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

Holiday Homes in Charlestown

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Our top choices for Charlestown holiday homes

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 €430
includes taxes & fees
19 Nov - 20 Nov
5-bedroom vacation home 5 minutes from historic Charlestown

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, (6 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.
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

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, (116 reviews)
"Host was very communicative."
United States
Lee Anne K.
Waterfront house with amazing views. Top of the Chesapeake

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

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 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
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.2 out of 10, Good, (20 reviews)
"Nice place"
United States
christine
The price is €77
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC

6. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.2 out of 10, Wonderful, (5 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.
Amish Countryside Escape at Forest Edge Farm

7. 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, (12 reviews)
"Excellent host, property, and experience. We enjoyed our stay, and we will be back."
United States
Kevin A.
The price is €121
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom bungalow in quaint Darlington with AC

8. 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, (7 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is €348
includes taxes & fees
15 Nov - 16 Nov
Bohemia Manor Farm

10. 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.
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

11. 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 €310
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

12. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
10.0 out of 10, Exceptional, (1 review)
"I was the first guest to stay at the Bohemia Hideaway and I was impressed. The place was spotless and brand new and beautifully decorated. The Owner left a care package filled with toiletries for personal use and every coffee flavor and tea flavor you could imagine. Even little honey packets. The scenery was beautiful. Tucked away and peaceful. Thank you for a wonderful stay."
United States
Isabelle M.
The price is €200
includes taxes & fees
26 Nov - 27 Nov
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

13. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
Elegant Family Stay • Quiet Neighborhood • Comfort

14. 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 €278
includes taxes & fees
13 Dec - 14 Dec
Watch Deer from a Farm Cottage

15. 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 €1,364
includes taxes & fees
16 Nov - 17 Nov
Waterfront Retreat w/ Hot Tub, Games & Views

16. 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 €221
includes taxes & fees
15 Nov - 16 Nov
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
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

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Charlestown Holiday Homes information

Number of reviews
392
Accommodation
119 Holiday Homes
Lowest Price
€77
Highest Price
€1,364