Charlestown Holiday Rentals

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Our top choices for Charlestown holiday rentals

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 NZ$461
includes taxes & fees
2 Mar - 3 Mar
Historic Chesapeake City Stay

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 NZ$155
includes taxes & fees
2 Mar - 3 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$186
includes taxes & fees
9 Mar - 10 Mar
Country Get Away 1 Bedroom Apartment

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 NZ$269
includes taxes & fees
2 Mar - 3 Mar
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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 NZ$239
includes taxes & fees
2 Mar - 3 Mar
Summer Rustic Camping with AC and King Bed

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 NZ$349
includes taxes & fees
5 Mar - 6 Mar
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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 NZ$356
includes taxes & fees
2 Mar - 3 Mar
Quarry Landing - Center of Town & River View - 3 Bedroom

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 NZ$186
includes taxes & fees
13 Mar - 14 Mar
Restful Non-Shared Basement Suite In Harford MD

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 NZ$798
includes taxes & fees
8 Mar - 9 Mar
Long Beach Cottage, (romantic couple’s getaway)

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
The price is NZ$294
includes taxes & fees
2 Mar - 3 Mar
Amish Countryside Escape at Forest Edge Farm

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 NZ$546
includes taxes & fees
11 Mar - 12 Mar
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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 NZ$318
includes taxes & fees
2 Mar - 3 Mar
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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 NZ$510
includes taxes & fees
2 Mar - 3 Mar
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

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 NZ$465
includes taxes & fees
2 Mar - 3 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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 NZ$735
includes taxes & fees
2 Mar - 3 Mar
Thunder Hill Retreat - Spacious/Deck/Hot tub

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 NZ$206
includes taxes & fees
2 Mar - 3 Mar
Cozy loft above ink shop

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 NZ$510
includes taxes & fees
8 Mar - 9 Mar
Waterfront Retreat with Private Dock and Beach

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is NZ$336
includes taxes & fees
2 Mar - 3 Mar
High Tide Haven Suite

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 NZ$867
includes taxes & fees
2 Mar - 3 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

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 NZ$428
includes taxes & fees
12 Mar - 13 Mar
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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Find out more about Charlestown

Everything you need to know about Charlestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Charlestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Charlestown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Charlestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Charlestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Charlestown holiday rentals we have selected for you start as low as NZ$155 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Charlestown rentals

At Expedia, we put the best Charlestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Charlestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Charlestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Charlestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

5-bedroom vacation home 5 minutes from historic Charlestown: This holiday home rental outside of Charlestown is located on a river, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games 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.