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

Charlestown Vacation 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 vacation rentals

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 SAR 933
SAR 1,936 total
includes taxes & fees
13 Oct - 14 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A riverside dock with boats, a covered seating area, and a bridge in the background.

2. 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 SAR 405
SAR 1,047 total
includes taxes & fees
15 Oct - 16 Oct
Historic Chesapeake City Stay
A wooden cabin with a porch, surrounded by dense forest.

3. 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 SAR 263
SAR 418 total
includes taxes & fees
2 Nov - 3 Nov
Country Get Away Studio Apartment
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

4. 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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is SAR 522
SAR 684 total
includes taxes & fees
19 Oct - 20 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

5. 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 SAR 642
SAR 734 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

6. 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)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is SAR 659
SAR 790 total
includes taxes & fees
11 Oct - 12 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

7. 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 SAR 676
SAR 1,258 total
includes taxes & fees
2 Nov - 3 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.

8. 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 SAR 267
SAR 363 total
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

9. 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 SAR 526
SAR 779 total
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom apartment in Lincoln University
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10. 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.
Sunset River Shack -amazing waterfront view
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 SAR 642
SAR 1,453 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 SAR 595
SAR 881 total
includes taxes & fees
12 Oct - 13 Oct
Winery & Vineyard Mill 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.

13. 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 SAR 458
SAR 798 total
includes taxes & fees
3 Nov - 4 Nov
Amish Countryside Escape at Forest Edge Farm
A bunk bed room with white bedding and blue throw blankets.

14. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is SAR 1,283
SAR 1,360 total
includes taxes & fees
25 Oct - 26 Oct
Bohemia Manor Farm
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

15. 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, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is SAR 469
SAR 577 total
includes taxes & fees
2 Nov - 3 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A covered deck area with a grill and outdoor seating.

16. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is SAR 710
SAR 877 total
includes taxes & fees
11 Oct - 12 Oct
Nature's Haven Tiny Home
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

17. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is SAR 653
SAR 804 total
includes taxes & fees
19 Oct - 20 Oct
Beachcomber Suite
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

18. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is SAR 628
SAR 1,428 total
includes taxes & fees
3 Nov - 4 Nov
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Terrace/patio

19. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is SAR 710
SAR 996 total
includes taxes & fees
11 Oct - 12 Oct
Tiny Home Tranquil Oasis
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

20. 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 SAR 939
SAR 1,116 total
includes taxes & fees
12 Oct - 13 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

8/10 Good
"Good alignment between price and quality. Staff was fantastic. The breakfast is not good. The rooms are dated (but very clean, quiet, and comfortable!)... and the pricing reflects that, so I would still rate this hotel quite highly and would stay here again."
Nathan W. 2-night trip
Posted 1 hour ago
Ramada by Wyndham Newark/Wilmington

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, you can find vacation rentals near popular sights in Charlestown, or you can select a more remote option if you're looking for a relaxing stay.

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

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home near Charlestown is located on a lake and has a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals will I find in Charlestown?

With 7 Expedia vacation rentals, you're sure 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 larger area, you’ll find Charlestown Town Hall and Hollywood Casino.

What are vacation rentals like in Charlestown?

Vacation rentals are private accommodations you can reserve for several days or more in Charlestown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.