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

Compare 114 Vacation Homes in Chesapeake City with updated reviews, rates, and availability.

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

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (11)
"This was a quick trip to Delaware and Lisa’s place was great. Super cute and thoughtful touches throughout. She communicated well with me. Her place is spacious and offers privacy with two separate bedrooms and bathrooms with an additional half bath downstairs. "
The price is AED 547
AED 665 total
includes taxes & fees
2 Jan - 3 January 2025
New Construction townhome close to everything downtown w/transparent pricing

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

10.0 out of 10, Exceptional, (5)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

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, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (43)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

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

Wilmington Comfort 4 Min to Riverfront fenced yard

9.2 out of 10, Wonderful, (18)
"Great value, was a great jumping point for our group, who was here for a wedding"
Wilmington Comfort 4 Min to Riverfront fenced yard

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (19)
"We live in FL and host a small family gathering for Thanksgiving every year. The house was perfect for us and received tons of compliments for location, size and amenities. Thanks for helping us make some wonderful memories!"
Amazing Waterfront Home on the Bush River

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!

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

9.8 out of 10, Exceptional, (8)
"David did a great job with everything! Everything I needed was available for me"
The price is AED 309
AED 525 total
includes taxes & fees
31 Dec - 1 January 2025
Clean Sanitized upscale suite. One or two beds. Private Bath

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

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

Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

10.0 out of 10, Exceptional, (14)
"Perfect house to rent! Clean, spacious, great neighborhood, beautiful property, & very dog friendly! My husband & I rent a different house in different states every year for our anniversary & never go to the same place twice; however, we may have to reconsider as this place was perfect & we may come back! The hot tub & deck(s) were relaxing, the location is great & very quiet, we had fun playing basketball, & we loved the dock and being able to watch the sun rise & set. We suffered the loss of a...
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

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!

Tip Of The Town Fresh and New 3 Bedroom Nest

9.8 out of 10, Exceptional, (8)
"We had a great stay at this property. Communication was seamless, the property was well taken care of, clean, and well decorated. "
The price is AED 588
AED 1,250 total
includes taxes & fees
29 Dec - 30 Dec
Tip Of The Town Fresh and New 3 Bedroom Nest

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

The Riverside Oasis waterfront with hot tub

10.0 out of 10, Exceptional, (4)
"We arrived to a cozy and warm home decorated beautifully for the holidays. Saturday we went for walks along the water and the kids did some biking. Dinner with our group was enjoyable at the large dining table where everyone had a seat- no need for a kiddy table in this house. Resting our heads down on luxurious bedding and waking up to beautiful water views was a delight. We can’t wait to come back with our clan."
The Riverside Oasis waterfront with hot tub

Cozy home with fenced in yard-Pet 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-Pet 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"
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.