Charlestown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

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$387
HK$824 total
includes taxes & fees
15 Mar - 16 Mar
Restful Non-Shared Basement Suite In Harford MD
Exterior

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is HK$547
HK$870 total
includes taxes & fees
2 Mar - 3 Mar
Country Get Away 1 Bedroom Apartment
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is HK$527
HK$725 total
includes taxes & fees
28 Feb - 1 Mar
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
9.6 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 HK$467
HK$1,102 total
includes taxes & fees
24 Feb - 25 Feb
Summer Rustic Camping with AC and King Bed
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
The price is HK$727
HK$1,400 total
includes taxes & fees
23 Feb - 24 Feb
Amish Countryside Escape at Forest Edge Farm
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$844
HK$2,179 total
includes taxes & fees
23 Feb - 24 Feb
Historic Chesapeake City Stay
Interior

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
Middletown
The price is HK$563
HK$3,728 total
includes taxes & fees
23 Feb - 24 Feb
Heated Pool • Private Backyard • Home Theater
Interior

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay! "
United States
Courtney H.
The price is HK$733
HK$2,162 total
includes taxes & fees
23 Feb - 24 Feb
Hobbit House one of a kind home
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 HK$774
HK$965 total
includes taxes & fees
24 Feb - 25 Feb
Cozy loft above ink shop
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$959
HK$1,221 total
includes taxes & fees
26 Feb - 27 Feb
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$938
HK$1,259 total
includes taxes & fees
23 Feb - 24 Feb
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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 HK$1,094
HK$1,971 total
includes taxes & fees
11 Mar - 12 Mar
Private 3 room Queen Suite w/Kitchenette
Dining

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is HK$1,758
HK$3,297 total
includes taxes & fees
23 Feb - 24 Feb
Grandma’s Cottage will wrap around you like a warm hug
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 HK$1,041
HK$1,658 total
includes taxes & fees
23 Feb - 24 Feb
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior

Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
The price is HK$1,969
HK$2,339 total
includes taxes & fees
23 Feb - 24 Feb
Elegant Family Stay • Quiet Neighborhood • Comfort
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 HK$1,368
HK$2,450 total
includes taxes & fees
23 Feb - 24 Feb
Waterfront Retreat with Private Dock and Beach
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, (37 reviews)
"Very cool place. "
United States
Eric L.
The price is HK$1,371
HK$1,628 total
includes taxes & fees
23 Feb - 24 Feb
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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)
"Nice and quiet place to stay"
United States
Gary M.
The price is HK$1,055
HK$2,195 total
includes taxes & fees
23 Feb - 24 Feb
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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$1,512
HK$2,604 total
includes taxes & fees
25 Feb - 26 Feb
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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 HK$1,354
HK$3,489 total
includes taxes & fees
23 Feb - 24 Feb
Thunder Hill Retreat - Spacious/Deck/Hot tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlestown Hotel Reviews

Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

10/10 Excellent
"Staff was great "
Clifford 6-night trip
Posted 2 days ago
Red Roof Inn PLUS+ Wilmington - Newark

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
  • Use the map to find apartments and other holiday homes in the Charlestown neighbourhood you prefer
  • 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 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?

Luxury Waterfront Home Built for Entertaining!: This holiday home rental outside of Charlestown offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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.