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

Holiday Homes in Charlestown

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Charlestown holiday homes

Exterior

1. 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 €168
includes taxes & fees
12 Aug - 13 Aug
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Sun-loungers, beach towels

2. 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, (156 reviews)
"Kitchen was fully equipped for a large family, beautiful views and perfect family getaway! "
United States
Kshama C.
The price is €555
includes taxes & fees
8 Sept - 9 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
TV

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is €92
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house in Aberdeen with WiFi and AC
Coffee/tea maker, fridge, microwave, oven

4. 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
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is €316
includes taxes & fees
25 Aug - 26 Aug
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Bar (on property)

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, (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 €214
includes taxes & fees
24 Aug - 25 Aug
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Outdoor dining

6. 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 €197
includes taxes & fees
24 Aug - 25 Aug
Amish Countryside Escape at Forest Edge Farm
Terrace/patio

7. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (5 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 €126
includes taxes & fees
25 Aug - 26 Aug
Restful Non-Shared Basement Suite In Harford MD
Exterior

8. 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, (10 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 €166
includes taxes & fees
25 Aug - 26 Aug
Cozy 1-bedroom bungalow in quaint Darlington with AC
Dining

9. 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 €282
includes taxes & fees
24 Aug - 25 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

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

11. 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 €285
includes taxes & fees
30 Aug - 31 Aug
Watch Deer from a Farm Cottage
Interior

12. 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 €203
includes taxes & fees
24 Aug - 25 Aug
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Smart TV, fireplace, table football, ping pong

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 €1,356
includes taxes & fees
8 Sept - 9 Sept
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
Exterior

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 €318
includes taxes & fees
12 Aug - 13 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort
Interior

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 €346
includes taxes & fees
27 Aug - 28 Aug
Abingdon Haven Hideaway
Property grounds

16. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.4 out of 10, Exceptional, (10 reviews)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
Sunset River Shack -amazing waterfront view
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

Red Roof Inn Perryville

Red Roof Inn Perryville

10/10 Excellent
"We will definitely plan to stay here again if we drive around here. Rooms renovated and very well equipped. Like an idea of "Quiet Hours"."
Krzysztof 1-night trip
Posted 2 hours ago
Red Roof Inn Perryville

Find out more about Charlestown

Charlestown Holiday Homes information

Number of reviews
312
Accommodation
115 Holiday Homes
Lowest Price
€92
Highest Price
€1,356