Holiday Rentals in Charlestown

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Charlestown

Waterfront cottage in historic Charlestown, Maryland

9.6 out of 10, Exceptional, (5)
"Our stay was amazing! Extremely cute and clean cottage. Water view was beautiful. Very relaxing weekend. Great communication with host. Can’t wait to go back. "
Waterfront cottage in historic Charlestown, Maryland

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

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

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (24)
"This was by far the best Property we have ever stayed at. We were in town for a cheer competition with 6 moms and 7 daughters. The upstairs room had beds for every girl plus some! The house was extremely clean and the host literally though about EVERYTHING. From local menus, to games for all ages and even to-go containers in the kitchen! (which we always forget!) It was so comfortable and enjoyable, no one wanted to leave!"
River Haven with Hot Tub | 4 Bed, 3.5 Bath

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.

Beautiful Colonial Style Home in Nottingham PA

9.6 out of 10, Exceptional, (9)
"Wonderful experience in a beautiful home. Could live there! Perfect for our entire family. Appreciate how well appointed it was with supplies, linens, etc. Could have used one more bathroom but it didn't cramp our style. Thanks to the host for a memorable vacation! "
Beautiful Colonial Style Home in Nottingham PA

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (7)
"Very clean house. Great rooms, would stay again "
Spacious North East Home w/ Fenced Yard & Fire Pit

Family Friendly Home w/ Large 1 Acre Backyard & Decks

9.4 out of 10, Exceptional, (9)
"Rented house with our 2 grandkids 6 and 15 for Thanksgiving. They especially loved the yard and it’s an easy drive into Lancaster. Lots of space and great price per night. "
Family Friendly Home w/ Large 1 Acre Backyard & Decks

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (78)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (34)
"Our family stayed here for 5 nights. The house was updated and beautiful! It was stocked with all of our basic needs and the owners quickly responded to any questions, as well as provided suggestions for local places to check out. We especially enjoyed hiking area trails, including the lighthouse, and walking and shopping in North East. It was an enjoyable and relaxing stay. Thank you for your hospitality!"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "
Chesapeake City Quiet Overlook

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

9.6 out of 10, Exceptional, (36)
"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is €283
includes taxes & fees
6 Mar - 7 Mar
Historic Chesapeake City Stay

Fair Hill Cabin-10 mins to Newark/UD

2.0 star property
10.0 out of 10, Exceptional, (1)
Fair Hill Cabin-10 mins to Newark/UD

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is €639
includes taxes & fees
18 Mar - 19 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

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

9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (52)
"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

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

9.6 out of 10, Exceptional, (4)
"Was a charming place to stay close to everything"
The price is €225
includes taxes & fees
17 Feb - 18 Feb
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.
Don't see what you're looking for?
See all available properties in Charlestown
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Charlestown you may be interested in

Quality Inn

2.5 star property
4.8 out of 10, (1002)
"Clean and was safe nice people and building needed a little work."
The price is €59
includes taxes & fees
23 Feb - 24 Feb
Quality Inn

Hilton Wilmington/Christiana

4.0 star property
8.8 out of 10, Excellent, (1000)
"Very nice hotel!"
The price is €123
includes taxes & fees
2 Mar - 3 Mar
Hilton Wilmington/Christiana

Sonesta Select Newark Christiana Mall

3.0 star property
7.8 out of 10, Good, (1001)
"Room was great and people at the front desk were really nice and friendly. "
The price is €95
includes taxes & fees
19 Feb - 20 Feb
Sonesta Select Newark Christiana Mall
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.

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?

River Haven with Hot Tub | 4 Bed, 3.5 Bath: This holiday home rental outside of Charlestown is located on a river, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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?

Fair Green Park and Veterans Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Charlestown Town Hall and Long Point Park.

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.