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

Charlestown Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Charlestown vacation rentals

Marina

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 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.
$263 nightly
The price is $279
Sep 23 - Sep 24
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

2. 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.
$152 nightly
The price is $161
Sep 22 - Sep 23
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Sun loungers, beach towels

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.
$490 nightly
The price is $520
Sep 29 - Sep 30
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Sep 28 - Sep 29
Total with taxes and fees
Country Get Away Studio Apartment
Coffee/tea maker, fridge, microwave, oven

5. 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.
$203 nightly
The price is $215
Sep 24 - Sep 25
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior

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, (53 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
$200 nightly
The price is $211
Sep 22 - Sep 23
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Interior

7. 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.
$273 nightly
The price is $289
Sep 22 - Sep 23
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette

8. 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.
$195 nightly
The price is $196
Sep 27 - Sep 28
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
TV

9. 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
$102 nightly
The price is $108
Sep 29 - Sep 30
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

10. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
$335 nightly
The price is $355
Sep 23 - Sep 24
Total with taxes and fees
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Coffee/tea maker, fridge, microwave, oven

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)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$358 nightly
The price is $380
Sep 23 - Sep 24
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Outdoor dining

12. 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.
$199 nightly
The price is $200
Sep 23 - Sep 24
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Bar (on property)

13. 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, (22 reviews)
"Great rustic setting for a perfect weekend getaway!"
United States
Emily D.
$220 nightly
The price is $243
Sep 24 - Sep 25
Total with taxes and fees
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Coffee/tea maker, fridge, microwave, oven

14. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (1 review)
$171 nightly
The price is $189
Sep 22 - Sep 23
Total with taxes and fees
Cozy 1-bedroom apartment in Lincoln University
Terrace/patio

15. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
9.8 out of 10, Exceptional, (7 reviews)
"I had such a great stay! Perfect spot for an individual or couple. Clean, quiet, and private. Would definitely recommend!"
United States
Tyler P.
$119 nightly
The price is $126
Oct 5 - Oct 6
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
Exterior

16. 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.
$448 nightly
The price is $495
Sep 24 - Sep 25
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Terrace/patio

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (8 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
$175 nightly
The price is $186
Sep 23 - Sep 24
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Terrace/patio

18. 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
$225 nightly
The price is $234
Sep 22 - Sep 23
Total with taxes and fees
Nature's Haven Tiny Home
Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

19. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$396 nightly
The price is $420
Oct 5 - Oct 6
Total with taxes and fees
Bohemia Manor Farm
Terrace/patio

20. 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.
$233 nightly
The price is $242
Sep 22 - Sep 23
Total with taxes and fees
Tiny Home Tranquil Oasis
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

La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton

10/10 Excellent
"Très grande chambre avec espace bureau séparé. Fût très pratique pour nous."
marc 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Newark - Elkton

Find out more about Charlestown

Everything you need to know about Charlestown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Charlestown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Charlestown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown vacation 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 vacation.

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 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 8 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.