Chesapeake City Holiday Homes from €87: Search Top House Rentals

Chesapeake City Holiday Homes
Maryland
United States of America
Holiday Homes
Expedia.ie

Hotels in Chesapeake City Holiday Rentals in Chesapeake City Things to do in Chesapeake City Chesapeake City Car Hire Chesapeake City Holiday Packages

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chesapeake City holiday homes

A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

A residential backyard with a large tree, a small shed, and a view of a body of water.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and two bar stools.

A kitchen with wooden cabinets, a stainless steel refrigerator, a sink, and a dining area with a chair and table.

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)

9.4/10

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."

John

The price is €267

€267

includes taxes & fees

18 Nov - 19 Nov

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

A living room with a fireplace, sofa, coffee table, and a TV.

2. Bohemia Manor Farm

Bohemia Manor Farm

3.5 star property

Chesapeake City

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

The price is €344

€344

includes taxes & fees

27 Oct - 28 Oct

Bohemia Manor Farm

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

A compact kitchen with a black stove, white appliances, and dark cabinets.

A living room with a beige sofa, two armchairs, a glass coffee table, and a wall clock.

A dining area with a glass-top table surrounded by wicker chairs with patterned upholstery.

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)

9.8/10

Exceptional

(6 reviews)

"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"

Shana G.

The price is €333

€333

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.

A spacious living room with a sofa, a coffee table, and a fireplace. A kitchen is visible in the background.

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

4. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Beautiful well kept property with lots of room to relax."

Daniel J.

The price is €321

€321

includes taxes & fees

27 Oct - 28 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.

A beachside setting with two wicker lounge chairs, a round wooden table, and a beige umbrella.

A bathroom with a mirror, sink, and shower.

A waterfront property with multiple houses, a dock, and a beach.

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)

10/10

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."

Laura K.

The price is €354

€354

includes taxes & fees

27 Oct - 28 Oct

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

A wooden deck with lounge chairs and a dock extending into calm water.

A modern kitchen with granite countertops, a central island with bar seating, and pendant lighting.

A pier extending into calm water with a pebbled shore in the foreground.

A living room with a leather sofa, a television mounted on the wall, and a view of the outdoors through large sliding doors.

6. 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)

10/10

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"."

Joe M.

The price is €445

€445

includes taxes & fees

28 Oct - 29 Oct

Waterfront house with amazing views. Top of the Chesapeake

A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

A bathroom with a white sink, mirror, and two wall-mounted lights. There is a wooden door leading to a dining area with a table and chairs.

A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

A cozy living room with a dark-colored sofa, a wooden coffee table, and a dining table. There is a large window with a view of the outdoors, and a ceiling fan is visible.

7. 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)

9.8/10

Exceptional

(165 reviews)

"Family friendly, clean, quiet and great place to relax and watch the birds."

Teresa M.

The price is €439

€439

includes taxes & fees

27 Oct - 28 Oct

5-bedroom vacation home 5 minutes from historic Charlestown

A modern kitchen with dark cabinets, a white refrigerator, a microwave, an oven, and a bar area with stools.

A two-story house with a wooden deck and a staircase leading to the main entrance.

A laundry room with two front-loading washing machines, a utility sink, and a power outlet.

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)

8.2/10

Very good

(21 reviews)

"I’ve stayed in much better locations."

Grant H.

The price is €354

€354

includes taxes & fees

2 Nov - 3 Nov

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

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)

10/10

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!"

Don S.

The price is €178

€178

includes taxes & fees

6 Nov - 7 Nov

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.

A neatly made bed with a white comforter and pillows, a television on a stand, a patterned curtain, and a wall art piece.

A kitchen with white cabinets, a wooden island, and a washing machine.

A living room with a black sofa, patterned rug, and teal walls.

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)

7.6/10

Good

(19 reviews)

"Nice place"

christine

The price is €87

€87

includes taxes & fees

27 Oct - 28 Oct

Charming 2-bedroom house in Aberdeen with WiFi and AC

A dining table with a pumpkin centerpiece, a bench, and a window with blinds.

A living room with a black sofa, a round mirror, a dining table, and a kitchen area with a refrigerator.

A garden with a patio table and chairs, a red umbrella, and a brick pathway.

A kitchen with white cabinets, a stove, a sink, and a window with blinds.

11. Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Wilmington

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."

Chris D.

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

A dining area with a table and chairs, a chandelier, and a door.

A hallway with a wooden cabinet and a framed picture on the wall.

A gravel path in a park with trees and a distant building.

12. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

Nottingham

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

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. "

jckglss6 G.

Amish Countryside Escape at Forest Edge Farm

A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

A cozy cabin interior with a sectional sofa, a small table, and large windows offering a view of the forest.

A modern kitchen with white cabinetry, a central island, a built-in oven, and a stainless steel range hood.

A large house with a swimming pool, outdoor seating, and a fenced patio area.

13. 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)

10/10

Exceptional

(17 reviews)

"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."

Gary S.

The price is €1,313

€1,313

includes taxes & fees

30 Oct - 31 Oct

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

A house with a curved roof, a garden with various plants and flowers, and a red garage.

A narrow hallway leading to a bedroom with a bed, a wooden wardrobe, and a small table.

A well-maintained garden with various plants and a stone pathway leading to a building with a red exterior and a door labeled "Albert Squaree.20".

A rustic kitchen with wooden walls, a dining table with chairs, a hanging pendant light, and a refrigerator.

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)

10/10

Exceptional

(11 reviews)

"Excellent host, property, and experience. We enjoyed our stay, and we will be back."

Kevin A.

The price is €159

€159

includes taxes & fees

6 Nov - 7 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.

A room with a sofa, two armchairs, a dining table, and a chandelier.

A kitchen with white cabinets, a black countertop, a stove, and a refrigerator.

A living room with a blue sofa, two lamps, a painting, and potted plants.

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

9.4 out of 10, Exceptional, (11 reviews)

9.4/10

Exceptional

(11 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."

carla k.

The price is €372

€372

includes taxes & fees

2 Nov - 3 Nov

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

A brick building with a sign for 'The Mercury Cafe & Tea House' and a menu board.

A paved walkway along a rocky shoreline with trees and a flagpole.

A brick building with a sign for The Mercury Cafe & Tea House.

A brick building with a wine bar sign, a red door, and a window display of wine bottles.

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

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.

A residential house with a garage, a front porch, and a small garden area with mulch and shrubs.

A kitchen with a bar area, including a counter and three bar stools.

17. Abingdon Haven Hideaway

Abingdon Haven Hideaway

Abingdon

7.0 out of 10, Good, (2 reviews)

7.0/10

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."

Pam L.

The price is €344

€344

includes taxes & fees

27 Oct - 28 Oct

Abingdon Haven Hideaway

A wooden staircase leading to a beach with a clear view of the sea.

A bedroom with a bed, a dresser, a mirror, and a door.

A two-story house with a front porch, a pathway leading to the door, and a well-maintained lawn.

A modern kitchen with a dining area, a refrigerator, a coffee machine, and a window with blinds.

18. 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 €342

€342

includes taxes & fees

9 Nov - 10 Nov

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

A garden with a fountain, surrounded by lush greenery and flowering plants.

A flat-screen TV mounted on a wall displaying a yellow taxi on a city street. Below the TV, there is a fireplace with visible flames.

A large framed horse portrait on a wall above a beige sofa with patterned cushions.

A brick building with a paved walkway and a tree in front.

19. 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)

9.6/10

Exceptional

(30 reviews)

"We love this townhouse, close to everything!"

Judy P.

New Construction townhome close to everything downtown w/transparent pricing

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.

View all properties