Search Vacation Homes in Chesapeake City

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Compare 130 Vacation Homes in Chesapeake City with updated reviews, rates, and availability.

Pool | Outdoor 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
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
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
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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
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!"
The price is $500
$603 total
includes taxes & fees
May 23 - May 24
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
Fridge, microwave, oven, coffee/tea maker
Tranquil Haven: Modern Retreat in Newark
10.0 out of 10, Exceptional, (4)
"Good overall, communication was great and property owner allowed us to check out a little later to help us out."
Tranquil Haven: Modern Retreat in Newark
On the beach, sun loungers, beach towels
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (89)
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
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.
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.
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
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (34)
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
View from property
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (126)
"This house setting was a little slice of paradise. We saw a beaver swimming, blue herons, eagles, ducks in the water and yard. Would definitely come back again."
The price is $359
$653 total
includes taxes & fees
May 27 - May 28
Top of the Chesapeake - Minutes from Historic Charlestown
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!
Pool | Outdoor pool, a heated 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.
Beach nearby, sun loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, (26)
"This was our second stay here. The property is well appointed for a relaxing stay with 5-star views! Lots of room for family to spread out and relax, and the kitchen has everything you need to make delicious meals. Betterton is extra relaxing with its beautiful views and quiet stillness. We'll be back!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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 $75
$115 total
includes taxes & fees
May 27 - May 28
Oaxaca, a private room with private entrance
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
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..
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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

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!
Exterior
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!!!
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 $75
$115 total
includes taxes & fees
May 27 - May 28
Oaxaca, a private room with private entrance
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 Vacation Homes information

Number of reviews
431
Accommodation
130 Vacation Homes
Lowest Price
$75
Highest Price
$500

Recent reviews of Chesapeake City hotels
Expedia verified reviews