Charlestown Holiday Rentals

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Holiday Rentals in Charlestown

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (24)
"Very nice cottage, as advertised"
The price is NZ$360
includes taxes & fees
5 Oct - 6 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (33)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is NZ$573
includes taxes & fees
5 Oct - 6 Oct
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"Everything about this rental was easy, from check in to departure. We had one challenge with the TV and the host answered my text immediately and solved the issue for us. House was clean and as described in the listing. Highly recommend. "
Waterfront house with amazing views. Top of the Chesapeake

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is NZ$479
includes taxes & fees
5 Oct - 6 Oct
Historic Chesapeake City Stay

Restful Non-Shared Basement Suite In Harford MD

The price is NZ$191
includes taxes & fees
12 Oct - 13 Oct
Restful Non-Shared Basement Suite In Harford MD

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (169)
"Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. "
Nancy’s Touch, A Waterfront Paradise!

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (48)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (2)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (276)
"We had such a great weekend at this property. It was beautiful and such a relaxing location. House had everything we needed. We hope to be back!! "
Captivating Chesapeake experience

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is NZ$1,040
includes taxes & fees
8 Oct - 9 Oct
5-bedroom vacation home 5 minutes from historic Charlestown

Tiny Home Tranquil Oasis

The price is NZ$406
includes taxes & fees
24 Oct - 25 Oct
Tiny Home Tranquil Oasis

Summer Rustic Camping with AC and King Bed

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."
The price is NZ$301
includes taxes & fees
8 Oct - 9 Oct
Summer Rustic Camping with AC and King Bed

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed this cottage and location for weekend during lacrosse tournaments. Much better than staying in hotel and perfect on the water to enjoy some family time! Thanks Angela! "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

2.0 star property
9.6 out of 10, Exceptional, (9)
"We had an excellent stay"
The price is NZ$401
includes taxes & fees
8 Oct - 9 Oct
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

9.8 out of 10, Exceptional, (6)
"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"
The price is NZ$2,310
includes taxes & fees
4 Oct - 5 Oct
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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

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$191 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?

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 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.