Charlestown Vacation Rentals

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Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 17 - Oct 19
Next weekend
Oct 24 - Oct 26

Vacation Rentals in Charlestown

Outdoor dining
Chesapeake Bay House with Dock & Private Beach
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
The price is ￥26,734
￥31,567 total
includes taxes & fees
Oct 22 - Oct 23
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (11)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Terrace/patio
Nancy’s Touch, A Waterfront Paradise!
Nancy’s Touch, A Waterfront Paradise!
10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (50)
"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
Marina
Historic Chesapeake City Stay
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is ￥16,329
￥41,508 total
includes taxes & fees
Oct 23 - Oct 24
Historic Chesapeake City Stay
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm
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
1 bedroom, WiFi, bed sheets, wheelchair access
Restful Non-Shared Basement Suite In Harford MD
Restful Non-Shared Basement Suite In Harford MD
The price is ￥8,315
￥16,827 total
includes taxes & fees
Oct 19 - Oct 20
Restful Non-Shared Basement Suite In Harford MD
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Marina
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
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!!!
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown
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 ￥48,849
￥90,884 total
includes taxes & fees
Oct 15 - Oct 16
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Interior
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
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 ￥29,255
￥49,471 total
includes taxes & fees
Oct 23 - Oct 24
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Beach
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is ￥26,458
￥47,083 total
includes taxes & fees
Nov 6 - Nov 7
Waterfront Retreat with Private Dock and Beach
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis
Tiny Home Tranquil Oasis
The price is ￥28,575
￥35,909 total
includes taxes & fees
Oct 29 - Oct 30
Tiny Home Tranquil Oasis
Interior
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
6.0 out of 10, (2)
"Great stay, easy check-in, great communication "
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL
1 bedroom
Summer Rustic Camping with AC and King Bed
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 ￥14,540
￥26,909 total
includes taxes & fees
Nov 4 - Nov 5
Summer Rustic Camping with AC and King Bed
Marina
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (33)
"We loved our stay. Our family wants us to book again next year. Thank you"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

10/10 Excellent
"Overall, I was very pleased with the ES Sonesta in Newark DE. The suite was large and comfortable. Everything was in good condition. The kitchen is fully appointed. Grounds were well maintained. Staff was friendly & helpful. Breakfast was pretty good. I don't trust the pancake making machine because I don't know what the ingredients are, it's probably full oif really unhealthy stuff. And there was nothing provided to recycle cans or plastic bottles. But everything else was excellent."
Paul 2-night trip
Posted 11 hours ago
Sonesta ES Suites Wilmington - Newark

Find out more about Charlestown

Search for holiday rentals in Charlestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlestown using one of the methods below:

  • View our selection of featured holiday rentals in Charlestown
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  • Enter your travel dates to view the best deals on holiday rentals in Charlestown while they last

Look no further and take a look at our great range of rental properties in Charlestown!

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, you can find vacation rentals near popular sights in Charlestown, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Charlestown has to offer?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Charlestown is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Charlestown?

With 7 Expedia vacation rentals, you're sure 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 larger area, you’ll find Charlestown Town Hall and Hollywood Casino.

What are vacation rentals like in Charlestown?

Vacation rentals are private accommodations you can reserve for several days or more in Charlestown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.