Best Vacation Homes in Charlestown
House
10.0(288 Reviews)
2 Bedrooms
2 Baths
6 Guests
1456 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $334/Night
7 Nights - US $2,337
House
10.0(1 Review)
3 Bedrooms
3 Baths
7 Guests
1496.18 ft²
- Fireplace/Heating
Parking
Internet
Child Friendly
US $338/Night
7 Nights - US $2,368
Cabin
8.8(3 Reviews)
1 Bedroom
1 Bath
Oceanfront- Fireplace/Heating
Pool
Ocean View
US $424/Night
7 Nights - US $2,967
House
10.0(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $239/Night
7 Nights - US $1,672
House
1 Bedroom
1 Bath
2 Guests
602.78 ft²
Hot Tub- Fireplace/Heating
View
Air Conditioner
US $446/Night
7 Nights - US $3,124
House
10.0(33 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $226/Night
7 Nights - US $1,585
Cottage
10.0(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $307/Night
7 Nights - US $2,147
House
10.0(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $229/Night
7 Nights - US $1,601
Charlestown Luxury Rentals
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
US $1,719/Night
7 Nights - US $12,034
New
House
1 Bedroom
1 Bath
5 Guests
355.21 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,310/Night
7 Nights - US $9,168
House
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,309/Night
7 Nights - US $9,165
House
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,309/Night
7 Nights - US $9,165
House
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,309/Night
7 Nights - US $9,165
New
House
1 Bedroom
1 Bath
4 Guests
301.39 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,292/Night
7 Nights - US $9,046
House
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,290/Night
7 Nights - US $9,033
House
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,290/Night
7 Nights - US $9,033
Charlestown Pet Friendly Vacation Rentals
House
10.0(174 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $481/Night
7 Nights - US $3,364
House
10.0(26 Reviews)
5 Bedrooms
4 Baths
16 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $806/Night
7 Nights - US $5,642
House
9.8(151 Reviews)
5 Bedrooms
2 Baths
13 Guests
2600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $497/Night
7 Nights - US $3,480
House
9.4(54 Reviews)
3 Bedrooms
1 Bath
6 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $281/Night
7 Nights - US $1,965
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $411/Night
7 Nights - US $2,875
House
1 Bedroom
1 Bath
2 Guests
3434 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $614/Night
7 Nights - US $4,298
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- View
- Pet Friendly
- Child Friendly
US $600/Night
7 Nights - US $4,200
House
3 Bedrooms
2 Baths
8 Guests
1730 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $422/Night
7 Nights - US $2,953
Charlestown Large Vacation Homes
House
10.0(22 Reviews)
3 Bedrooms
3 Baths
11 Guests
1702 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $398/Night
7 Nights - US $2,783
House
5 Bedrooms
3 Baths
10 Guests
1991.32 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $500/Night
7 Nights - US $3,500
House
10.0(20 Reviews)
5 Bedrooms
3 Baths
10 Guests
1990 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $445/Night
7 Nights - US $3,115
House
10.0(3 Reviews)
5 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $916/Night
7 Nights - US $6,411
House
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
1872 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $472/Night
7 Nights - US $3,302
House
9.6(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $370/Night
7 Nights - US $2,592
House
10.0(1 Review)
5 Bedrooms
4 Baths
8 Guests
2993 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $557/Night
7 Nights - US $3,896
Villa
10.0(7 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Pet Friendly
- Kitchen
- Internet
- Child Friendly
US $600/Night
7 Nights - US $4,200
Why Choose Rent By Owner for your Charlestown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Charlestown
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as the weather and local events in this region vary throughout the year, making certain seasons ideal for enjoying your stay in the area’s beautiful surroundings.
Peak Season Highlights
Late Spring (May to June)
During late spring, you'll enjoy pleasant weather ideal for outdoor activities and exploring this destination’s natural beauty. The region sees a surge in visitors seeking comfortable vacation rentals that offer a peaceful retreat.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Summer (July to August)
Summer is the most popular time to visit, with warm temperatures and longer daylight hours perfect for outdoor pursuits. Booking your vacation rentals early ensures you secure accommodations during this busy season here.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Off-Season Highlights
Early Spring (March to April)
In early spring, the area begins to blossom, offering a quieter time to enjoy this destination’s scenic surroundings. It’s an excellent opportunity to find more affordable vacation rentals with less competition.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F
Fall (September to October)
Autumn brings cooler temperatures and vibrant foliage, making it a perfect season for those seeking a peaceful escape. You can often discover budget-friendly vacation rentals when visiting during these months.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Weekly Weather Forecast for Charlestown
How to Book Your Charlestown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Charlestown
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck ideal for relaxing and entertaining amidst natural surroundings.
- Take advantage of spacious yards or gardens perfect for outdoor activities or family gatherings.
- Make the most of outdoor grilling areas to savor local flavors in a scenic setting.
- Find properties equipped with access to nearby parks or green spaces for nature walks and outdoor recreation.
- Benefit from outdoor seating areas that provide comfortable spots to unwind while enjoying the fresh air.
- Discover vacation rentals with swimming pools or hot tubs for year-round outdoor relaxation.
- Opt for accommodations offering proximity to waterfronts or lakes for kayaking, fishing, or boating adventures.
Top Attractions Around Charlestown
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities, scenic parks, and local attractions that showcase the natural beauty and rich history nearby your vacation rental in Charlestown, Maryland.
Family Activities
- Patuxent River State Park: Explore nature trails, enjoy birdwatching, and participate in family-friendly outdoor activities within this tranquil park near the area.
- Historic Charlestown Town Center: Discover local heritage and charming shops that offer a glimpse into the area's history, making it an educational outing for all ages.
- Riverside Boat Tours: Experience scenic boat excursions along the Patuxent River, providing memorable adventures and stunning views suitable for family outings.
- Local Farmers Markets: Visit farmers markets that showcase fresh produce and artisan goods, offering a delightful experience for families to enjoy together here in the region.
Adult Activities
- Explore Historic Downtown Charlestown: Take a leisurely stroll through the charming streets filled with local shops and historic landmarks, immersing yourself in the area's rich heritage.
- Visit the Waterfront Park: Relax by the scenic shoreline where you can enjoy panoramic views of the region’s waterways and partake in peaceful riverfront activities.
- Discover Local Art Galleries: Appreciate the vibrant arts scene by touring the area's galleries showcasing regional artists and unique craftsmanship.
- Enjoy Outdoor Recreation: Engage in activities like kayaking or fishing at nearby waterways, offering a refreshing way to experience the natural beauty of this destination.
Charlestown Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or seasonal activities that enrich your experience here.
- Explore Unique Neighborhoods: Take time to discover the charming neighborhoods surrounding the region, offering authentic dining and shopping options close to your vacation rental.
- Utilize Natural Settings: Make the most of outdoor adventures by exploring nearby parks or waterways that showcase the area's natural beauty during your visit.
- Engage with Local Resources: Reach out to community centers or visitor information points to uncover hidden gems and insider tips for a memorable stay in this destination.
Transportation Options
- Personal Vehicles: Renting or driving your own car offers the most flexibility to explore the area at your own pace.
- Public Transportation: Local buses provide an economical and convenient way to get around here without the hassle of parking.
- Taxi and Rideshare Services: Options like taxis and rideshare apps are readily available for quick, door-to-door transportation in this destination.
- Biking and Pedestrian Paths: Biking is a popular choice in the region, with well-maintained paths that allow you to enjoy the scenery while traveling locally.
Local Customs Options
- Boat Building Tradition: Locally, boat building is a cherished custom that reflects the area's maritime history and can often be seen during community events.
- Seafood Cuisine: Savoring fresh seafood, especially Chesapeake Bay oysters, is a widespread tradition embraced by residents and visitors alike in this region.
- Historic Preservation: Maintaining historic structures and sites is a key aspect of local pride, providing a glimpse into the area's rich cultural heritage here.
Charlestown Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Charlestown?
There are a lot of options in Charlestown. If you plan on staying in the Charlestown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Charlestown:
- Captivating Chesapeake experience
- Nancy’s Touch, A Waterfront Paradise!
- Waterfront house with amazing views. Top of the Chesapeake
- Water View House in Charlestown, MD
- Charming Cottage in Historic Charlestown, MD - Marina & Beach Access
- Historic Creekside Home - 2br 2.5ba - Downtown North East
- Clean and Cozy 2 BR home blocks away from downtown
- Tip Of The Town Fresh and New 3 Bedroom Nest
- Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
- Charming Waterfront Cottage with Private Boat Dock
2. How many vacation rentals have private pools in Charlestown?
There are 1 vacation rentals with private pools near Charlestown. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Charlestown are best for families?
If you are looking for a family-friendly vacation home in Charlestown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Charlestown:
4. How many Rentbyowner vacation rentals are available in Charlestown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 172 in the Charlestown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Charlestown.
5. What is the cancellation policy for properties in Charlestown, Maryland?
Cancellation policies vary depending on the specific listing. You should review the cancellation details listed on the property page or contact the owner directly for precise information.
6. How do I ensure my booking in this destination is secure?
Bookings are secured through the platform's trusted reservation system. For added peace of mind, check the property's reviews and communicate with the owner prior to finalizing your reservation.
7. Are there any additional fees I should be aware of when booking here?
Additional fees, such as cleaning or service charges, are typically specified during the booking process. Always review the total cost breakdown provided before confirming your reservation.
8. What amenities can I expect in a vacation rental here?
Amenities vary by property but may include essentials like Wi-Fi, parking, and kitchen facilities. For specifics, refer to the property listing details or contact the owner directly.
9. Is there a minimum night stay requirement for booking here?
Minimum stay requirements depend on the individual property and seasonality. Details are available in the listing description, or you can inquire directly with the owner for clarification.
Charlestown Top Rated Vacation Rentals
US $483/Night
7 Nights - US $3,384
Resort
10.0(1 Review)
1 Bath
6 Guests
400 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $422/Night
7 Nights - US $2,956
Resort
9.6(9 Reviews)
1 Bath
8 Guests
400 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $380/Night
7 Nights - US $2,662
House
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,290/Night
7 Nights - US $9,033
House
1 Bedroom
1 Bath
5 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,290/Night
7 Nights - US $9,033
New
House
1 Bedroom
1 Bath
5 Guests
355.21 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,286/Night
7 Nights - US $9,005
House
1 Bedroom
1 Bath
5 Guests
301.39 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,284/Night
7 Nights - US $8,987
House
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $1,265/Night
7 Nights - US $8,855
