1. USA
  2. New York
  3. Lake George
  4. Tripp Pond
  5. Rentals by Owner

Discover Your Perfect Tripp Pond Rentals by Owner

Tripp Pond Rentals by Owner

|
10.0 (2 Reviews)
House
Whit's End
  • Security/Safety
  • Sports/Activities
  • Skiing
View Availability
|
9.5 (2 Reviews)
House
Hideaway Chalet
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Tripp Pond Area

Why Choose Rent By Owner for your Tripp Pond vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Tripp Pond Rentals by Owner

Where are the best neighborhoods to stay in Tripp Pond?

When planning your stay in Tripp Pond, Chestertown, New York, exploring the local neighborhoods can enhance your experience. This charming area offers a variety of rental options near serene natural settings and quiet residential streets, making it ideal for those seeking a peaceful retreat. Whether you're interested in waterfront properties or cozy retreats nestled within the community, you'll find that each neighborhood provides easy access to the scenic beauty and outdoor activities that define the region. Booking your vacation rental through Rent By Owner ensures a reliable and straightforward process, helping you discover the perfect home away from home in this picturesque part of New York.

Friends Lake Inn

Located near the tranquil waters of Friends Lake, this inn offers a peaceful retreat perfect for exploring the natural beauty of the area. You can enjoy a cozy stay while being close to the region's scenic outdoor activities.

View 129+ Rentals in Friends Lake Inn

Chester Shores

Situated along the serene Chester Shores, this neighborhood provides easy access to relaxing waterfront views and outdoor pursuits. It’s an ideal spot for those seeking a tranquil environment within reach of local attractions.

View 127+ Rentals in Chester Shores

Best Times to Visit Tripp Pond

When should you plan your Rentals by Owner stay?

Choosing the ideal time to plan your stay here ensures you can enjoy all that this destination has to offer within the region’s pleasant climate and seasonal charm, making your rental experience both memorable and hassle-free.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities in the area.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

The early fall offers mild temperatures and vibrant foliage, creating a picturesque backdrop for your stay in this region.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

image
Winter (December to February)

In winter, the area transforms into a peaceful retreat for those seeking solitude or winter sports opportunities nearby.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
image
Spring (March to May)

Springtime brings a quiet charm with blooming flora and gradually rising temperatures, perfect for a serene getaway.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Tripp Pond

How to Book Your Tripp Pond vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Tripp Pond

More Top-Rated Rentals by Owner in Tripp Pond Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 seating area perfect for relaxing and dining while immersed in the natural beauty of the region.
  • Take advantage of a spacious yard ideal for outdoor games, picnics, or simply soaking up the sunshine.
  • Make the most of a lakeside dock or boat slip, offering easy access for boating, fishing, or enjoying tranquil water views.
  • Utilize on-site barbecue grills to enhance your outdoor meals in this scenic setting.
  • Relax on a hammock or lounge chairs set up amidst lush surroundings for ultimate outdoor leisure.
  • Discover well-maintained hiking trails or pathways nearby for outdoor exploration and adventure.
  • Benefit from ample parking space suited for boats, RVs, or additional vehicles during your stay.

Top Attractions Around Tripp Pond

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities such as boating, fishing, and hiking, all within close proximity to your rental by owner experience in Tripp Pond, Chestertown, New York, USA.

image
image

Family Activities

  • Fishing at Tripp Pond: Enjoy a relaxing day casting your line in the pristine waters, which are perfect for families seeking a peaceful outdoor adventure.
  • Hiking Trails in the Region: Explore scenic trails nearby, offering stunning views and opportunities for family-friendly walks in this picturesque area.
  • Swimming and Water Activities: Take advantage of the calm waters to go swimming or participate in water-based fun suitable for all ages here at Tripp Pond.
  • Picnicking by the Water: Pack a picnic and unwind with your loved ones along the shoreline, enjoying the natural beauty that surrounds this destination.
image

Adult Activities

  • Fishing at Tripp Pond: Enjoy a relaxing day casting your line in the tranquil waters of this popular local spot, perfect for anglers seeking a peaceful retreat.
  • Hiking and Nature Walking: Explore scenic trails nearby that wind through lush landscapes, offering stunning views and an immersive outdoor experience in the area.
  • Boating and Kayaking: Take advantage of the calm waters with a boat or kayak rental to discover the region from a unique perspective on the water.
  • Wildlife Observation: Visit natural areas around here where you can observe local fauna and enjoy birdwatching amidst the quiet surroundings.

Tripp Pond Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Nearby Activities: Research local outdoor activities and amenities to maximize your time exploring the natural beauty of the area around Tripp Pond.
  • Communicate with Your Host: Engage with your rental owner to receive insider tips and ensure a smooth stay in this tranquil destination.
  • Pack Appropriately for the Climate: Prepare for varying weather conditions in the region to make your outdoor adventures more comfortable and enjoyable.
  • Utilize Local Resources: Take advantage of nearby maps, brochures, and guides provided by your host or available locally to uncover hidden gems in the vicinity.

Transportation Options

  • Car Rental Services: You can access reliable car rental agencies in the area, offering convenient transportation options for exploring Chestertown and its surrounding region.
  • Taxi and Rideshare Services: Taxis and rideshare providers like Uber and Lyft are available locally, providing flexible travel around the destination without the need for personal vehicle ownership.
  • Public Transportation: Local bus services offer an affordable way to navigate the area, connecting you to key points of interest and nearby towns with ease.
  • Bike Rentals: Biking is a popular option here, with several bike rental shops providing equipment for exploring the scenic surroundings at your own pace.

Local Customs Options

  • Respect for Nature: Locals in the area cherish their surrounding natural environment, often practicing responsible outdoor activities and conservation efforts.
  • Community Traditions: Community gatherings and local festivals are common here, offering a glimpse into the region’s rich heritage and shared customs.
  • Outdoor Etiquette: When enjoying the lakeside or forest areas, it is customary to follow stewardship principles like Leave No Trace to preserve the area's pristine beauty.
  • Local Hospitality: Visitors can expect warm welcomes and friendly interactions, as communal hospitality remains an integral part of this destination’s character.

Frequently Asked Questions About Tripp Pond Rentals by Owner

1. What are the top vacation rentals in Tripp Pond?

There are a lot of options in Tripp Pond. If you plan on staying in the Tripp 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 Tripp Pond:

2. How many Rentbyowner vacation rentals are available in Tripp Pond?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 45 in the Tripp 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 Tripp Pond. 

3. What is the cancellation policy for a rental by owner in Tripp Pond, Chestertown?

The cancellation policy varies depending on the specific listing. You should review the rental's cancellation terms on the listing page or contact the owner directly for detailed information.

4. How do I confirm my booking with a rental owner in this area?

Booking confirmation typically occurs after you complete the reservation process and receive a confirmation email from the owner or the rental platform. Be sure to read all details and communicate with the owner if needed.

5. Are there any additional fees to be aware of when booking a rental here?

Additional fees such as cleaning, security deposits, or service charges may apply. These will be clearly listed on the rental’s page, but it’s best to verify with the host before finalizing your reservation.

6. What amenities are usually included in a rental by owner around here?

Most rentals include basic amenities such as Wi-Fi, kitchen facilities, and linens. For specific features like outdoor spaces or special equipment, refer to the individual listing details or contact the owner directly.

7. How do I contact the owner if I have questions about my stay in this region?

You can reach out to the owner through the messaging system on the booking platform. It's recommended to clarify any concerns or special requests before completing your reservation to ensure a smooth stay.

More Rentals You May Like Near Tripp Pond

More Top-Rated Rentals by Owner in Tripp Pond Area