Charlestown holiday rentals

We found 156 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Charlestown that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Charlestown

Showing deals for:6 Nov - 13 Nov

Exterior
Living area
Private kitchen
Overlook bridge to a private deck overlooking the water
Exceptional
(6 reviews)

Vintage Waterfront Cottage with Stunning Sunsets

North East

8% off
AU$3,756
for 7 nights, 1 cottage
AU$537 per night
includes taxes & fees
Vintage Waterfront Cottage with Stunning Sunsets
Living Room
Outdoor dining
Kitchen Island
Property grounds
Exceptional
(189 reviews)

Chesapeake Bay House with Dock & Private Beach

Elkton

8% off
AU$6,417
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Chesapeake Bay House with Dock & Private Beach
Private Pool
Chesapeake a few minutes walk
Private kitchen
Kitchen with large island & seating
Exceptional
(10 reviews)

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City

8% off
AU$7,507
for 7 nights, 1 home
AU$1,072 per night
includes taxes & fees
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
Interior
Exterior
Room
Dining
Exceptional
(47 reviews)

Waterfront Retreat for Weekends and More!

Elkton

19% off
AU$3,878
for 7 nights, 1 home
AU$554 per night
includes taxes & fees
Waterfront Retreat for Weekends and More!
Living room with pullout sofa bed,  large Smart TV and half bath access
Updated kitchen with Quartz countertops, Corian backsplashes and SS appliances
Buffet serving area between kitchen and dining room
Wet bar in dining room
Exceptional
(82 reviews)

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City

13% off
AU$3,667
for 7 nights, 1 home
AU$524 per night
includes taxes & fees
Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Interior
Property grounds
Beautiful Sunsets!  No filters!
Interior
Exceptional
(92 reviews)

Bonfire by the Creek

North East

27% off
AU$2,046
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Bonfire by the Creek
Private kitchen
Terrace/patio
Room
Living area
Exceptional
(6 reviews)

Chesapeake Waterfront Vacation Rental with Dock - SunriseHavenMD

Perryville

8% off
AU$4,357
for 7 nights, 1 home
AU$622 per night
includes taxes & fees
Chesapeake Waterfront Vacation Rental with Dock - SunriseHavenMD
Exterior detail
Living area
Interior
Private kitchen
Exceptional
(70 reviews)

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville

8% off
AU$1,982
for 7 nights, 1 cottage
AU$283 per night
includes taxes & fees
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Living area
Property grounds
Private kitchen
Lake
Exceptional
(293 reviews)

Captivating Chesapeake experience

Perryville

9% off
AU$3,234
for 7 nights, 1 home
AU$462 per night
includes taxes & fees
Captivating Chesapeake experience
Interior
Interior
Exterior
Lobby
Exceptional
(12 reviews)

Comfortable and quiet 3-bedroom-walk to downtown

Havre De Grace

7% off
AU$3,755
for 7 nights, 1 home
AU$536 per night
includes taxes & fees
Comfortable and quiet 3-bedroom-walk to downtown
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Charlestown getaway

Learn about the unique charm of Charlestown with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Charlestown

Are you hoping to discover things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Charlestown has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Dove Valley Winery (7.7 mi / 12.3 km)
  • Bulle Rock Golf Course (8.7 mi / 14 km)
  • Back Creek Golf Club (12.5 mi / 20.2 km)
  • Wyncote Golf Club (16.5 mi / 26.6 km)
  • Mount Felix Vineyard & Winery (8.1 mi / 13 km)
  • Plumpton Park Zoo (9.1 mi / 14.7 km)

Exploring the natural landscape of Charlestown

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Charlestown. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • North East Beach Area (5.6 mi / 9 km)
  • Meadow Park (8.4 mi / 13.5 km)
  • Fair Hill State Natural Resources Management Area (11.9 mi / 19.1 km)
  • Lewis Park (13.8 mi / 22.2 km)
  • University of Delaware Botanic Gardens (13.9 mi / 22.3 km)
  • Betterton Beach (14.8 mi / 23.8 km)

Transport to and around Charlestown

Fly into Wilmington, DE (ILG-New Castle), the closest airport, located 21.3 mi (34.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore, MD (MTN-Martin State), which is 29.2 mi (47 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Charlestown?
Houses are the most popular style of holiday home in Charlestown, according to our data. Even if you have a different idea about what you'd like, Stayz has holiday homes in a variety of sizes and shapes. Compare our options to find your perfect Charlestown pad.
How much does it cost to rent a holiday home in Charlestown?
Length of stay, property type and season are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy cabins to sprawling luxury villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Charlestown?
The average price for a holiday home by the beach in Charlestown will depend on when you'll be there and the style and size of property you're looking for. You can quickly and easily find prices on Stayz by entering your destination and preferred travel dates. Then use our filters to select the number of bedrooms and amenities essential to you, like a pool, WiFi and air conditioning.
Are there pet-friendly holiday homes in Charlestown?
There are, yes. You'll have a choice of three holiday homes that allow pets in Charlestown on Stayz. Our furry kids need to get away from it all too, so simply use our search function for pet-friendly holiday homes to find a perfect pad where your puppy can join the fun.
What are popular home amenities in Charlestown?
A garden, a nearby river and a swimming pool rank as the most popular home amenities in Charlestown. Whether you're taking a trip solo, with your spouse or a bunch of friends, Stayz will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday homes in Charlestown?
With two Charlestown properties that can accommodate five or more people, you can invite a few extra family members or pals along. Whether you're planning a casual gathering or a birthday party, we'll help you book a comfortable space to match the occasion.
Are there holiday homes in Charlestown that welcome kids?
With three family-friendly holiday homes to select from in Charlestown, now is a superb time to introduce the kiddos to the thrills of travel. Just click on our "Properties good for families" filter box to search for stays packed with amenities perfect for holidaying families, such as dining rooms, private pools, bunk beds and entertainment areas.
What are the top attractions for families in Charlestown?
Keep your kids busy at these fantastic family-friendly attractions in Charlestown:
  • Havre de Grace Maritime Museum
  • Plumpton Park Zoo
  • Historical Society of Cecil County
How can I find holiday homes with air conditioning in Charlestown?
There are three holiday homes with air conditioning in Charlestown offering that cool, cool breeze and extra element of comfort. Just enter your dates of travel and then use our filters to help you book stays with air conditioning.
How old do you have to be to rent a holiday home in Charlestown?
The minimum required age is normally 16, 18 or 21. It can vary from one property to another on Stayz, so check the rules of your chosen Charlestown holiday home before booking.
How long can I rent a holiday home in Charlestown for?
The amount of time you can book a Charlestown holiday home for is up to each property. Just put in your dates of travel to browse available options that offer extended stays. They feature all you need to make your extended holiday more comfortable and convenient, such as kitchens and backyards. Some properties might also offer discounted weekly or monthly prices, so you can have a longer stay for less.

More holiday ideas