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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Charlestown vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥17,561
￥45,330 total
includes taxes & fees
Jul 2 - Jul 3
Historic Chesapeake City Stay
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
The price is ￥10,930
￥15,019 total
includes taxes & fees
Jul 6 - Jul 7
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is ￥11,335
￥18,023 total
includes taxes & fees
Jul 7 - Jul 8
Country Get Away Studio Apartment
Exterior

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, (1 review)
"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 ￥26,476
￥30,081 total
includes taxes & fees
Jul 2 - Jul 3
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Exterior

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.
The price is ￥19,432
￥26,091 total
includes taxes & fees
Jul 9 - Jul 10
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

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, (47 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is ￥28,419
￥34,244 total
includes taxes & fees
Jul 9 - Jul 10
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio

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.
The price is ￥8,943
￥18,097 total
includes taxes & fees
Jul 13 - Jul 14
Restful Non-Shared Basement Suite In Harford MD
Terrace/patio

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 ￥30,605
￥37,813 total
includes taxes & fees
Jul 2 - Jul 3
Nature's Haven Tiny Home
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (23 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is ￥42,014
￥86,575 total
includes taxes & fees
Jul 2 - Jul 3
Thunder Hill Retreat - Spacious/Deck/Hot tub
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (7 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is ￥16,081
￥29,456 total
includes taxes & fees
Jul 2 - Jul 3
Summer Rustic Camping with AC and King Bed
Exterior

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, (3 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.
The price is ￥19,917
￥24,545 total
includes taxes & fees
Jul 20 - Jul 21
Cozy 1-bedroom bungalow in quaint Darlington with AC
Dining

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (23 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is ￥31,333
￥53,632 total
includes taxes & fees
Jul 8 - Jul 9
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Fridge, microwave, oven, stovetop

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
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥21,861
￥55,270 total
includes taxes & fees
Jul 9 - Jul 10
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is ￥26,718
￥46,516 total
includes taxes & fees
Jul 6 - Jul 7
Private 3 room Queen Suite w/Kitchenette
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is ￥30,605
￥38,622 total
includes taxes & fees
Jul 2 - Jul 3
Tiny Home Tranquil Oasis
Property grounds

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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is ￥11,837
￥27,138 total
includes taxes & fees
Jul 6 - Jul 7
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥36,434
￥61,303 total
includes taxes & fees
Jul 5 - Jul 6
Waterfront Retreat with Private Dock and Beach
Outdoor dining

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.
The price is ￥24,227
￥39,967 total
includes taxes & fees
Jul 13 - Jul 14
Amish Countryside Escape at Forest Edge Farm
Smart TV

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)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is ￥30,878
￥41,865 total
includes taxes & fees
Jul 13 - Jul 14
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Fridge, microwave, oven, stovetop

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.
The price is ￥33,219
￥49,001 total
includes taxes & fees
Jul 7 - Jul 8
Quarry Landing - Center of Town & River View - 3 Bedroom
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
"Everything was great. Breakfast was always fully stocked everyone was so nice from the front desk clerk to the breakfast girls to the housekeepers to the maintenance men. This is definitely going to be my go-to hotel when I'm in the area"
Sabrina 4-night trip
Posted 12 hours ago
Comfort Inn & Suites Newark - Wilmington

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

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 rental 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. Make the most of the hot tub in this rental home to help you unwind.

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 Havre de Grace Maritime Museum, 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.