Best Vacation Homes in Chestertown
House
10.0(36 Reviews)
2 Bedrooms
1 Bath
8 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
£168/Night
7 Nights - £1,178
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1722.23 ft²
- Fireplace/Heating
Parking
Internet
Child Friendly
£367/Night
7 Nights - £2,569
Bed & Breakfast
10.0(53 Reviews)
1 Bedroom
1 Bath
Hot Tub
Spa- Fireplace/Heating
Ocean View
£343/Night
7 Nights - £2,400
Cottage
10.0(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
946 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£192/Night
7 Nights - £1,341
Bed & Breakfast
10.0(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
508.06 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
View
£392/Night
7 Nights - £2,746
Apartment
9.8(48 Reviews)
2 Bedrooms
1 Bath
5 Guests
893 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£162/Night
7 Nights - £1,131
House
9.8(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£238/Night
7 Nights - £1,665
Cottage
9.6(53 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£170/Night
7 Nights - £1,187
Chestertown Luxury Rentals
Cabin
9.8(16 Reviews)
5 Bedrooms
4 Baths
20 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£904/Night
7 Nights - £6,327
House
9.8(13 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£710/Night
7 Nights - £4,973
House
10.0(43 Reviews)
4 Bedrooms
2 Baths
8 Guests
1512 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£668/Night
7 Nights - £4,676
House
8.4(47 Reviews)
6 Bedrooms
3 Baths
18 Guests
4000 ft²
Private Pool- Fireplace/Heating
Pool- Ocean View
£631/Night
7 Nights - £4,420
House
8.6(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
1422 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£615/Night
7 Nights - £4,304
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
12 Guests
4000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£576/Night
7 Nights - £4,035
House
10.0(15 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£549/Night
7 Nights - £3,845
Cabin
9.8(6 Reviews)
3 Bedrooms
2 Baths
9 Guests
2250 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£538/Night
7 Nights - £3,767
Chestertown Pet Friendly Vacation Rentals
Cottage
9.6(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£153/Night
7 Nights - £1,072
House
9.7(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£314/Night
7 Nights - £2,195
Cabin
9.6(25 Reviews)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£148/Night
7 Nights - £1,039
House
9.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Air Conditioner
£251/Night
7 Nights - £1,756
Cabin
9.4(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£186/Night
7 Nights - £1,299
Cottage
9.4(18 Reviews)
2 Bedrooms
2 Baths
5 Guests
450 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£133/Night
7 Nights - £929
Cottage
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£321/Night
7 Nights - £2,250
House
10.0(106 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£133/Night
7 Nights - £929
Chestertown Large Vacation Homes
House
10.0(115 Reviews)
7 Bedrooms
4 Baths
22 Guests
3229 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£333/Night
7 Nights - £2,332
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
11 Guests
2152.78 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
£192/Night
7 Nights - £1,345
House
10.0(47 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£326/Night
7 Nights - £2,280
House
10.0(1 Review)
1 Bedroom
4 Baths
16 Guests
3304.52 ft²
- View
- Parking
- Air Conditioner
- Internet
£336/Night
7 Nights - £2,354
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£526/Night
7 Nights - £3,685
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£429/Night
7 Nights - £3,003
Cabin
10.0(3 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£404/Night
7 Nights - £2,831
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
£445/Night
7 Nights - £3,114
Why Choose Rent By Owner for your Chestertown 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.
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 117+ Rentals in Friends Lake InnChester 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 125+ Rentals in Chester ShoresBest 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
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
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
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
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
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.
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.
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
Chester Shores
Loon Lake Beach
Friends Lake Inn
Loon Lake
Friends Lake
Tripp Pond
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:
- Eagles Nest at Loon Lake near Gore Mountain
- TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
- Secluded and Cozy Townhome at Tripp Lake
- Loon Lake, Chestertown - spotless, bright chalet for 6-8, close to Public Beach
- Welcome home!
- The Roost, a lakefront 4 season home in the Adirondack Mountains
- The Fern Lodge
- Relax at Our River Retreat
- Rustic Adirondack Retreat on Tripp Lake
- Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
2. 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:
3. How many Rentbyowner vacation rentals are available in Chestertown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 182 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
Chestertown Top Rated Vacation Rentals
Cabin
10.0(42 Reviews)
3 Bedrooms
2 Baths
8 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£257/Night
7 Nights - £1,799
House
10.0(13 Reviews)
4 Bedrooms
2 Baths
8 Guests
900 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£235/Night
7 Nights - £1,645
House
10.0(12 Reviews)
3 Bedrooms
1 Bath
6 Guests
1052 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£294/Night
7 Nights - £2,055
Other
10.0(4 Reviews)
3 Bedrooms
1 Bath
8 Guests
1450 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£276/Night
7 Nights - £1,929
House
9.8(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£286/Night
7 Nights - £2,003
Apartment
9.6(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
1076 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£163/Night
7 Nights - £1,141
Cabin
9.6(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
585 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£228/Night
7 Nights - £1,593
Cabin
9.6(14 Reviews)
3 Bedrooms
1 Bath
6 Guests
726 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£239/Night
7 Nights - £1,674
