A river with a bridge, marina, and residential area.

Holiday Homes in Chesapeake City

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chesapeake City holiday homes

A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

1. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is AU$423
includes taxes & fees
18 Nov - 19 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A brick house with a front porch, a chimney, and a well-maintained lawn.

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$544
includes taxes & fees
25 Oct - 26 Oct
Bohemia Manor Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

3. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
The price is AU$536
includes taxes & fees
27 Oct - 28 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A two-story residential building with a stone facade, a large front lawn, and a driveway.

4. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is AU$492
includes taxes & fees
26 Oct - 27 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

5. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is AU$603
includes taxes & fees
27 Oct - 28 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

6. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$706
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

7. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is AU$752
includes taxes & fees
28 Oct - 29 Oct
Waterfront house with amazing views. Top of the Chesapeake
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

8. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.2 out of 10, Very good, (21 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is AU$546
includes taxes & fees
26 Oct - 27 Oct
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Exterior

9. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (3 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is AU$281
includes taxes & fees
26 Oct - 27 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

10. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is AU$138
includes taxes & fees
27 Oct - 28 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A living room with a large horse painting, two sofas, a coffee table, and a window with blinds.

11. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (30 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is AU$273
includes taxes & fees
25 Oct - 26 Oct
New Construction townhome close to everything downtown w/transparent pricing
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

12. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Elkton
10.0 out of 10, Exceptional, (17 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is AU$2,071
includes taxes & fees
30 Oct - 31 Oct
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

13. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is AU$331
includes taxes & fees
16 Nov - 17 Nov
Amish Countryside Escape at Forest Edge Farm
A house with a curved roof, a garden with various plants and flowers, and a red garage.

14. Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (11 reviews)
"Excellent host, property, and experience. We enjoyed our stay, and we will be back."
United States
Kevin A.
The price is AU$219
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom bungalow in quaint Darlington with AC
A living room with a fireplace, two sofas, a zebra rug, and a ceiling fan.

15. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.2 out of 10, Wonderful, (10 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
The price is AU$581
includes taxes & fees
26 Oct - 27 Oct
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
A storefront with a sign for 'Open Arts Antiques.'

16. Charming 3-bedroom, two-living room Victorian home in Historic New Castle

Charming 3-bedroom, two-living room Victorian home in Historic New Castle
Historical Old New Castle
The price is AU$773
includes taxes & fees
26 Oct - 27 Oct
Charming 3-bedroom, two-living room Victorian home in Historic New Castle
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

17. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is AU$530
includes taxes & fees
2 Nov - 3 Nov
Abingdon Haven Hideaway
A modern living room with a grey sofa, a round coffee table, and a large horse painting on the wall.

18. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful stay , comfortable and very warm welcoming"
United States
Shyaniece S.
The price is AU$343
includes taxes & fees
25 Oct - 26 Oct
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
A single-story house with a front porch, surrounded by a well-maintained lawn and trees.

19. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AU$490
includes taxes & fees
26 Oct - 27 Oct
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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.
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Top Chesapeake City Hotel Reviews

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

8/10 Good
"The room was clean. The air conditioner wasn't the greatest and one of the stairs was loose and almost killed me. But other than that it was fine. Breakfast was good!"
Denise 8-night trip
Posted 2 days ago
Sonesta ES Suites Wilmington - Newark

Find out more about Chesapeake City

Chesapeake City Holiday Homes information

Number of reviews
426
Accommodation
160 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$2,071