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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

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, (43 reviews)
The price is AED 257
AED 409 total
includes taxes & fees
23 Jul - 24 Jul
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, (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 AED 202
AED 409 total
includes taxes & fees
13 Jul - 14 Jul
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, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AED 397
AED 1,032 total
includes taxes & fees
12 Jul - 13 Jul
Historic Chesapeake City Stay
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 AED 441
AED 592 total
includes taxes & fees
12 Jul - 13 Jul
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is AED 248
AED 341 total
includes taxes & fees
19 Jul - 20 Jul
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 AED 601
AED 690 total
includes taxes & fees
12 Jul - 13 Jul
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
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
9.6 out of 10, Exceptional, (4 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AED 496
AED 1,261 total
includes taxes & fees
12 Jul - 13 Jul
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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, (48 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AED 645
AED 777 total
includes taxes & fees
12 Jul - 13 Jul
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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 AED 694
AED 865 total
includes taxes & fees
12 Jul - 13 Jul
Nature's Haven Tiny Home
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 AED 721
AED 1,234 total
includes taxes & fees
13 Jul - 14 Jul
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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 AED 599
AED 950 total
includes taxes & fees
16 Jul - 17 Jul
Amish Countryside Escape at Forest Edge Farm
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 AED 694
AED 883 total
includes taxes & fees
12 Jul - 13 Jul
Tiny Home Tranquil Oasis
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, (5 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 AED 448
AED 553 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 1-bedroom bungalow in quaint Darlington with AC
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AED 303
AED 722 total
includes taxes & fees
12 Jul - 13 Jul
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is AED 520
AED 1,291 total
includes taxes & fees
3 Aug - 4 Aug
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
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, (21 reviews)
"Beautiful, rustic apartment on a farm was the perfect relaxing environment we needed for the weekend. Loved walking around the wooded grounds and meeting the farm animals. The apartment itself was spacious, clean, and comfortable. Will definitely try to cone back. "
United States
Jeff J.
The price is AED 582
AED 862 total
includes taxes & fees
12 Jul - 13 Jul
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
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 AED 826
AED 1,391 total
includes taxes & fees
12 Jul - 13 Jul
Waterfront Retreat with Private Dock and Beach
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 AED 891
AED 1,969 total
includes taxes & fees
14 Jul - 15 Jul
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, (32 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is AED 606
AED 1,055 total
includes taxes & fees
19 Jul - 20 Jul
Private 3 room Queen Suite w/Kitchenette
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
"This was a great experience for myself and my family, the room was very clean and spacious enough for us, the concierge was next to none. I appreciate the service and great hospitatlity of everyone who we encountered that worked there and we are excited to go back soon."
Angela 3-night trip
Posted less than an hour ago
Great Wolf Lodge Perryville

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. 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 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.