Search Vacation Homes in Chesapeake City

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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, (10)
"We had a great stay at this house! It was clean, comfortable and "
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, (11)
"The unit was perfect for our stay. It was spacious and clean. The location was great, close to restaurants and easy access to major roadways."
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 507
SAR 1,050 total
includes taxes & fees
8 Apr - 9 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, (37)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
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 2,450 total
includes taxes & fees
8 Apr - 9 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, (13)
"We had a wonderful get away at a lovely home. It was very clean and decorated nice. We would stay there again. "
The price is SAR 525
SAR 1,185 total
includes taxes & fees
8 Apr - 9 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 2,116
SAR 4,152 total
includes taxes & fees
8 Apr - 9 Apr
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 432
SAR 537 total
includes taxes & fees
9 Apr - 10 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, (3)
"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.
Don't see what you're looking for?
See all available properties in Chesapeake City
Save an average of 15% on thousands of hotels when you're signed in

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 1,094 total
includes taxes & fees
8 Apr - 9 Apr
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.