphia!

This house is a 3 bedroom(s), 2 bathrooms, located in Havre de Grace, MD.

10.0 out of 10, Exceptional, (1)
"We had a blast. The home is so beautiful, perfect location. Wonderful homeowners who are very kind. We will definitely be staying again. Thank you. "
This house is a 3 bedroom(s), 2 bathrooms, located in Havre de Grace, MD.

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (13)
"This home is beautifully decorated, making it most inviting and pleasant. The view of the bay was magical! Sitting on the sun porch was so wonderful! The kitchen was the most well equipped kitchen I’ve had the pleasure to use! Thank you for an amazing stay!!"
Upper Chesapeake Getaway - Newly Renovated

Charming 3-bedroom house with AC and WiFi in fabulous Newark

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a perfect place for family to stay during our wedding. The house was very clean and very well maintained. Would definitely recommend to anyone. Thanks again for letting us use your home. "
Charming 3-bedroom house with AC and WiFi in fabulous Newark

Convenient, spacious 3BR 2.5BA WITH PARKING

10.0 out of 10, Exceptional, (1)
"Very nice townhouse close to lots of stores and restaurants."
Convenient, spacious 3BR 2.5BA WITH PARKING

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"Property was as described and according to photos. Children’s toys only consisted of card games, and there was no children’s dinnerware which was listed as provided. Kitchen was not well stocked, as there were no baking supplies and we needed to use the oven. Beds were comfortable and there was ample bedding, pillows, blankets, and towels. There was ample parking. Ceiling fans were amazingly quiet and appreciated in each room. Was difficult to use showers only for children’s baths. Property...
Your perfect Maryland escape awaits!
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

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 1,089 total
includes taxes & fees
1 Mar - 2 Mar
Historic Chesapeake City Stay

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
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.