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Chestertown Luxury Rentals

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Chestertown Pet Friendly Vacation Rentals

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9.0 (2 Reviews)
House
Basic Adirondack Camp
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
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Chestertown Large Vacation Homes

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10.0 (2 Reviews)
Bed & Breakfast
The Fern Lodge
  • Air Conditioner
  • Parking
  • View
View Availability
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Why Choose Rent By Owner for your Chestertown Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Popular Areas for Chestertown Vacation Rentals

Where are the best neighborhoods to stay in Chestertown?

Exploring the neighborhoods of Chestertown, New York offers a unique opportunity to experience the area's charming atmosphere and natural beauty. Whether you're seeking a peaceful retreat or an active outdoor adventure, staying in this region provides convenient access to local attractions and scenic landscapes. When booking your vacation rentals, consider the distinct neighborhoods that cater to your preferences, ensuring a memorable stay in this welcoming community. With dependable and professional options available, you can enjoy a seamless booking process while discovering the highlights of Chestertown and its surrounding areas.

Friends Lake Inn

Located near the tranquil waters of Friends Lake, this destination offers a serene setting for your getaway and easy access to outdoor activities. You’ll find that staying here provides a peaceful retreat within the region’s natural beauty.

View 129+ Rentals in Friends Lake Inn

Chester Shores

Set along the scenic shoreline, this area is perfect for those seeking waterfront relaxation and recreational opportunities. Here, you can enjoy a tranquil atmosphere while conveniently exploring the attractions of the region.

View 127+ Rentals in Chester Shores

Best Times to Visit Chestertown

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can significantly enhance your experience, with seasonal variations offering unique opportunities to enjoy the region’s natural beauty and local events at their best.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather ideal for outdoor activities and enjoying the natural beauty of this destination.

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

Autumn is a vibrant season here, marked by colorful foliage that attracts visitors seeking scenic views and outdoor adventures.

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

Off-Season Highlights

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Winter (December to February)

The winter months bring colder weather, making it a quieter time for those interested in peaceful retreats and seasonal tranquility.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Spring offers milder temperatures and blooming landscapes, perfect for visitors looking to enjoy the area's renewal without peak crowds.

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

Weekly Weather Forecast for Chestertown

How to Book Your Chestertown 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 Chestertown

More Top-Rated Vacation Rentals in Chestertown Area

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 outdoor seating areas such as patios or decks to relax and take in the scenic views of the area.
  • Take advantage of spacious yards or gardens perfect for outdoor activities or picnics within the region.
  • Benefit from access to private or community fire pits for cozy evenings under the stars.
  • Utilize outdoor grills or barbecue setups ideal for preparing meals while enjoying the fresh air.
  • Explore nearby private docks or waterfront access if the property is situated near lakes or rivers.
  • Make use of well-maintained hiking trails or walking paths often available close to the destination.
  • Capitalize on outdoor recreational equipment like kayaks, paddleboards, or bikes usually offered at properties here.

Top Attractions Around Chestertown

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as hiking, boating, and fishing, all conveniently nearby to enhance your stay in this scenic region.

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Family Activities

  • Kellogg Park: You can enjoy outdoor picnics and family-friendly activities in this scenic park nestled within the region.
  • Indian Lake: Spend a day fishing, boating, or relaxing on the shores of Indian Lake, a popular natural spot for family outings.
  • Adirondack Experience Museum: Discover local history and culture through engaging exhibits that are perfect for curious minds of all ages in the area.
  • Hiking at the Adirondack Mountains: Embark on family-friendly trails that offer stunning views and are suitable for various skill levels here in this mountain region.
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Adult Activities

  • Hiking and Nature Trails: Explore scenic trails around the area to enjoy the natural beauty and serenity that make this destination perfect for outdoor enthusiasts seeking a peaceful retreat.
  • Boating and Water Activities: Spend your days on the water with boating, kayaking, or canoeing, taking advantage of the region’s pristine lakes and rivers.
  • Local Art Galleries and Studios: Discover vibrant art scenes and support local artists by visiting galleries and studios tucked within the area's charming neighborhoods.
  • Historical Site Tours: Immerse yourself in the region’s history by touring notable historical sites that offer insights into the area's rich cultural heritage.

Other Places to Stay in Chestertown, NY

Friends Lake Inn
Friends Lake Inn Vacation Rentals
Loon Lake Beach
Loon Lake Beach Vacation Rentals
Chester Shores
Chester Shores Vacation Rentals
Loon Lake
Loon Lake Vacation Rentals
Friends Lake
Friends Lake Vacation Rentals
Tripp Pond
Tripp Pond Vacation Rentals
More Places to Stay Near Chestertown

Chestertown Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Seasons: Visiting outside peak times allows you to enjoy the tranquility of the region while taking advantage of better rental rates and fewer crowds.
  • Explore Local Outdoor Activities: Take full advantage of the area's natural beauty by engaging in hiking, boating, or fishing for a memorable experience during your stay.
  • Discover Nearby Dining Options: Sampling local cuisine can enhance your trip, so seek out restaurants and cafes that showcase regional flavors within easy reach of your accommodation.
  • Enjoy Personalized Experiences: Consider booking activities or guided tours through trusted providers here to gain unique insights into this destination’s culture and history.

Transportation Options

  • Drive or Rent a Car: Renting a car offers the flexibility to explore the scenic region surrounding your vacation rental in Chestertown at your own pace.
  • Local Bus Services: Bus routes operate within the area, providing an economical and convenient way to reach nearby towns and attractions without hassle.
  • Taxi and Rideshare Services: Taxis and rideshare options are readily available locally, making short trips around this destination straightforward and reliable.
  • Shuttle Services: Airport shuttles and private transfers connect travelers from regional airports directly to their vacation rentals here for added convenience.

Local Customs Options

  • Local Heritage Celebrations: You can participate in regional festivals that honor the area's rich history and community spirit, offering a glimpse into local traditions.
  • Traditional Crafts and Artisanship: Discover the craftsmanship of local artisans through markets and workshops, highlighting the region’s dedication to preserving its cultural heritage.
  • Community Gatherings and Events: Engaging in neighborhood events provides an authentic experience of the area's friendly customs and social bonds.
  • Respect for Natural Surroundings: The local customs emphasize outdoor appreciation and conservation, reflecting the community’s connection to the scenic landscape here.

Frequently Asked Questions About Chestertown?

1. What are the top vacation rentals in Chestertown?

There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestertown:

2. How many vacation rentals have private pools in Chestertown?

There are 1 vacation rentals with private pools near Chestertown. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chestertown are best for families?

If you are looking for a family-friendly vacation home in Chestertown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestertown:

4. How many Rentbyowner vacation rentals are available in Chestertown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 167 in the Chestertown 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 Chestertown. 

5. What is the cancellation policy for a vacation rental in this region?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms and potential fees associated with canceling your reservation.

6. How do I find available vacation rentals for my travel dates in this area?

You can easily search for available properties by entering your desired travel dates on the booking platform, and filter results to match your preferences for location, amenities, and price within the region.

7. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees, such as cleaning charges or service fees, are specified in each listing. Review the booking details carefully or reach out to the property owner for clarification before confirming your reservation.

8. What amenities are typically included in vacation rentals in this destination?

Most vacation rentals nearby include essential amenities like Wi-Fi, kitchen facilities, and parking. However, confirm the specific amenities with the property listing or owner to ensure they meet your needs.

9. Is it possible to communicate directly with property owners before booking in this region?

Yes, the platform allows you to contact property owners directly to ask questions, request additional information, or discuss special arrangements before finalizing your reservation.