A marina with boats docked, a river, and a row of houses along the riverbank.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Charlestown holiday homes

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

1. 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, (157 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is £427
includes taxes & fees
16 Sept - 17 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
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.

2. 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 £77
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC

3. 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, (2 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 £143
includes taxes & fees
24 Aug - 25 Aug
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

4. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
8.8 out of 10, Excellent, (3 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 £170
includes taxes & fees
24 Aug - 25 Aug
Amish Countryside Escape at Forest Edge Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

5. 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)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is £268
includes taxes & fees
1 Sept - 2 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A house with a curved roof, a garden with various plants and flowers, and a red garage.

6. 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)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
The price is £126
includes taxes & fees
25 Aug - 26 Aug
Cozy 1-bedroom bungalow in quaint Darlington with AC
A hotel room with two beds, a small table with a vase of flowers, a chair, and a view of the outside through a window with curtains.

7. Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is £159
includes taxes & fees
22 Aug - 23 Aug
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
A brick house with a front porch, a chimney, and a well-maintained lawn.

8. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is £262
includes taxes & fees
25 Aug - 26 Aug
Bohemia Manor Farm
A bar area with a long counter, stools, and a dog.

9. Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (21 reviews)
"Laura was very welcoming and we loved the loft! Such a charming place for a quiet get away!"
United States
Dominic L.
The price is £182
includes taxes & fees
31 Aug - 1 Sept
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
A covered patio area with stone flooring, wooden beams, and a fire pit.

10. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
9.8 out of 10, Exceptional, (6 reviews)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is £85
includes taxes & fees
2 Sept - 3 Sept
Restful Non-Shared Basement Suite In Harford MD
A dining area with a rectangular table, red chairs, and hanging pendant lights.

11. Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is £239
includes taxes & fees
24 Aug - 25 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
A single-story white house with a front porch, a mailbox, and a number 715 sign.

12. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (6 reviews)
"Pet friendly."
United States
Claudia L.
The price is £245
includes taxes & fees
30 Aug - 31 Aug
Watch Deer from a Farm Cottage
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

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, (14 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is £1,148
includes taxes & fees
8 Sept - 9 Sept
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

14. Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (27 reviews)
"Beautiful, rustic apartment on a farm was the perfect relaxing environment we needed for the weekend. Loved walking around the wooded grounds and meeting the farm animals. The apartment itself was spacious, clean, and comfortable. Will definitely try to cone back. "
United States
Jeff J.
The price is £178
includes taxes & fees
26 Aug - 27 Aug
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
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.

15. 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 £280
includes taxes & fees
28 Aug - 29 Aug
Abingdon Haven Hideaway
A two-story residential building with a stone facade, a large front lawn, and a driveway.

16. 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 £282
includes taxes & fees
31 Aug - 1 Sept
Elegant Family Stay • Quiet Neighborhood • Comfort
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 Charlestown Hotel Reviews

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"The hotel was clean. They were having new carpet installed in the hallways while we were there. But it didn't take away from our stay at all. The beds are really comfortable. The breakfast was good. The staff was very nice. I stay at this location frequently and have always had a good experience."
Adrian 2-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
307
Accommodation
115 Holiday Homes
Lowest Price
£77
Highest Price
£1,148