Holiday Rentals in Charlestown

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Our top choices for Charlestown holiday rentals

Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (2 reviews)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is €98
includes taxes & fees
12 May - 13 May
Restful Non-Shared Basement Suite In Harford MD

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is €240
includes taxes & fees
19 May - 20 May
Historic Chesapeake City Stay

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is €98
includes taxes & fees
18 May - 19 May
Country Get Away Studio Apartment

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (15 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is €83
includes taxes & fees
12 May - 13 May
Charming 2-bedroom house in Aberdeen with WiFi and AC

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

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is €182
includes taxes & fees
12 May - 13 May
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is €141
includes taxes & fees
12 May - 13 May
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is €206
includes taxes & fees
12 May - 13 May
Tiny Home Tranquil Oasis

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is €197
includes taxes & fees
12 May - 13 May
Nature's Haven Tiny Home

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is €260
includes taxes & fees
26 May - 27 May
Quarry Landing - Center of Town & River View - 3 Bedroom

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (7 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is €174
includes taxes & fees
12 May - 13 May
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is €185
includes taxes & fees
18 May - 19 May
Amish Countryside Escape at Forest Edge Farm

Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (2 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
Cozy 1-bedroom bungalow in quaint Darlington with AC

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"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 €164
includes taxes & fees
10 Jun - 11 Jun
Summer Rustic Camping with AC and King Bed

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is €161
includes taxes & fees
31 May - 1 Jun
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (2 reviews)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is €157
includes taxes & fees
18 May - 19 May
High Tide Haven Suite

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
Newark
9.6 out of 10, Exceptional, (21 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.4 out of 10, Exceptional, (19 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveller
The price is €199
includes taxes & fees
12 May - 13 May
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Beachcomber Suite

Beachcomber Suite
Kent County
The price is €157
includes taxes & fees
18 May - 19 May
Beachcomber Suite

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is €423
includes taxes & fees
14 May - 15 May
Thunder Hill Retreat - Spacious/Deck/Hot tub
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

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, apart-hotels, 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 €83 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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Charlestown is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.