Charlestown Holiday Rentals

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Check prices for these dates

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Holiday Rentals in Charlestown

Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Holiday Home in Perryville

10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Outdoor dining
Chesapeake Bay House with Dock & Private Beach

Holiday Home in Elkton

10.0 out of 10, Exceptional, (178)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Holiday Home in Abingdon

8.0 out of 10, Very good, (5)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is HK$3,854
HK$6,470 total
includes taxes & fees
2 Dec - 3 Dec
Luxury Waterfront Home Built for Entertaining!
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is HK$1,366
HK$1,630 total
includes taxes & fees
2 Dec - 3 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Holiday Home in Elkton

9.8 out of 10, Exceptional, (43)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Private kitchen
Room #3 in Elkton, MD – Easy Access to I-95

Holiday Home in Elkton

2.0 star property
The price is HK$662
HK$1,032 total
includes taxes & fees
2 Dec - 3 Dec
Room #3 in Elkton, MD – Easy Access to I-95
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Cottage in Elkton

9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Fridge, microwave, oven, stovetop
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Holiday Home in Havre de Grace

9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
The price is HK$6,306
HK$10,464 total
includes taxes & fees
2 Dec - 3 Dec
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Cottage in Earleville

9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

Holiday Home in Perryville

9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is HK$2,515
HK$4,622 total
includes taxes & fees
8 Dec - 9 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm

Cabin in Elkton

9.6 out of 10, Exceptional, (14)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Fridge, microwave, oven, stovetop
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Holiday Home in Chesapeake City

10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis

Mobile Home in Bear

Tiny Home Tranquil Oasis
Marina
Historic Chesapeake City Stay

Cabin in Chesapeake City

9.0 out of 10, Wonderful, (18)
"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 HK$841
HK$2,170 total
includes taxes & fees
2 Dec - 3 Dec
Historic Chesapeake City Stay
1 bedroom
Summer Rustic Camping with AC and King Bed

Holiday Home in Elkton

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 HK$546
HK$1,178 total
includes taxes & fees
2 Dec - 3 Dec
Summer Rustic Camping with AC and King Bed
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Cottage in Port Deposit

10.0 out of 10, Exceptional, (11)
"Very clean, spacious, comfortable house. Would stay there again. Great communication with the hosts."
United States
Courtney W.
The price is HK$1,037
HK$1,660 total
includes taxes & fees
2 Dec - 3 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom
Beach
Captivating Chesapeake experience

Holiday Home in Perryville

10.0 out of 10, Exceptional, (279)
"Nothing more beautiful than staying by the water at Joe’s place!Such a wonderful place to unwind and refuel!"
United States
Doreen H.
Captivating Chesapeake experience
Fridge, microwave, oven, stovetop
Tip Of The Town Fresh and New 3 Bedroom Nest

Holiday Home in North East

10.0 out of 10, Exceptional, (26)
"we had a really nice timeeverything was clean and fresh when we arrived"
United States
devora a.
Tip Of The Town Fresh and New 3 Bedroom Nest
Property grounds
Country Get Away 1 Bedroom Apartment

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is HK$545
HK$866 total
includes taxes & fees
8 Dec - 9 Dec
Country Get Away 1 Bedroom Apartment
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.

Villa in Earleville

9.8 out of 10, Exceptional, (19)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.
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

Hilton Wilmington/Christiana

Hilton Wilmington/Christiana

10/10 Excellent
"Excellent hotel!"
Natacha 1-night trip
Posted 1 day ago
Hilton Wilmington/Christiana

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 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Charlestown is located on a river, and has a patio, a garden 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 can relax into your holiday with a selection of games and 1 hot tub.

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.