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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Charlestown vacation rentals

Exterior

1. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (45 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
$105 nightly
The price is $111
Aug 10 - Aug 11
Total with taxes and fees
Country Get Away Studio Apartment
Marina

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 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.
$265 nightly
The price is $281
Aug 9 - Aug 10
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

3. 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, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Aug 8 - Aug 9
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
TV

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
$89 nightly
The price is $95
Aug 17 - Aug 18
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
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, (2 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.
$186 nightly
The price is $187
Aug 3 - Aug 4
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Interior

6. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"Perfect location for that town. "
United States
Hisham M.
$271 nightly
The price is $287
Aug 3 - Aug 4
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Exterior

7. 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, (50 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
$199 nightly
The price is $210
Aug 3 - Aug 4
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Sun loungers, beach towels

8. 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, (155 reviews)
"Kitchen was fully equipped for a large family, beautiful views and perfect family getaway! "
United States
Kshama C.
$556 nightly
The price is $589
Sep 1 - Sep 2
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Coffee/tea maker, fridge, microwave, oven

9. 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
9.6 out of 10, Exceptional, (5 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$331 nightly
The price is $351
Aug 17 - Aug 18
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Outdoor dining

10. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 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.
$220 nightly
The price is $221
Aug 24 - Aug 25
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Smart TV

11. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
$255 nightly
The price is $270
Aug 24 - Aug 25
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Coffee/tea maker, fridge, microwave, oven

12. 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, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$289 nightly
The price is $306
Aug 17 - Aug 18
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
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, (21 reviews)
"Laura was very welcoming and we loved the loft! Such a charming place for a quiet get away!"
United States
Dominic L.
$219 nightly
The price is $242
Aug 6 - Aug 7
Total with taxes and fees
Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses
Terrace/patio

14. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (4 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.
$112 nightly
The price is $119
Aug 18 - Aug 19
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
Terrace/patio

15. 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, (3 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.
$634 nightly
The price is $666
Aug 23 - Aug 24
Total with taxes and fees
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Exterior

16. 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, (9 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
$164 nightly
The price is $174
Aug 24 - Aug 25
Total with taxes and fees
Cozy 1-bedroom bungalow in quaint Darlington with AC
Property grounds

17. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (7 reviews)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
$421 nightly
The price is $446
Aug 3 - Aug 4
Total with taxes and fees
Sunset River Shack -amazing waterfront view
1 bedroom, iron/ironing board, WiFi (free), bed sheets

18. Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$188 nightly
The price is $200
Aug 4 - Aug 5
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Smart TV

19. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
$150 nightly
The price is $166
Aug 10 - Aug 11
Total with taxes and fees
Cozy 1-bedroom apartment in Lincoln University
Property grounds

20. 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.
$167 nightly
The price is $181
Aug 10 - Aug 11
Total with taxes and fees
Beachcomber Suite
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

Hampton Inn & Suites Wilmington Christiana

Hampton Inn & Suites Wilmington Christiana

8/10 Good
"Room was nicely appointed and clean. Front desk staff seemed ok. Cleaning staff seemed less pleasant."
David 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Wilmington Christiana

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 $187 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?

Sunset River Cottage: This vacation home rental near Charlestown is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Fred Rust Ice Arena, or get outside and enjoy nature at North East Beach Area. In the larger area, you’ll find Charlestown Town Hall and Upper Bay Museum.

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.