Charlestown Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Charlestown holiday rentals

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 HK$431
HK$872 total
includes taxes & fees
4 Jun - 5 Jun
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, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$940
HK$2,317 total
includes taxes & fees
10 Jun - 11 Jun
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is HK$548
HK$872 total
includes taxes & fees
22 Jun - 23 Jun
Country Get Away Studio Apartment
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.2 out of 10, Very good, (17 reviews)
"Nice place"
United States
christine
The price is HK$744
HK$955 total
includes taxes & fees
13 Jun - 14 Jun
Charming 2-bedroom house in Aberdeen with WiFi and AC
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, (6 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 HK$757
HK$1,393 total
includes taxes & fees
23 Jun - 24 Jun
Summer Rustic Camping with AC and King Bed
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 HK$940
HK$1,262 total
includes taxes & fees
28 May - 29 May
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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, (9 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 HK$1,178
HK$1,631 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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 HK$909
HK$1,601 total
includes taxes & fees
10 Jun - 11 Jun
Amish Countryside Escape at Forest Edge Farm
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, (43 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is HK$1,375
HK$1,632 total
includes taxes & fees
1 Jun - 2 Jun
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit 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
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 HK$1,058
HK$2,666 total
includes taxes & fees
7 Jun - 8 Jun
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Exterior

Luxury Bed and Breakfast Suite for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast Suite for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
The price is HK$1,269
HK$1,452 total
includes taxes & fees
28 May - 29 May
Luxury Bed and Breakfast Suite for a Weekend Getaway near Susquehanna State Park, Maryland
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 HK$1,516
HK$2,571 total
includes taxes & fees
28 May - 29 May
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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)
"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 HK$940
HK$1,163 total
includes taxes & fees
31 May - 1 Jun
Cozy 1-bedroom bungalow in quaint Darlington with AC
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 HK$1,235
HK$1,535 total
includes taxes & fees
7 Jun - 8 Jun
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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 HK$1,481
HK$1,829 total
includes taxes & fees
2 Jun - 3 Jun
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, (20 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is HK$1,675
HK$3,892 total
includes taxes & fees
1 Jun - 2 Jun
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, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,097
HK$1,976 total
includes taxes & fees
22 Jun - 23 Jun
Private 3 room Queen Suite w/Kitchenette
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, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,474
HK$2,160 total
includes taxes & fees
28 May - 29 May
Quarry Landing - Center of Town & River View - 3 Bedroom
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, (20 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveller
The price is HK$1,241
HK$1,838 total
includes taxes & fees
28 May - 29 May
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Beach

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 HK$1,763
HK$2,967 total
includes taxes & fees
15 Jun - 16 Jun
Waterfront Retreat with Private Dock and Beach
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

8/10 Good
"My experience was pleasurable and entertaining."
Verna 1-night trip
Posted less than an 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:

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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 holiday rental in Charlestown?

Yes, there are holiday rentals close to the most popular sights in Charlestown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Charlestown has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Charlestown?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Charlestown Town Hall and Hollywood Casino.

What are holiday rentals like in Charlestown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Charlestown. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a small group gathering.