Holiday 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

Featured Holiday Homes in Chesapeake City

1 bedroom, WiFi, bed sheets
Oaxaca, a private room with private entrance
9.0 out of 10, Wonderful, (8)
"Ms Laura is such a great hostess. The room is so comfy and clean. We hope to stay again.. :)"
The price is AU$177
includes taxes & fees
27 May - 28 May
Oaxaca, a private room with private entrance
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Save an average of 15% on thousands of hotels when you're signed in
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (85)
"Such a comfortable place to stay! Fully stocked kitchen, big rooms with comfortable beds and linens. Everything is clean and the appliances are new. Sweet welcome gift of pastries and water. Quiet neighborhood. Easy to access and property host was very responsive."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (7)
"Way to make us feel welcome. From the accommodations to the amenities this property is a vrbo treasure. The owners exceeded our expectations in every way."
Historic home in the heart of Main Street- walkable to shops and restaurants
Fridge, microwave, oven, stovetop
Newly Renovated 4 bedroom home W/big yard and driveway
2.0 out of 10, (1)
"We pulled up to the neighborhood in the early evening and oh my it was not a safe place. We stayed the first night with few options to leave so late. The kitchen sink hot water was not hot and the dishes were not clean in the cabinets. We witnessed illicit activity on the street outside. Also there was people screaming and shining lights in windows all night. We obviously did not feel safe to stay and left terrified in the morning. Not a place to stay with children or if you value your vehicle...
Newly Renovated 4 bedroom home W/big yard and driveway
Fridge, microwave, stovetop, cookware/dishes/utensils
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking
Smart TV, fireplace
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
The price is AU$501
includes taxes & fees
23 June - 24 June
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
Fridge, microwave, oven, stovetop
Water-view cabin on 13 acres with private hot tub & kayaks - dog-friendly
8.0 out of 10, Very good, (1)
"A little hard to find but once you do a comfortable stay with gorgeous sunrises awaits you. Plenty of room and a wonderful kitchen."
Water-view cabin on 13 acres with private hot tub & kayaks - dog-friendly
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Property grounds
Spacious North East Home w/ Fenced Yard & Fire Pit
Spacious North East Home w/ Fenced Yard & Fire Pit
Property grounds
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (42)
"Suzanne's place was very comfortable and she supplied everything you'd need. It was fun cooking in her kitchen and I was also able to work remotely as well."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Property grounds
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (19)
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Pool
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, (154)
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Private kitchen
Charming Rustic Retreat
10.0 out of 10, Exceptional, (1)
"We were a group of eight, up for a birthday party. We all had a great time! Everyone was impressed with the place and location. The two separate living areas worked well with our group. We especially enjoyed the chalkboard and pool table. We loved every minute of our stay. Jeff is a great host, with great communication. This was a great find! We will definitely look to stay again in the future."
Charming Rustic Retreat
Fridge, microwave, oven, stovetop
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
8.0 out of 10, Very good, (6)
"Beautiful house! Large house with plenty of room for everyone! Great deck and basement area. Property Manager was accomodating and professional. Would definitely stay again!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Fridge, microwave, oven, stovetop
Beautiful Brick-Wall House in Historic Newcastle
7.6 out of 10, Good, (5)
"This is an older home that has had some upgrades and an addition made by non-professionals. They could use a new bathtub. It’s rough around the edges but an okay place to and sleep. The manager was nice to work with and answered our questions."
Beautiful Brick-Wall House in Historic Newcastle
Beach
Riverfront Country House on The Sassafras River
10.0 out of 10, Exceptional, (12)
"My family had a relaxing, fun weekend at the house. My 20-something children all loved the window seat where they curled up and read. We enjoyed time on the river with the kayaks and paddleboards. The beds were comfy, kitchen well stocked and overall the house is cozy. It was the perfect get-away for our family!"
Riverfront Country House on The Sassafras River
Fridge, microwave, oven, stovetop
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
Don't see what you're looking for?
See all available properties in Chesapeake City
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.

Other property types in Chesapeake City

Pool
Historic Chesapeake City Stay
8.0 out of 10, Very good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is AU$362
includes taxes & fees
27 May - 28 May
Historic Chesapeake City Stay
Property grounds
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, (2)
"Two of my brothers and an old friend came down to the c&d canal trail for a long weekend and a lot of bicycle riding. This house was right on the trail. A great house with great views. We were also within walking distance of a very good seafood restaurant. It was a perfect weekend. As far as the house it had everything we needed. We wanted for nothing. When we arrived at the house there was chocolates and snacks waiting for us as well as beers and sodas in the fridge with a note to help...
Chesapeake City Overlook: Breathtaking View!
Smart TV
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
9.6 out of 10, Exceptional, (5)
"Our group of 15 gathered here for a long weekend in July to attend a family event in the area. The house was WONDERFUL, STYLISH & SPACIOUS. And Chesapeake City itself was a surprise bonus… several gift shops, a cute ice cream shop, coffee & breakfast cafe, dinner restaurants - all within walking distance! Loved: everything about the house… proximity to the quaint town… plenty of hot water… awesome AC upstairs…Brad the owner answered emails very quickly… *minor* issues: the main floor AC...
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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.

Chesapeake City Holiday Homes information

Number of reviews
431
Accommodation
110 Holiday Homes
Lowest Price
AU$177
Highest Price
AU$501

Recent Reviews in Chesapeake City
Expedia verified reviews