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
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 Charlestown holiday homes

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

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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is £367
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
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.

2. 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 £296
includes taxes & fees
26 Oct - 27 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A wooden deck with lounge chairs and a dock extending into calm water.

3. 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 £372
includes taxes & fees
28 Oct - 29 Oct
Waterfront house with amazing views. Top of the Chesapeake
Exterior

4. 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 £149
includes taxes & fees
7 Nov - 8 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.

5. 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 £72
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

6. 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 £224
includes taxes & fees
9 Nov - 10 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Living area

7. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is £251
includes taxes & fees
28 Oct - 29 Oct
Bohemia Manor Farm
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

8. 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 £160
includes taxes & fees
26 Oct - 27 Oct
Amish Countryside Escape at Forest Edge Farm
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

9. 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 £280
includes taxes & fees
27 Oct - 28 Oct
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.

10. 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 £116
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom bungalow in quaint Darlington with AC
A living room with a sofa, a television, and shelves with books and decorative items.

11. 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, (25 reviews)
"Great rustic setting for a perfect weekend getaway!"
United States
Emily D.
The price is £189
includes taxes & fees
26 Oct - 27 Oct
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
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 £1,097
includes taxes & fees
30 Oct - 31 Oct
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A two-story residential building with a stone facade, a large front lawn, and a driveway.

13. 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 £268
includes taxes & fees
26 Oct - 27 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
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.

14. 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 £289
includes taxes & fees
26 Oct - 27 Oct
Abingdon Haven Hideaway
A single-story white house with a front porch, a mailbox, and a number '715' on the door.

15. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
United States
Claudia L.
The price is £252
includes taxes & fees
11 Nov - 12 Nov
Watch Deer from a Farm Cottage
A wooden deck with a stone wall, a covered grill, and a view of a lake.

16. Waterfront Retreat w/ Hot Tub, Games & Views

Waterfront Retreat w/ Hot Tub, Games & Views
Whiteford
9.8 out of 10, Exceptional, (30 reviews)
"We like the property, it's location, and views.."
United States
Nazia M.
The price is £1,220
includes taxes & fees
26 Oct - 27 Oct
Waterfront Retreat w/ Hot Tub, Games & Views
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

17. 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, (29 reviews)
"What a great stay and a beautiful farm. We really enjoyed visiting the animals and hiking to the vinery."
United States
Anastasia T.
The price is £182
includes taxes & fees
8 Nov - 9 Nov
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
A bedroom with a bed, a dresser, a mirror, and a door.

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 £259
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 Charlestown Hotel Reviews

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

10/10 Excellent
"Nice place for low price safe lodging"
shawn 3-night trip
Posted 7 hours ago
Sonesta ES Suites Wilmington - Newark

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
427
Accommodation
119 Holiday Homes
Lowest Price
£72
Highest Price
£1,220