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

Charlestown Vacation Rentals

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Our top choices for Charlestown vacation rentals

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 CA $399
CA $615 total
includes taxes & fees
Nov 17 - Nov 18
Long Beach Cottage, (romantic couple’s getaway)

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 CA $315
CA $692 total
includes taxes & fees
Nov 19 - Nov 20
5-bedroom vacation home 5 minutes from historic Charlestown

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 CA $363
CA $590 total
includes taxes & fees
Nov 19 - Nov 20
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

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, (116 reviews)
"Host was very communicative."
United States
Lee Anne K.
The price is CA $375
CA $732 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront house with amazing views. Top of the Chesapeake

5. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (54 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is CA $100
CA $147 total
includes taxes & fees
Nov 24 - Nov 25
Country Get Away Studio Apartment

6. 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 CA $193
CA $428 total
includes taxes & fees
Nov 15 - Nov 16
Historic Chesapeake City Stay

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 CA $211
CA $302 total
includes taxes & fees
Nov 22 - Nov 23
Quarry Landing - Center of Town & River View - 3 Bedroom

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 CA $250
CA $431 total
includes taxes & fees
Nov 16 - Nov 17
Private 3 room Queen Suite w/Kitchenette

9. 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 CA $198
CA $246 total
includes taxes & fees
Nov 15 - Nov 16
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

10. 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 CA $278
CA $305 total
includes taxes & fees
Nov 16 - Nov 17
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.2 out of 10, Good, (20 reviews)
"Nice place"
United States
christine
The price is CA $96
CA $120 total
includes taxes & fees
Nov 18 - Nov 19
Charming 2-bedroom house in Aberdeen with WiFi and AC

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 CA $231
CA $431 total
includes taxes & fees
Nov 19 - Nov 20
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

13. 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 CA $177
CA $280 total
includes taxes & fees
Nov 19 - Nov 20
Amish Countryside Escape at Forest Edge Farm

14. 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 CA $171
CA $200 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom bungalow in quaint Darlington with AC

15. 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 CA $182
CA $262 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom apartment in Lincoln University

16. 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 CA $178
CA $197 total
includes taxes & fees
Nov 16 - Nov 17
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

17. 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 CA $236
CA $320 total
includes taxes & fees
Nov 19 - Nov 20
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

18. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $498
CA $528 total
includes taxes & fees
Nov 19 - Nov 20
Bohemia Manor Farm

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 CA $218
CA $497 total
includes taxes & fees
Nov 16 - Nov 17
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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, (18 reviews)
"Absolutely amazing stay. Host is extremely responsive and the property is incredible. Highly recommend!!"
United States
Erika R.
The price is CA $1,239
CA $2,049 total
includes taxes & fees
Nov 15 - Nov 16
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Charlestown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.