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Compare 139 Vacation Homes in Chesapeake City with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (257)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

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

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

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

9.8 out of 10, Exceptional, (9)
"The property manager was friendly and eager to help. My husband and son stayed at a rental home in Delaware while they were there for a competition. They found the house to be cozy and tidy. However, they felt that the neighborhood didn't seem safe or welcoming. They were thankful to have a secure place to stay during their trip."
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 1,050 total
includes taxes & fees
3 Apr - 4 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (36)
"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

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
31 Mar - 1 Apr
5-bedroom vacation home 5 minutes from historic Charlestown

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (11)
"Clean and comfortable "
The price is SAR 619
SAR 1,292 total
includes taxes & fees
31 Mar - 1 Apr
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, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

8.8 out of 10, Excellent, (11)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

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
30 Mar - 31 Mar
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Cozy 2-bedroom townhome in charming Elkton

8.0 out of 10, Very Good, (1)
"The house itself was clean. Had everything we needed. It seemed like the back yard was still being cleared of trees and debris. Was too chilly for sitting out though. All and all, was fine."
The price is SAR 431
SAR 537 total
includes taxes & fees
31 Mar - 1 Apr
Cozy 2-bedroom townhome in charming Elkton

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

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (33)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
Beachfront Sunsets on the Water at Oakwood Beach

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at Ted’s property. The basement was cold as they hadn’t figured out to adjust the thermostat yet, so we didn’t spend any time down there. We also encountered challenges with the hot water heater, but overall it was a lovely stay. "
Amazing Waterfront Home on the Bush River

White Clay Creek Cottage

10.0 out of 10, Exceptional, (2)
"Perfect cottage stay and convenient proximity to Newark DE, Christiana, Longwood Gardens, PA. The owners are very accommodating. Extremely comfortable beds, sofas, and nicely appointed. "
White Clay Creek Cottage

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

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!
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

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 1,093 total
includes taxes & fees
31 Mar - 1 Apr
Historic Chesapeake City Stay

Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was an abundant blessing. The hot tub was just the added bonus for those chilly winter evenings. Communication with Jon was superb and his kindness and consideration go above and beyond a 5 Star review!!! Thanks for allowing our family an awesome Christmas!! We can’t wait to be back!!"
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home 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
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.