Charlestown Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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 AU$610
includes taxes & fees
17 Nov - 18 Nov
Long Beach Cottage, (romantic couple’s getaway)
A bedroom with a bed, a nightstand, and a window overlooking a deck with outdoor furniture.

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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$685
includes taxes & fees
19 Nov - 20 Nov
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.

3. 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.
The price is AU$626
includes taxes & fees
17 Nov - 18 Nov
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A wooden deck with lounge chairs and a dock extending into calm water.

4. 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)
"Host was very communicative."
United States
Lee Anne K.
The price is AU$731
includes taxes & fees
11 Nov - 12 Nov
Waterfront house with amazing views. Top of the Chesapeake
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

5. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is AU$423
includes taxes & fees
23 Nov - 24 Nov
Historic Chesapeake City Stay
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

6. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is AU$150
includes taxes & fees
23 Nov - 24 Nov
Country Get Away Studio Apartment
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, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$321
includes taxes & fees
30 Nov - 1 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

8. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"The Port Deposit area is a favorite "mini-vacation" location with great bars/restaurants and beautiful walks. We've stayed at this property a number of times and we've found the rooms to be perfect for our needs. "
United States
Lance W.
The price is AU$448
includes taxes & fees
7 Dec - 8 Dec
Private 3 room Queen Suite w/Kitchenette
Exterior

9. 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 AU$283
includes taxes & fees
18 Nov - 19 Nov
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A living room with a white sofa, a clock, a dining area with a table and chairs, and a kitchen in the background.

10. 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, (15 reviews)
"It is in a lovely neighborhood and the hosts were very welcoming of us and my 2 dogs. We were all very comfortable."
United States
Barb
The price is AU$253
includes taxes & fees
23 Nov - 24 Nov
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

11. 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, (60 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is AU$326
includes taxes & fees
7 Dec - 8 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

12. 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
The price is AU$465
includes taxes & fees
11 Nov - 12 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
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.

13. 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 AU$123
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

14. 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.
The price is AU$300
includes taxes & fees
16 Nov - 17 Nov
Amish Countryside Escape at Forest Edge Farm
A house with a curved roof, a garden with various plants and flowers, and a red garage.

15. 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 AU$206
includes taxes & fees
11 Nov - 12 Nov
Cozy 1-bedroom bungalow in quaint Darlington with AC
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

16. 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 AU$264
includes taxes & fees
11 Nov - 12 Nov
Cozy 1-bedroom apartment in Lincoln University
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

17. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is AU$212
includes taxes & fees
9 Dec - 10 Dec
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

18. 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 AU$341
includes taxes & fees
16 Nov - 17 Nov
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

19. 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.
The price is AU$539
includes taxes & fees
17 Nov - 18 Nov
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A two-story house with a deck, a barbecue grill, and a covered patio area.

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

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (25 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is AU$712
includes taxes & fees
23 Nov - 24 Nov
Thunder Hill Retreat - Spacious/Deck/Hot tub
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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Find holiday rentals that suit your style

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Top Charlestown Hotel Reviews

A lobby with seating, a reception desk, and a cityscape mural on the wall.
La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton
Elkton

8/10 Good

Overall the place is fine. Just limited in services.
Australia
peter
Reviewed September 7, 2023
La Quinta Inn & Suites by Wyndham Newark - Elkton

Find out more about Charlestown

Everything you need to know about Charlestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charlestown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Charlestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlestown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlestown holiday rentals we have selected for you start as low as AU$123 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Charlestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charlestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charlestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.