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

Charlestown Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Charlestown holiday rentals

A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

1. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is HK$2,882
HK$4,364 total
includes taxes & fees
22 Oct - 23 Oct
Long Beach Cottage, (romantic couple’s getaway)
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 HK$2,209
HK$3,645 total
includes taxes & fees
18 Oct - 19 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

3. 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 HK$1,949
HK$4,046 total
includes taxes & fees
13 Oct - 14 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

4. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (57 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is HK$1,377
HK$1,660 total
includes taxes & fees
12 Oct - 13 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

5. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$1,091
HK$1,431 total
includes taxes & fees
12 Oct - 13 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Private kitchen

6. 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 HK$1,342
HK$1,533 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A kitchen with white cabinets, a wooden countertop, a built-in oven, and a window.

7. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (17 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,161
HK$1,813 total
includes taxes & fees
9 Nov - 10 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom
A riverside dock with boats, a covered seating area, and a bridge in the background.

8. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is HK$848
HK$2,188 total
includes taxes & fees
15 Oct - 16 Oct
Historic Chesapeake City Stay
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

9. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"This is a very nice apt. The owner was very receptive to any questions we had, even allowed an early checkin."
United States
Kathleen B.
The price is HK$1,373
HK$2,595 total
includes taxes & fees
13 Oct - 14 Oct
Private 3 room Queen Suite w/Kitchenette
A bathroom with wooden cabinets, a white sink, and a large mirror.

10. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (50 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is HK$549
HK$873 total
includes taxes & fees
22 Oct - 23 Oct
Country Get Away Studio Apartment
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

11. 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 HK$1,342
HK$3,036 total
includes taxes & fees
20 Oct - 21 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

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, (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 HK$1,243
HK$1,841 total
includes taxes & fees
12 Oct - 13 Oct
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

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

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.2 out of 10, Wonderful, (5 reviews)
The price is HK$1,130
HK$2,313 total
includes taxes & fees
1 Nov - 2 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

14. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (2 reviews)
"My girlfriend and I were in town for a wedding and the VRBO was perfect. Great privacy, lovely decor, and comfortable bed. A full use kitchen was great to have. Cheech (the pig!!) was so friendly and the host even dropped off carrots for us to feed him. The host responded to every question in a timely manner and check in and check out were painless."
United States
Zachary Z.
The price is HK$989
HK$1,490 total
includes taxes & fees
12 Oct - 13 Oct
Cozy 1-bedroom apartment in Lincoln University
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

15. 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 HK$910
HK$1,612 total
includes taxes & fees
9 Nov - 10 Nov
Amish Countryside Escape at Forest Edge Farm
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

16. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (6 reviews)
"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...
United States
Karen
The price is HK$1,962
HK$2,333 total
includes taxes & fees
16 Oct - 17 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A two-story house with a deck, a barbecue grill, and a covered patio area.

17. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is HK$1,942
HK$4,183 total
includes taxes & fees
19 Oct - 20 Oct
Thunder Hill Retreat - Spacious/Deck/Hot tub
A bunk bed room with white bedding and blue throw blankets.

18. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,854
HK$3,025 total
includes taxes & fees
25 Oct - 26 Oct
Bohemia Manor Farm
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.

19. 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 HK$558
HK$758 total
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A spacious living area with a large gray sofa, a coffee table, and a bar area with stools.

20. 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 HK$6,817
HK$11,913 total
includes taxes & fees
25 Oct - 26 Oct
Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court
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

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Can I find a holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Charlestown has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals will I find in Charlestown?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Charlestown stay.

What can I see and do in Charlestown?

While exploring the area, visit family-friendly sights like Plumpton Park Zoo, or get outside and enjoy nature at North East Beach Area. In the wider area, you’ll find Charlestown Town Hall and Hollywood Casino.

What are holiday rentals like in Charlestown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Charlestown. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.