Charlestown Holiday Rentals

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Our top choices for Charlestown holiday rentals

10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$348
includes taxes & fees
12 Jan - 13 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (33)
"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"
United States
Xiaodong F.
The price is AU$317
includes taxes & fees
3 Jan - 4 Jan 2026
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
Thunder Hill Retreat - Spacious/Deck/Hot tub

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"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 AU$372
includes taxes & fees
29 Dec - 30 Dec
Historic Chesapeake City Stay
9.8 out of 10, Exceptional, (8)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$243
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
9.4 out of 10, Exceptional, (3)
"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 AU$504
includes taxes & fees
29 Dec - 30 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
10.0 out of 10, Exceptional, (2)
"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 AU$169
includes taxes & fees
25 Jan - 26 Jan 2026
Restful Non-Shared Basement Suite In Harford MD
9.2 out of 10, Wonderful, (13)
"We had an excellent stay"
United States
Meagan
The price is AU$353
includes taxes & fees
4 Jan - 5 Jan 2026
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$169
includes taxes & fees
6 Jan - 7 Jan 2026
Country Get Away 1 Bedroom Apartment
9.6 out of 10, Exceptional, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
8.2 out of 10, Very good, (12)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$412
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
10.0 out of 10, Exceptional, (4)
"Enjoyed our stay."
United States
Erik H.
The price is AU$415
includes taxes & fees
4 Jan - 5 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
9.6 out of 10, Exceptional, (5)
"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 AU$254
includes taxes & fees
19 Jan - 20 Jan 2026
Summer Rustic Camping with AC and King Bed
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$514
includes taxes & fees
1 Jan - 2 Jan 2026
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Apartment in Bear

Cozy loft above ink shop
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is AU$176
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy loft above ink shop
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AU$468
includes taxes & fees
6 Jan - 7 Jan 2026
Waterfront Retreat with Private Dock and Beach
The price is AU$627
includes taxes & fees
30 Dec - 31 Dec
Grandma’s Cottage will wrap around you like a warm hug
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is AU$758
includes taxes & fees
7 Jan - 8 Jan 2026
Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is AU$388
includes taxes & fees
5 Jan - 6 Jan 2026
Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
The price is AU$1,624
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 4-bedroom house with backyard oasis
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

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 favourite 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 depend 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 AU$243 per night. Entering your travel dates in the search wizard might find you 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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Charlestown is located on the beach, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Plumpton Park Zoo, 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.