Home Vacation Rentals By Owner In Chestertown, NY

Showing 91 Of 91 Vacation Rentals
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Exceptional(14)

$596.63

/ Nightly
Private Vacation Home

Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space

Chestertown, New York, United States

Hot tub with large wraparound deck.great room with fireplace.large kitchen with island.recreation room with bar and pool table sleeps 13,five bedrooms with queen pullout in basement.washer dryer.large dining room
Bed 5

Bed

Bath 2

Bath

Sleep 13

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Exceptional(2)

$588.96

/ Nightly
Private Vacation Home

Start your Adirondack escape at Cape Cotter! Near Gore Mountain and Lake George!

Chestertown, New York, United States

Escape to our Adirondack cape cottage! Sleeps 11 comfortably and is peacefully nestled in the woods, but only 12 miles north of Lake George!br21 miles to Gore Mountain, exit 23 off the Northway. brOnsite parking for Trailers and snowmobiles.brLarge outdoor deck, fire pit. Our home is 0.7 miles from Tripp Lake for fishing and swimming. Non motorized boats are allowed.brCome enjoy this 4 bedroom, 3 full bath Cape style home offering complete privacy for your stay away from Home !
Bed 4

Bed

Bath 3

Bath

Sleep 11

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$367.08

/ Nightly
Cabin

Adirondack Serenity: Pure Escape

Chestertown, New York, United States

Forget your worries in this spacious and serene space. Escape to our secluded Adirondack Mountain Getaway, a stunning new chalet with an open floor plan. Features 3 queen bedrooms, 2 baths, a loft with twin bed, and a galley kitchen with wine fridge, oven, full-size fridge, and dishwasher. Relax on the screen porch, sipping coffee as the wind whistles through the trees. Situated on a dirt road, 4WD/AWD required November to May. Just 35 min to Saratoga horse track, 20 min to Gore Mountain skiing
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(31)

$206.14

/ Nightly
Cottage

Beautiful lakeview cottage on Friends Lake

Chestertown, New York, United States

The cottage is nestled among the pines with a beautiful view of the lake from the front deck. It is rare to find an Adirondack lake with no public access, which is shared with a small home owners association. brThe cottage is very comfortable and set up with all the basic amenities along with cable and Wi-Fi, the only thing you need to bring are your own beach towels and your Adirondack spirit.brCentrally located in the southern Adirondacks it's about a 15 minute drive to the historic village of North Creek, Warrensburg and Cronin's Golf Course and about 30 minutes to Lake George Village, The Painted Pony Rodeo, Six Flags Amusement Park and many other Adirondack activities.brWe look forward to being your Adirondack escape for years to come. brbr*Friends Lake is completely free of invasive species, and in order to keep it that way, we can not allow renters to bring/launch their own boats (This includes; Kayaks, Canoes, Rowboats, Motorized boats of any kind, Paddle Boats, etc.). Thank you for your understanding.* That being said, during your stay there is a rowboat for your private use. Also the owner has two kayaks that you can use during your stay and they are only shared with one other cottage. brbr*Due to the size of the cabin, the owner requests that renters bring no more than 2 dogs*
Bed 2

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Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(3)

$317.24

/ Nightly
Country House

1970s acreage surrounded by trees with deck, grill, & internet

Chestertown, New York, United States

The Stock FarmbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to The Stock Farm – Where Comfort Meets Country CharmbrNestled amid the vibrant hues of the changing seasons, The Stock Farm offers the perfect blend of rustic charm and modern comfort for your next family getaway. Built in 1975 and rich with character, this cozy countryside retreat invites you to create lasting memories in a setting that feels like home—only better.brbrInside, the fully equipped kitchen makes home-cooked meals a breeze, whether you're whipping up breakfast pancakes or grilling burgers on the deck's gas grill while soaking in sweeping views of the surrounding landscape. Thoughtful touches abound, including plush linens, private laundry facilities, and reliable Wi-Fi to keep everyone comfortable and connected.brStep outside and breathe in the fresh country air. Explore the grounds, kick back on the spacious deck, or share stories and s'mores around the glow of the firepit. From peaceful mornings to starlit evenings, The Stock Farm is your family's front-row seat to nature's beauty—with all the comforts of home. Please note: This is a working farm with live animals and caretakers who tend to the livestock. brbrbrWhen you're ready to explore, you'll find that The Stock Farm is perfectly positioned for adventure. Within just 16 miles, you can dive into nature, thrills, and family fun at nearby gems like Friends Lake, the jaw-dropping Natural Stone Bridge & Caves, and the high-flying Adirondack Extreme Adventure Course. Prefer a more relaxed pace Hit the greens at Sagamore Golf Course or carve through the slopes at Gore Mountain Ski Resort, a favorite for winter enthusiasts.brFor a taste of small-town charm, take a short drive to downtown Chestertown. This welcoming community offers local eateries, a nostalgic ice cream parlor, and handy convenience stores—perfect for grabbing that last-minute marshmallow pack before firepit time.brWhether you're chasing thrills or seeking quiet moments, everything you need is just minutes away. brbrThings to KnowbrParts of this home are air-conditioned from approximately Memorial Day until Labor Day each year. This home does not have central air conditioning.brCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(10)

$194.27

/ Nightly
Cabin

Adirondack JEM - 20 Minutes to Lake George or Gore Mountain for Four Season Fun!

Chestertown, New York, United States

Get away from it all this summer and relax with the whole family at this peaceful place to stay in the heart of the Adirondack Park. A great location all year round. 20 minutes from either Lake George or Gore Mountain. Many outdoor activities nearby including the Hiking, Boating, Ausable Chasm, Six Flags and Swimming at our private beach!brbrPlease note that quiet hours start at 10 PM. Excessive noise should be avoided for the benefit of our neighbors and their guests.brbrThe SpacebrA classic Adirondack Cabin in the woods. Our cabin is attached to other homes, you'll walk in to a large open living space with vaulted ceilings and plenty of space for the whole family. The upstairs bedroom includes a full bed and private full bath. The downstairs bedroom includes a twin bunk bed as well as a full bed and an adjoining full bathroom shared with the main space. The kitchen includes everything you'll need to prepare all of your meals which you can enjoy either at the breakfast bar or the dining table.brbrGuest AccessbrGuests will have access to the full space as well as the amenities provided by the Green Mansions Tennis and Swim Club including a private beach on a non-motorized lake as well as Tennis, Pickleball, and Basketball courts. Kayaks and Canoes are available during the summer season and can be signed out for your use.brbrOther Things To NotebrQuiet hours are from 10 PM - 7 AM, we are in a quiet community with other families nearby and your respect of our community will be greatly appreciated.brbrWhile cleaning fees cover general cleaning we do ask that you wash all dishes and run the dishwasher before you leave. We also ask that all used towels are placed in the provided laundry baskets and that everything is in the general location that you found it.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(12)

$178.52

/ Nightly
Cottage

#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

Chestertown, New York, United States

This is a weekly rental (Saturday to Saturday, 7 nights) during the summer season (June 15-Sept 1). Shorter length stays available on the shoulders and off-season (2 night min). Cottages available May 1 till Oct 31. Lodge available all year.brbrLinens, towels, and paper goods NOT provided. Dumpster on property for garbage. Recycling must take to local landfill (pass provided).brbrThe Hillside Retreat cottage at Birchwood Cottages on Loon Lake, Chestertown NY is the smallest of our cottages. It has one bed​room (king bed)​,​ two bath ​rooms, small kitchenette area and living room/dining area with a small flat screen TV. It has a futon ​couch​ and sleeps a total of up to four. This is a great cottage for a couples get away. From the screened in porch that you can see all the action of our property or just take a nap on the day bed. It is a wonderful place to fully enjoy all that the Adirondacks have to offer!brbrWe offer plenty of parking for vehicles, boats and their trailers, cable television, Wi-Fi, campfire pit, and charcoal grill. Swim area with floating dock, deep water to accommodate 25' power boat dock, and sandy beach are available for no additional charge between Memorial Day and Labor Day.brbrEnjoy fishing, swimming, boating and picnicking on beautiful Loon Lake or the many other Adirondack Lakes nearby. Visit Lake George's famous attractions just a short 25 minute drive away. Spend time at neighboring fun spots including Frontier Town, Schroon Lake, Natural Stone Bridge and Caves, Scenic Gore Mountain -- gondola rides, and Ausable Chasm! Horseback riding and golfing are also available nearby!brbrAll well behaved pets are welcome at Birchwood! Small pet fee is extra. We do ask that they remain leashed at all times while on our property. Please pick up after your pets indoors and outdoors. We prefer that they remain downstairs if staying in the Lodge and off the beds/furniture in all units (as to help keep allergens to a minimum).brDue to NYS Department of Health regulations, dogs are not allowed at the beach, in the designated swim area. We do however, have plenty of lakefront shoreline for dogs to enjoy, docks to jump from and some shallow exit areas as well. If you are using Birchwood as a base for a day trip, we ask that you take your pet with you. If that's not possible, we'd be more than happy to recommend a local pet day care. Leaving your pet behind without supervision is not permitted. We don't want them to be frightened or rowdy while you're away -- after all they should enjoy vacation as well.brbrAdditional cottages available on property for the extended family that wants their own space at additional cost. Rec Room is open to all Birchwood guests. brbrYou must provide email address for forwarding of lock box access code, beach waiver, etc. Off VRBO communication is automated and limited. Every reservation requires acknowledgement of receiving and reviewing the Property Rules and Terms of Service.brbrLodge - https://www.vrbo.com/4847591habrCottage #2 - https://www.vrbo.com/7656305habrCottage #3 - https://www.vrbo.com/9160685habrCottage #4 - https://www.vrbo.com/9343827habrCottage #5 - https://www.vrbo.com/7320785habrCottage #6 - https://www.vrbo.com/7320187habrCottage #7 - https://www.vrbo.com/7256241ha
Bed 3

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(25)

$199.8

/ Nightly
Cabin

Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains

Chestertown, New York, United States

Relax in the serene Adirondack Mountains and be close enough to all the activities. The Lakeside at Loon Lake is only 15 minutes from Lake George Village and 15 minutes from the Gore Mountain Ski Area and Mountain Biking Center. We are an affordable, family property located directly across the street from the Loon Lake Public Beach, water fall and boat launch. Our accommodations consist of non-smoking self catering cabins, 2 suites in a duplex and the Loon House (our large main house). Amenities on site are shared: a rowboat, canoe, volleyball, horseshoes, and a play ground for children. All units have their own picnic table & gas grill. The village of Chestertown is two miles from the property. The town has numerous unique shops, , an ice cream parlor, major grocery store, pharmacy, and too many to mention. Within a ten mile radius, you can experience many types of dinning. Self-Catering means we supply your home for your stay while you supply everything else. Sorry, there is no housekeeping during your stay. br
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(6)

$183.15

/ Nightly
Cottage

#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Chestertown, New York, United States

This is a weekly rental (Saturday to Saturday, 7 nights) during the summer season (June 15-Sept 1). Shorter length stays available on the shoulders and off-season (2 night min). Cottages available May 1 till Oct 31. Lodge available all year.brbrLinens, towels and paper goods NOT provided. Garbage to be taken to onsite dumpster. Recycling must be taken to local landfill.brbrThe Chester is a 2 bedroom cottage (2 queen, pull out twin, day bed on porch) and will accommodate 5 people, with 2 small bathrooms – 1 off of each bedroom (with stall showers). Includes a small kitchen, dining and living area. The screened porch and lake views are the perfect way to relax an afternoon away!brbrWe offer plenty of private parking for vehicles, boats and their trailers, cable television, wifi, campfire pit, and charcoal grill. Swim area with floating dock, 25'long deep water boat dock, and sandy beach are available for no additional charge between Memorial Day and Labor Day.brbrEnjoy fishing, swimming, boating and picnicking on beautiful Loon Lake or the many other Adirondack Lakes nearby. Visit Lake George's famous attractions just a short 25 minute drive away. Spend time at neighboring fun spots including Frontier Town, Schroon Lake, Natural Stone Bridge and Caves, Scenic Gore Mountain -- gondola rides, and Ausable Chasm! Horseback riding and golfing are also available nearby!brbrAll well behaved pets are welcome at Birchwood! Small pet fee is extra. We do ask that they remain leashed at all times while on our property. Please pick up after your pets indoors and outdoors. We prefer that they remain downstairs if staying in the Lodge and off the beds/furniture in all units (as to help keep allergens to a minimum).brDue to NYS Department of Health regulations, dogs are not allowed at the beach, in the designated swim area. We do however, have plenty of lakefront shoreline for dogs to enjoy, docks to jump from and some shallow exit areas as well. If you are using Birchwood as a base for a day trip, we ask that you take your pet with you. If that's not possible, we'd be more than happy to recommend a local pet day care. Leaving your pet behind without supervision is not permitted. We don't want them to be frightened or rowdy while you're away -- after all they should enjoy vacation as well.brAdditional cottages available on property for the extended family that wants their own space at additional cost. Rec Room is open to all Birchwood guests. brbrYou must provide email address for forwarding of lock box access code, beach waiver, etc. Off VRBO communication is automated and limited. Every reservation requires acknowledgement of receiving and reviewing the Property Rules and Terms of Service.brbrLodge - https://www.vrbo.com/4847591habrCottage #2 - https://www.vrbo.com/7656305habrCottage #3 - https://www.vrbo.com/9160685habrCottage #4 - https://www.vrbo.com/9343827habrCottage #5 - https://www.vrbo.com/7320785habrCottage #6 - https://www.vrbo.com/7320187habrCottage #7 - https://www.vrbo.com/7256241ha
Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(23)

$323.41

/ Nightly
Condo

Peaceful Lakeside Retreat with Private Beach

Chestertown, New York, United States

Beautiful home on Tripp Lake in the Adirondacks (Lake George Region). Enjoy this pristine property and its lovely grounds which includes a private beach (a short walk from the home), bocce ball court, tennis courts, and golf course. Summers here are great for swimming, kayaking, fishing, and hiking. In the winter, enjoy sledding, snowshoeing or nearby skiing and snowmobiling. This home is conveniently located between Lake George and Gore Mountain. Great restaurants, farmers' markets, festivals, Lake George village, and outlets minutes away. Enjoy all the local attractions and have a peaceful place to come home to.
Bed 3

Bed

Bath 1

Bath

Sleep 5

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Exceptional(10)

$715.95

/ Nightly
Private Vacation Home

Lakefront Home - 20 Min from Gore Mountain w/Hot Tub

Chestertown, New York, United States

Situated directly on beautiful Loon Lake, the Blue Bay Retreat boasts over 200' of lake frontage with a private dock on 5 acres of secluded land. This is the largest lake front property on all of Loon Lake. The Blue Bay Retreat accommodates families of any size w/ 4 bedrooms and 2 full baths. All just minutes to Gore Mtn, Lake George village, and countless other ADK activities!
Bed 4

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Bath 2

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Sleep 10

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Exceptional(10)

$775.89

/ Nightly
Private vacation home

Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW

Chestertown, New York, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(10)

$888.00

/ Nightly
Private vacation home

WaterFront Adirondack Home-located between Gore and Lake George

Chestertown, New York, United States

Bed 4

Bed

Bath 2

Bath

Sleep 14

Sleeps
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Exceptional(10)

$899.10

/ Nightly
Private vacation home

Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.

Chestertown, New York, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

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Exceptional(10)

$302.98

/ Nightly
Private vacation home

NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

Chestertown, New York, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$368.82

/ Nightly
Private vacation home

Year-Round Loon Lake Retreat: Ski, Hike, Explore!

Chestertown, New York, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

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Exceptional(10)

$366.70

/ Nightly
Private vacation home

TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

Chestertown, New York, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

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Exceptional(10)

$357.29

/ Nightly
Private vacation home

4 Mi to Beach & Lake: Spacious Home in Chestertown

Chestertown, New York, United States

Bed 4

Bed

Bath 3

Bath

Sleep 11

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Exceptional(10)

$351.04

/ Nightly
Country House

Historic 1860s Farmhouse, Private Fishing Pond, Canoe, Hot Tub, Walk to Town.

Chestertown, New York, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(10)

$333.00

/ Nightly
Private vacation home

Welcome home!

Chestertown, New York, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(10)

$316.35

/ Nightly
Private vacation home

Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake

Chestertown, New York, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

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