Charlestown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Charlestown vacation rentals

Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is ￥10,987
￥17,469 total
includes taxes & fees
Mar 12 - Mar 13
Country Get Away Studio Apartment
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥16,952
￥43,758 total
includes taxes & fees
Mar 8 - Mar 9
Historic Chesapeake City Stay
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5 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 ￥11,372
￥24,117 total
includes taxes & fees
Mar 9 - Mar 10
Summer Rustic Camping with AC and King Bed
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, (2 reviews)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is ￥8,633
￥17,470 total
includes taxes & fees
Mar 13 - Mar 14
Restful Non-Shared Basement Suite In Harford MD
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
10.0 out of 10, Exceptional, (38 reviews)
"Very cool place. "
United States
Eric L.
The price is ￥27,546
￥32,526 total
includes taxes & fees
Mar 8 - Mar 9
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,656
￥27,186 total
includes taxes & fees
Mar 9 - Mar 10
Amish Countryside Escape at Forest Edge Farm
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is ￥48,075
￥75,308 total
includes taxes & fees
Mar 8 - Mar 9
Long Beach Cottage, (romantic couple’s getaway)
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, (21 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 ￥30,372
￥52,301 total
includes taxes & fees
Mar 11 - Mar 12
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Smart TV

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
9.8 out of 10, Exceptional, (8 reviews)
"Clean and comfortable. Very nice stay in the country!"
United States
Daniel B.
The price is ￥18,835
￥25,289 total
includes taxes & fees
Mar 7 - Mar 8
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Interior

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.6 out of 10, Excellent, (14 reviews)
"Great hole for our family to visit local family and celebrate Thanksgiving. Beds were comfortable house was clean and there were even Christmas lights and a tree up. So sweet. We enjoyed the fire pit and just hanging out. "
United States
Tiffany T.
The price is ￥21,190
￥44,090 total
includes taxes & fees
Mar 9 - Mar 10
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
TV

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, (13 reviews)
"Pleasant stay"
United States
Yommali G.
The price is ￥10,595
￥14,558 total
includes taxes & fees
Mar 15 - Mar 16
Charming 2-bedroom house in Aberdeen with WiFi and AC
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is ￥27,468
￥49,213 total
includes taxes & fees
Mar 8 - Mar 9
Waterfront Retreat with Private Dock and Beach
Smart TV, foosball, books

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ￥24,721
￥48,332 total
includes taxes & fees
Mar 8 - Mar 9
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
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, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥26,134
￥39,681 total
includes taxes & fees
Mar 10 - Mar 11
Quarry Landing - Center of Town & River View - 3 Bedroom
Living area

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, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is ￥23,732
￥32,643 total
includes taxes & fees
Mar 10 - Mar 11
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Interior

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is ￥15,539
￥19,378 total
includes taxes & fees
Mar 8 - Mar 9
Cozy loft above ink shop
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"Had a nice stay."
United States
Todd H.
The price is ￥27,606
￥71,175 total
includes taxes & fees
Mar 9 - Mar 10
Thunder Hill Retreat - Spacious/Deck/Hot tub
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is ￥21,974
￥40,429 total
includes taxes & fees
Mar 11 - Mar 12
Private 3 room Queen Suite w/Kitchenette
Sun loungers, beach towels

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, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is ￥40,543
￥82,241 total
includes taxes & fees
Mar 12 - Mar 13
5-bedroom vacation home 5 minutes from historic Charlestown
Outdoor dining

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
The price is ￥34,079
￥42,693 total
includes taxes & fees
Mar 8 - Mar 9
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"."
Valetta 1-night trip
Posted 8 hours ago
Fairfield Inn & Suites by Marriott Middletown

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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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?

5-bedroom vacation home 5 minutes from historic Charlestown: This vacation home near Charlestown is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games 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.