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

Our top choices for Charlestown vacation rentals

A wooden deck with wicker lounge chairs and a white sofa, overlooking a body of water.

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)
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

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 $344
CA $728 total
includes taxes & fees
Nov 19 - Nov 20
5-bedroom vacation home 5 minutes from historic Charlestown
A beachside seating area with wicker chairs, a striped cushion, a wooden table, and a beach umbrella.

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
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, (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
A wooden deck with a glass-top table and metal chairs.

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
A riverside dock with boats, a covered seating area, and a bridge in the background.

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 $408 total
includes taxes & fees
Nov 16 - Nov 17
Historic Chesapeake City Stay
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 CA $211
CA $302 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $250
CA $431 total
includes taxes & fees
Nov 16 - Nov 17
Private 3 room Queen Suite w/Kitchenette
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

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 $248 total
includes taxes & fees
Nov 22 - Nov 23
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.

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.
A kitchen with white cabinets, a wooden island, and a washing machine.

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 $116
CA $141 total
includes taxes & fees
Dec 1 - Dec 2
Charming 2-bedroom house in Aberdeen with WiFi and AC
A wooden deck with two cushioned chairs, a view of a lake, and a small shed in the background.

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
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
9.2 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 $167
CA $270 total
includes taxes & fees
Nov 19 - Nov 20
Amish Countryside Escape at Forest Edge Farm
A house with a curved roof, a garden with various plants and flowers, and a red garage.

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
A pig in a fenced area with a house and trees in the background.

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 $180
CA $259 total
includes taxes & fees
Nov 16 - Nov 17
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.

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
A rustic dining area with a wooden table and chairs, a patterned rug, and exposed wooden beams.

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 $335 total
includes taxes & fees
Nov 22 - Nov 23
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Beach bar

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 $508
CA $539 total
includes taxes & fees
Nov 17 - Nov 18
Bohemia Manor Farm
A compact kitchen with black cabinets, stainless steel appliances, and a patterned rug.

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 $498 total
includes taxes & fees
Nov 16 - Nov 17
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A swimming pool with a slide, lounge chairs, and a gazebo.

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 $1,240
CA $2,050 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

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent
"It was clean and comfortable."
Todd 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Newark - Wilmington

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, 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 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlestown vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlestown vacation rentals we have selected for you start as low as CA $147 per night. Entering your travel dates in the search wizard 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 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.