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Top Holiday Rentals in Charlestown

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is £210
includes taxes & fees
24 Aug - 25 Aug
Historic Chesapeake City Stay

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat

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

9.6 out of 10, Exceptional, (5)
"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 £1,013
includes taxes & fees
20 Aug - 21 Aug
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

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

9.4 out of 10, Exceptional, (30)
"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.

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

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

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"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 £128
includes taxes & fees
21 Aug - 22 Aug
Summer Rustic Camping with AC and King Bed

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

The Chalet is located in the woods of a gated property with a covered porch.

9.4 out of 10, Exceptional, (22)
"Beautiful little house, great surroundings. We live every minute."
The Chalet is located in the woods of a gated property with a covered porch.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake

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

9.2 out of 10, Wonderful, (5)
The price is £236
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Charming, updated 1930's beachfront cottage with stunning sunset views

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Charming, updated 1930's beachfront cottage with stunning sunset views

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (49)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

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

10.0 out of 10, Exceptional, (18)
"Was a charming place to stay close to everything"
The price is £156
includes taxes & fees
25 Aug - 26 Aug
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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

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.