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Chestertown, NY Holiday Rentals, Apartments and Villas
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Chestertown, NY Holiday Rentals, Apartments and Villas
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Distance from
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57 rentals
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Relax at Our River Retreat
35 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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TRIPP LAKE RETREAT, a great place to make Adirondack memories!
67 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
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Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018
47 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Eagles Nest * Loon Lake near Gore Mountain
76 reviews
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 19
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The Roost, a lakefront 4 season home in the Adirondack Mountains
39 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs
23 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Atateka Point Lodge and Treehouse Guest Cottage
15 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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LODGE * BIRCHWOOD COTTAGES AT LOON LAKE. Adirondack Family Friendly Waterfront
28 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
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Green Mansions Vacation Condo
19 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore
40 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region
54 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Tripp Lake Beautiful 4 Season Adirondack Condo Close To Skiing And Lake George
99 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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The Lily Pad at Loon Lake near Gore Mountain
24 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
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Convenient to Gore Mountain. Adjacent to skimobile trail and the' POKER RUN'.
89 reviews
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly
60 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Cozy Home in Private Association on Loon Lake Close to Gore Mountain
16 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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The Treehouse at Atateka Point Lodge
9 reviews
Private Room
2 bedrooms
2 bathrooms
Sleeps 4
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ADK Home near Gore Mountian
24 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom
17 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Loon Lake luxury with beach, kayaks,canoe
19 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck
19 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
21 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Tall Pines On Loon Lake
10 reviews
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
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Lakefront cabin with beautiful loft, game room, views, private dock
18 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Adirondack Getaway at Tripp Lake
19 reviews
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Single-level, spacious house w/ firepit & spacious yard - lake access nearby
25 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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The Chipmunk Cabin, A Beautiful Loon Lake Family Cabin in the Adk Mountains
12 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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A beautiful lake view cabin on Friends Lake
13 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront
5 reviews
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
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Dog-friendly, lakefront house with 2 living areas, beach nearby
12 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Raccoon Retreat, 2 Bedroom 1 Bath Adirondack Cabin, Sleeps Up to 6 People
12 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Beautiful lakeview cottage on Friends Lake
12 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Historic Greek Revival style home w/ screened in porch -near attractions!
8 reviews
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 11
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Lily Pad South at Loon Lake near Gore Mountain
5 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Comfortable year round Lake house on Loon Lake perfect for a getaway
7 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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#4 Loon Lookout * Birchwood Cottages at Loon Lake. Family Friendly Waterfront
4 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Lily Pad North at Loon Lake near Gore Mountain
7 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront
5 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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New listing! Lakefront cabin with beautiful views, lake and beach access
7 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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Cozy cottage with deeded lake rights - 100 steps to the beach
7 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Friends Lake- Quaint and New
3 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
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Lakefront cottage w/ large dock, seasonal firepit, & sandy beach
8 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Family-friendly log cabin with sandy beach, kayaks, near Lake George
4 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
6 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Dog-friendly, lakefront camp cabin w/ a dock & multiple decks
14 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Large, Historic Adirondack Vacation House in ground pool wifi
24 reviews
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 18
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#5 Fireside *Birchwood Cottages at Loon Lake. Family Friendly Waterfront
4 reviews
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
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#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront
2 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!
7 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Dog-friendly cabin with lakefront location, 20' dock, smart TV
13 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
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Frequently Asked Questions about Chestertown
Do any holiday rentals in Chestertown have a pool?
Yes, here are some popular holiday rentals in Chestertown that have a pool:\n
\n
Large, Historic Adirondack Vacation House in ground pool wifi
\n
#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront
\n
#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront
\n
\n
See all holiday rentals with a pool in Chestertown on Tripadvisor
Do any holiday rentals in Chestertown have internet access?
Yes, here are some popular holiday rentals in Chestertown that have internet access:\n
\n
Green Mansions Vacation Condo
\n
Atateka Point Lodge and Treehouse Guest Cottage
\n
The Treehouse at Atateka Point Lodge
\n
\n
See all holiday rentals in Chestertown on Tripadvisor
What are the best pet friendly rentals in Chestertown?
The best pet friendly rentals in Chestertown are:\n
\n
Friends Lake- Quaint and New
\n
Green Mansions Vacation Condo
\n
Atateka Point Lodge and Treehouse Guest Cottage
\n
\n
See all pet friendly holiday rentals in Chestertown on Tripadvisor
What are some great rentals in Chestertown that are kid friendly?
Some of the most popular kid friendly rentals in Chestertown are:\n
\n
Green Mansions Vacation Condo
\n
Atateka Point Lodge and Treehouse Guest Cottage
\n
The Treehouse at Atateka Point Lodge
\n
\n
See all kid friendly holiday rentals in Chestertown on Tripadvisor