Charlestown Holiday Rentals

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Holiday Rentals in Charlestown

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (263)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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

10.0 out of 10, Exceptional, (2)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is NZ$1,481
includes taxes & fees
29 June - 30 June
Luxury Waterfront Home Built for Entertaining!

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

10.0 out of 10, Exceptional, (1)
"Good experience"
The price is NZ$901
includes taxes & fees
29 June - 30 June
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

9.2 out of 10, Wonderful, (174)
"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

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (19)
"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

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

9.8 out of 10, Exceptional, (40)
"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

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

9.4 out of 10, Exceptional, (25)
"We were a group of all ages and everyone had a good time. It was quiet, peaceful and very relaxing. We were there for a baseball tournament and would definitely stay again."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is NZ$618
includes taxes & fees
1 July - 2 July
Waterfront Retreat with Private Dock and Beach

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (88)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"My friends and I wanted a relaxing getaway with beautiful views and that is exactly what we got. Sue was so wonderful and when there was a massive snowstorm expected to come on our arrival date, she offered to change the dates to accommodate us. Everything was wonderful and we had the best stay."
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (161)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is NZ$1,007
includes taxes & fees
1 July - 2 July
5-bedroom vacation home 5 minutes from historic Charlestown

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is NZ$387
includes taxes & fees
29 June - 30 June
Nature's Haven Tiny Home

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

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

10.0 out of 10, Exceptional, (14)
"Was a charming place to stay close to everything"
The price is NZ$344
includes taxes & fees
29 June - 30 June
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (47)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Sailor's Sunrise Cottage - Chesapeake Bay

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay. Everything you need, quiet and clean. "
The price is NZ$266
includes taxes & fees
29 June - 30 June
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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

9.6 out of 10, Exceptional, (57)
"Great place. Accurately depicted in photos. Nice quiet neighborhood. Super dog friendly!"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
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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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 BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals will I find in Charlestown?

With 8 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 Milburn Stone Theater.

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.