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

Holiday Homes in Charlestown

  • 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$918
includes taxes & fees
29 Sept - 30 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

2. 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 NZ$343
includes taxes & fees
29 Sept - 30 Sept
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.

3. 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 NZ$177
includes taxes & fees
5 Oct - 6 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A kitchen with wooden cabinets, a microwave, a stove, and a coffee maker.

4. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is NZ$614
includes taxes & fees
1 Oct - 2 Oct
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
A bar area with a long counter, stools, and a dog.

5. 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, (23 reviews)
"Great rustic setting for a perfect weekend getaway!"
United States
Emily D.
The price is NZ$430
includes taxes & fees
29 Sept - 30 Sept
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

6. 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 NZ$393
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.

7. 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 NZ$637
includes taxes & fees
29 Sept - 30 Sept
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

8. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (14 reviews)
"This is our 3rd year in a row renting Jessica’s property. We truly enjoyed our stay. Highly recommend staying here. Beautiful backyard looking out to the bay! It has been a highlight staying here visiting for UD graduations. We hope to be back!"
United States
Natasha G.
The price is NZ$793
includes taxes & fees
4 Oct - 5 Oct
Sunset River Shack -amazing waterfront view
A bunk bed room with white bedding and blue throw blankets.

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$640
includes taxes & fees
11 Oct - 12 Oct
Bohemia Manor Farm
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, (7 reviews)
"I had such a great stay! Perfect spot for an individual or couple. Clean, quiet, and private. Would definitely recommend!"
United States
Tyler P.
The price is NZ$219
includes taxes & fees
29 Sept - 30 Sept
Restful Non-Shared Basement Suite In Harford MD
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

11. 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)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveller
The price is NZ$414
includes taxes & fees
29 Sept - 30 Sept
Winery & Vineyard Mill 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, (15 reviews)
"Everything was as advertised, clean, neat & spacious. Great communicators and readily available to answer questions."
United States
Gary S.
The price is NZ$2,789
includes taxes & fees
25 Oct - 26 Oct
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
A single-story white house with a red door, a front porch, and a brick pathway leading to the entrance.

13. 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 NZ$607
includes taxes & fees
7 Oct - 8 Oct
Watch Deer from a Farm Cottage
A two-story residential building with a stone facade, a large front lawn, and a driveway.

14. 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 NZ$617
includes taxes & fees
4 Oct - 5 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.

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 NZ$670
includes taxes & fees
1 Oct - 2 Oct
Abingdon Haven Hideaway
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)
"A must stay property"
United States
Rupesh D.
The price is NZ$2,753
includes taxes & fees
29 Sept - 30 Sept
Waterfront Retreat w/ Hot Tub, Games & Views
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent
"While the staff was awesome the rooms need help. There is paint peeling, locks not working properly and the ice machine on the first floor doesn’t work. However it’s somewhere cheap to sleep and if those small things don’t bother you then it’s perfect. Staff are always friendly and willing to help if you need it."
Stacy 1-night trip
Posted 9 hours ago
Baymont by Wyndham Newark at University of Delaware

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
324
Accommodation
117 Holiday Homes
Lowest Price
NZ$177
Highest Price
NZ$2,789