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- Maryland
- Still Pond
- Rentals by Owner
Discover Your Ideal Still Pond, Maryland Rental by Owner for a Relaxing Getaway
Discover Your Perfect Still Pond Rentals by Owner
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Rentals by Owner
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Luxury Vacation Rentals
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Still Pond Rentals by Owner
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Parking
- Accessibility
- Security/Safety
- Air Conditioner
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- TV
Why Choose Rent By Owner for your Still Pond vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Still Pond
When should you plan your Rentals by Owner stay?
Timing your vacation here can enhance your experience, so consider visiting during the region's most pleasant seasons to enjoy optimal weather and local events when you book your rental by owner through Rent By Owner in Still Pond, Maryland.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences its peak visitation period, making it ideal for outdoor activities and enjoying the region's natural beauty.
Fall (September to November)
Autumn is a popular time to visit, as the area's scenic landscapes are transformed with vibrant fall foliage, attracting travelers seeking picturesque scenery and calm retreats.
Off-Season Highlights
Winter (December to February)
In the colder months, fewer visitors come here, offering a quieter experience and an opportunity to enjoy the peaceful, off-season charm of the region.
Early Spring (March to April)
Before the full bloom, early spring sees fewer travelers, providing a more relaxed environment and a chance to appreciate the area's emerging natural beauty.
Weekly Weather Forecast for Still Pond
How to Book Your Still Pond vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Still Pond
Common Rentals by Owner Amenities
What amenities can you expect?
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
- You can enjoy spacious outdoor patios or decks, perfect for relaxing or entertaining in the region's pleasant climate.
- Many rentals feature private gardens or lush lawns where you can unwind amidst natural beauty.
- Expect to find access to scenic walking trails or nature paths that showcase the area's picturesque landscape.
- Some properties offer outdoor dining areas, ideal for enjoying meals while taking in the fresh air of this charming destination.
- Look for rentals with swimming pools or hot tubs to enhance your outdoor experience in the region’s inviting atmosphere.
- Outdoor fire pits are commonly available, providing a cozy setting for evening gatherings under the stars.
- Convenient parking spaces or drive-up access make exploring the outskirts of this destination easy and hassle-free.
Top Attractions Around Still Pond
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities and scenic explorations that showcase the natural beauty of the region, making it an ideal destination for those seeking relaxation and adventure during their stay.

Family Activities
- Still Pond Community Park: Enjoy a family picnic or play games on the open fields, making it an ideal outdoor activity spot in the area.
- Fishing at Still Pond: Spend a relaxing day casting lines in the calm waters, perfect for introducing kids to freshwater fishing in this peaceful region.
- Nature Trails around Still Pond: Explore scenic walking and biking paths that wind through the local landscape, offering opportunities for outdoor adventure with your loved ones.
- Boat Rentals on the Chesapeake Bay: Experience the region from the water by renting boats nearby, providing memorable outings for the whole family in this charming destination.
Adult Activities
- Boating and Fishing on Still Pond: Enjoy a relaxing day on the water by renting a boat or fishing gear to explore the tranquil waters of the area.
- Visit Chesapeake Bay Maritime Museum: Discover the region's rich maritime history through captivating exhibits and interactive displays right in this scenic destination.
- Nature Exploration at Still Pond Nature Reserve: Immerse yourself in the natural beauty of the region with serene walks and birdwatching opportunities within the preserve.
- Explore Local Eateries and Farmers Markets: Savor fresh, regional cuisine and support local vendors at nearby markets, offering an authentic taste of the area’s flavors.
Still Pond Travel Tips
How Can You Make the Most of Your Stay?
- Explore local natural sights: Take advantage of the area's scenic beauty by visiting nearby parks and waterfronts to experience the region's outdoor charm firsthand.
- Connect with community events: Engage in seasonal festivals or local markets to immerse yourself in the local culture and meet fellow visitors and residents.
- Plan your activities ahead: Research popular spots and hidden gems within the region to create a tailored itinerary that maximizes your stay.
- Choose rental by owner accommodations: Opt for trusted, owner-managed rentals to enjoy personalized service and a more authentic experience here.
Transportation Options
- Car Rentals: Renting a car here provides you with the flexibility to explore the scenic region and its charming surroundings at your own pace.
- Local Taxis and Rideshare Services: These transportation options are readily available for quick trips within the area, offering convenient access to nearby attractions.
- Public Transit: Bus services in the region connect you to key destinations, making it easier to navigate without the need for a private vehicle.
- Bicycle Rentals: Given the area's peaceful environment, cycling offers an eco-friendly way to enjoy the natural beauty of this part of Maryland.
Local Customs Options
- Tranquil Waterway Etiquette: Respect for the region’s serene waterways is essential, so ensure proper boating and fishing practices to preserve its natural beauty.
- Local Seafood Traditions: The area takes pride in its fresh seafood, and supporting local vendors by enjoying regional specialties helps uphold this customary culinary practice.
- Historic Preservation Respect: Respect for historical sites and landmarks here reflects the community’s dedication to maintaining its charming heritage.
- Community Event Participation: Engaging in neighborhood gatherings and seasonal festivals showcases the welcoming spirit of this destination and its residents.
Frequently Asked Questions About Still Pond Rentals by Owner
1. What are the top vacation rentals in Still Pond?
There are a lot of options in Still Pond. If you plan on staying in the Still Pond area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Still Pond:
- Chesapeake Bay Waterfront Cottage. Comforts of home with unobstructed water view
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Eastern Shore Get Away
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- Contemporary waterfront house with private dock & kayaks!
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Historic Downtown Garden Oasis with Private Patio
2. How many Rentbyowner vacation rentals are available in Still Pond?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 91 in the Still Pond 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 Still Pond.
3. What is the cancellation policy for rental properties by owner in Still Pond, Maryland?
4. How do I communicate with the property owner when booking a rental in Still Pond?
5. Are there any additional fees associated with renting directly from an owner in this area?
6. What amenities are typically included in rental by owner properties in the region?
7. Is it safe to book a vacation rental by owner in Still Pond, Maryland through Rent By Owner?
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