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

Tip Of The Town Fresh and New 3 Bedroom Nest
9.8 out of 10, Exceptional, (7)
"Loved the convenience to the town of South East and Blue Elk Vineyard. The property was very clean. Having an EV charger was so helpful."
The price is AED 624
AED 1,293 total
includes taxes & fees
24 Nov - 25 Nov
Tip Of The Town Fresh and New 3 Bedroom Nest
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (100)
"Great stay - we were hardly there but the convenience of the location was great and everything was just as described. Thank you!"
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Sweet Little Home Away From Home, North East, MD
10.0 out of 10, Exceptional, (4)
"My family enjoyed our stay at Angela's house in North East. The house was clean, beds were comfortable, kitchen had what we needed. We'd stay there again."
Sweet Little Home Away From Home, North East, MD
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!
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
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
8.6 out of 10, Excellent, (10)
"The house had plenty of space and location was great!"
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Sunset River Cottage encapsulates nautical romance.
9.0 out of 10, Wonderful, (12)
"This property is gorgeous! It was everything I could have hoped for. I was in town for a wedding in Earleville in search of a dog friendly rental. I am so happy I found this place. The cottage is down the long driveway neighboring other cottages/houses. Very cute fenced in entryway. The check-in process was very easy with the door code for entry. The cottage was super cute, plenty of space. The pups and I spent most of our time outside enjoying the view. The yard overlooking the water has a...
Sunset River Cottage encapsulates nautical romance.
Ultimate Retreat @ Papermill Rd
8.8 out of 10, Excellent, (5)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
Home Away from Home - Local Shops, Restaurants & Grocery stores within 4 miles!
9.6 out of 10, Exceptional, (4)
"Great place, Great host ! Will definitely stay here again. Highly recommended."
The price is AED 624
AED 1,121 total
includes taxes & fees
24 Nov - 25 Nov
Home Away from Home - Local Shops, Restaurants & Grocery stores within 4 miles!
Luxurious and spacious townhome with all necessary amenities awaits your stay.
10.0 out of 10, Exceptional, (3)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your 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, (1)
"We had a great time staying here. The inside is so cute and comfortable. Location is great and the host is very quick to respond and accommodate requests. 10/10 "
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AED 1,319
AED 2,379 total
includes taxes & fees
25 Nov - 26 Nov
Top of the Chesapeake - Minutes from Historic Charlestown
Beautiful Colonial Style Home in Nottingham PA
9.8 out of 10, Exceptional, (6)
"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."
Beautiful Colonial Style Home in Nottingham PA
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
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
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

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AED 1,102
AED 1,881 total
includes taxes & fees
25 Nov - 26 Nov
Historic Chesapeake City Stay
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
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.