Charlestown Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
The price is ￥11,157
￥17,739 total
includes taxes & fees
May 4 - May 5
Country Get Away Studio Apartment
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 ￥8,766
￥17,739 total
includes taxes & fees
Apr 28 - Apr 29
Restful Non-Shared Basement Suite In Harford MD
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 ￥17,213
￥44,432 total
includes taxes & fees
Apr 28 - Apr 29
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, (14 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is ￥9,897
￥13,870 total
includes taxes & fees
Apr 28 - Apr 29
Charming 2-bedroom house in Aberdeen with WiFi and AC
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, (40 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is ￥27,971
￥33,704 total
includes taxes & fees
Apr 28 - Apr 29
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,126
￥25,680 total
includes taxes & fees
Apr 28 - Apr 29
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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 ￥20,560
￥35,143 total
includes taxes & fees
May 4 - May 5
Amish Countryside Escape at Forest Edge Farm
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 ￥29,549
￥44,330 total
includes taxes & fees
May 3 - May 4
Quarry Landing - Center of Town & River View - 3 Bedroom
Outdoor dining

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is ￥21,735
￥27,313 total
includes taxes & fees
Apr 30 - May 1
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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 ￥30,840
￥52,310 total
includes taxes & fees
May 5 - May 6
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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, (6 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is ￥21,947
￥31,373 total
includes taxes & fees
Apr 28 - Apr 29
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is ￥30,123
￥37,855 total
includes taxes & fees
Apr 28 - Apr 29
Tiny Home Tranquil Oasis
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is ￥30,123
￥36,261 total
includes taxes & fees
Apr 28 - Apr 29
Nature's Haven Tiny Home
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is ￥45,783
￥73,085 total
includes taxes & fees
Apr 30 - May 1
Long Beach Cottage, (romantic couple’s getaway)
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)
"Everything was good. Had a great time."
United States
Todd H.
The price is ￥33,924
￥79,000 total
includes taxes & fees
Apr 28 - Apr 29
Thunder Hill Retreat - Spacious/Deck/Hot tub
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, (151 reviews)
"Great house for a quick little getaway with family. The house is perfect for families with children; relaxed and friendly, not fussy. Would definitely recommend."
United States
Alison R.
The price is ￥41,168
￥83,509 total
includes taxes & fees
Apr 30 - May 1
5-bedroom vacation home 5 minutes from historic Charlestown
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is ￥20,919
￥26,182 total
includes taxes & fees
May 4 - May 5
High Tide Haven Suite
Property grounds

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, (2 reviews)
"The little cottage was great! It was beautifully decorated which gave it charm. The location was perfect for our adventures to Conowingo Dam, antiquing in Havre De Grace and tastings of various breweries. We slept comfortably at the warm, quiet, clean bungalow. Coral was a fantastic host making sure we had everything we needed. We would definitely like to return. "
United States
Beth S.
The price is ￥17,213
￥30,410 total
includes taxes & fees
Apr 28 - Apr 29
Cozy 1-bedroom bungalow in quaint Darlington with AC
Interior

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
9.4 out of 10, Exceptional, (19 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveler
The price is ￥25,246
￥37,215 total
includes taxes & fees
May 3 - May 4
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Terrace/patio

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is ￥22,377
￥55,847 total
includes taxes & fees
Apr 29 - Apr 30
Private Home + 3 Bed/1.5 Bath + 2MI - 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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"We had a better stay at "
Vanessa 1-night trip
Posted 1 hour ago
Great Wolf Lodge Perryville

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.