Charlestown Holiday Rentals

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Holiday Rentals in Charlestown

Waterfront Historical District Home Near River
Cookware/dishes/utensils
Waterfront Historical District Home Near River
10.0 out of 10, Exceptional, 4 reviews
"House was gorgeous, clean and stocked with more necessities than I've ever seen in any others I've stayed. Gorgeous location and friendly neighborhood. Will definitely use again in the future!!! 🙂"
Waterfront Historical District Home Near River
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun-loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 37 reviews
"Our stay was amazing! Christine and Ash are wonderful hosts. Their home is lovely and very accommodating. From beautiful decor, fresh flowers and mint, to scenic bay views on the front patio and rear deck! The weather cooperated, resulting in perfect beach days and amazing sunsets on the Bay! We enjoyed dining at nearby Schaefer’s Inn and Chesapeake Inn. We look toward to our next visit! Sherry and Paul"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, 13 reviews
"We were in town for a lacrosse tournament. This property was perfect! We all enjoyed the houseboat. We all had plenty of space. The neighbors were all pleasant and the kids liked walking to the nearby ice cream shop at night. We would definitely recommend this property and stay again."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Historic Chesapeake City Stay
Pool
Historic Chesapeake City Stay
8.0 out of 10, Very good, 1 review
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is AU$366
includes taxes & fees
1 Aug - 2 Aug
Historic Chesapeake City Stay
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, 90 reviews
"Very nice very clean property. Plenty of room for my dogs to run outside. Got to meet Betsy she was very sweet and accommodating. Will definitely book again."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 20 reviews
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Property grounds
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, 45 reviews
"Owner very helpful to anything we needed. Was within walking distance to everything in town which has wonderful shops and places to eat."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Chesapeake City Overlook: Breathtaking View!
Property grounds
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely home and hostess! Very clean and responsive. Beautiful water views. Excellent vacation home"
Chesapeake City Overlook: Breathtaking View!
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, 89 reviews
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Sunset River Cottage encapsulates nautical romance.
Outdoor spa tub
Sunset River Cottage encapsulates nautical romance.
9.8 out of 10, Exceptional, 6 reviews
"This was a perfect getaway and the cottage is exactly as described. Host was able to offer pet friendly accommodations and my dogs loved the water access. A peaceful retreat in a charming character rich cottage."
Sunset River Cottage encapsulates nautical romance.
Baseball Lovers Paradise!
Interior
Baseball Lovers Paradise!
10.0 out of 10, Exceptional, 3 reviews
"Clean, easy process, beds very comfortable!"
Baseball Lovers Paradise!
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun-loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 14 reviews
"This is our fourth yearly trip to Betterton with friends and it was quite rewarding. Weather was great and the house always provides the diversity of spaces for six adults and seven kids. Looking forward to next year."
Rambling Victorian Beach House on Maryland's Eastern Shore
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Property grounds
River Haven with Hot Tub | 4 Bed, 3.5 Bath
9.8 out of 10, Exceptional, 18 reviews
"We had a wonderful weekend getaway at this property! Our group of 10 enjoyed the hot tub, fire pit, game room, and sat in the great room and on the deck enjoying the most beautiful view! The bedrooms were spacious and comfortable with private bathrooms."
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop
Clean and Cozy 2 BR home blocks away from downtown
10.0 out of 10, Exceptional, 15 reviews
"Great house, very clean. Only a short few minute walk to restaurants and shops and parks."
Clean and Cozy 2 BR home blocks away from downtown
Be persuaded to experience this vintage cottage by the Sassa
Property grounds
Be persuaded to experience this vintage cottage by the Sassa
9.0 out of 10, Wonderful, 6 reviews
"We planned a 40th birthday get a way for a friend - three couples total stayed at this wonderful home. There was plenty of space for everyone, room to hang out and a great table to playing card games. At first, we were concerned about the shared dock - but there is more than enough room for everyone out there and what a beautiful space it is. We floated in the water each day and prepared meals each night. The kitchen is very well stocked. The house was extremely clean and the hosts are so...
Be persuaded to experience this vintage cottage by the Sassa
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"House was very clean and in an excellent location. However the grounds were in need of weeding to the point that the advertised upper bay view was blocked or partially blocked from many areas. Host was prompt in responding when I reached out."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, 28 reviews
"Truly an unobstructed view of the bay. Property was very clean, and had plenty of space for 9 people (7 adults, 2 teens.) Excellent communication w/ host and well-stocked with kitchen supplies, linens, and outdoor equipment for your stay. The front porch was missing some screens and needed a little cleaning and sprucing up for the summer season. Overall, a wonderful stay, and our family made a lot of great memories at Buena Vista!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Top of the Chesapeake - Minutes from Historic Charlestown
View from property
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, 128 reviews
"Three generations from PA, CO and VT all converged on the "Top of the Chesapeake" and had a lovely time. This is a stellar place for bird watching since it's between a creek and the upper Bay ("river".) Kayaks were a hit with 12 year olds and their parents. The owner's very reasonable rules and guidelines were so easy and he was available for help. Highly recommend this place!"
The price is AU$993
includes taxes & fees
8 July - 9 July
Top of the Chesapeake - Minutes from Historic Charlestown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, 28 reviews
"Pretty house with plenty of room. Easy check in and out."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Outdoor pool, a heated pool
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 155 reviews
"This River property is a little bit of Paradise away from home! It is everything and more as advertised! My husband and I leased the property for 5 nights for a family reunion, ages 1 to 89 years old! My family of 5, my Mom, Dad and Grandmother, my brothers family of 4 and my nieces family of 3. The house was big enough for all of us to be together or everyone could have their own space. We enjoyed the pool, the hot tub, the playground and the sunsets across the river were amazing. My...
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
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See all available properties in Charlestown
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.

Charlestown Holiday Home Travel Info

Number of holiday homes
4
Popular accommodation
Charlestown private holiday homes
Known landmarks
Elk Neck State Park, Historical Society of Cecil County and Dove Valley Winery
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Charlestown you may be interested in

Red Roof Inn & Suites Newark - University
Sundeck
Red Roof Inn & Suites Newark - University
2.0 star property
5.8 out of 10, 1,006 reviews
"Well the area is save and has a lot of places to go eat"
The price is AU$128
includes taxes & fees
4 July - 5 July
Red Roof Inn & Suites Newark - University
Comfort Inn & Suites Newark - Wilmington
Desk, blackout curtains, iron/ironing board, free WiFi
Comfort Inn & Suites Newark - Wilmington
2.5 star property
9.0 out of 10, Wonderful, 1,011 reviews
"Very nice. Very clean. Worse thing was the pillows were hard. "
The price is AU$179
includes taxes & fees
8 July - 9 July
Comfort Inn & Suites Newark - Wilmington
Sonesta Select Newark Christiana Mall
Terrace/patio
Sonesta Select Newark Christiana Mall
3.0 star property
7.8 out of 10, Good, 1,008 reviews
"The stay was amazing. They upgraded my room and everyone was so nice!"
The price is AU$182
includes taxes & fees
4 July - 5 July
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.

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, 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 favourite 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 depend 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 AU$993 per night. Entering your travel dates in the search wizard might find you 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?

Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!: This holiday home rental outside of Charlestown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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 The Patriot Ice Center, or get outside and enjoy nature at Elk Neck State Park. In the wider area, you’ll find Hollywood Casino and Concord Point Lighthouse.

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.

Recent reviews of Charlestown properties
Expedia verified reviews

Holiday Inn Express & Suites Wilmington-Newark

Holiday Inn Express & Suites Wilmington-Newark

5/5 Excellent
"Food and people were great."
A verified traveller stayed at Holiday Inn Express & Suites Wilmington-Newark
Posted 10 hours ago
Holiday Inn Express & Suites Wilmington-Newark