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Chestertown Holiday Apartments

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57 rentals in Chestertown.
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Relax at Our River Retreat, holiday rental in Chestertown
Relax at Our River Retreat, holiday rental in Chestertown
Relax at Our River Retreat, holiday rental in Chestertown

Relax at Our River Retreat

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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TRIPP LAKE RETREAT, a great place to make Adirondack memories!, holiday rental in Chestertown
TRIPP LAKE RETREAT, a great place to make Adirondack memories!, holiday rental in Chestertown
TRIPP LAKE RETREAT, a great place to make Adirondack memories!, holiday rental in Chestertown

TRIPP LAKE RETREAT, a great place to make Adirondack memories!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018, holiday rental in Chestertown
Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018, holiday rental in Chestertown
Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018, holiday rental in Chestertown

Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Eagles Nest * Loon Lake near Gore Mountain, holiday rental in Chestertown
Eagles Nest * Loon Lake near Gore Mountain, holiday rental in Chestertown
Eagles Nest * Loon Lake near Gore Mountain, holiday rental in Chestertown

Eagles Nest * Loon Lake near Gore Mountain

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 19
Match: Sleeps
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The Roost, a lakefront 4 season home in the Adirondack Mountains, holiday rental in Chestertown
The Roost, a lakefront 4 season home in the Adirondack Mountains, holiday rental in Chestertown
The Roost, a lakefront 4 season home in the Adirondack Mountains, holiday rental in Chestertown

The Roost, a lakefront 4 season home in the Adirondack Mountains

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs, holiday rental in Chestertown
Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs, holiday rental in Chestertown
Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs, holiday rental in Chestertown

Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Atateka Point Lodge and Treehouse Guest Cottage, holiday rental in Chestertown
Atateka Point Lodge and Treehouse Guest Cottage, holiday rental in Chestertown
Atateka Point Lodge and Treehouse Guest Cottage, holiday rental in Chestertown

Atateka Point Lodge and Treehouse Guest Cottage

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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LODGE * BIRCHWOOD COTTAGES AT LOON LAKE. Adirondack Family Friendly Waterfront

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Green Mansions Vacation Condo, holiday rental in Chestertown
Green Mansions Vacation Condo, holiday rental in Chestertown
Green Mansions Vacation Condo, holiday rental in Chestertown

Green Mansions Vacation Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, holiday rental in Chestertown
Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, holiday rental in Chestertown
Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, holiday rental in Chestertown

Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region, holiday rental in Chestertown
Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region, holiday rental in Chestertown
Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region, holiday rental in Chestertown

Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, holiday rental in Chestertown
Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, holiday rental in Chestertown
Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, holiday rental in Chestertown

Tripp Lake Beautiful 4 Season Adirondack Condo Close To Skiing And Lake George

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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The Lily Pad at Loon Lake near Gore Mountain, holiday rental in Chestertown
The Lily Pad at Loon Lake near Gore Mountain, holiday rental in Chestertown
The Lily Pad at Loon Lake near Gore Mountain, holiday rental in Chestertown

The Lily Pad at Loon Lake near Gore Mountain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., holiday rental in Chestertown
Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., holiday rental in Chestertown
Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., holiday rental in Chestertown

Convenient to Gore Mountain. Adjacent to skimobile trail and the' POKER RUN'.

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, holiday rental in Chestertown
Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, holiday rental in Chestertown
Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, holiday rental in Chestertown

Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Home in Private Association on Loon Lake
Close to Gore Mountain, holiday rental in Chestertown
Cozy Home in Private Association on Loon Lake
Close to Gore Mountain, holiday rental in Chestertown
Cozy Home in Private Association on Loon Lake
Close to Gore Mountain, holiday rental in Chestertown

Cozy Home in Private Association on Loon Lake Close to Gore Mountain

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Treehouse at Atateka Point  Lodge, holiday rental in Chestertown
The Treehouse at Atateka Point  Lodge, holiday rental in Chestertown
The Treehouse at Atateka Point  Lodge, holiday rental in Chestertown

The Treehouse at Atateka Point Lodge

Private Room
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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ADK Home near Gore Mountian, holiday rental in Chestertown
ADK Home near Gore Mountian, holiday rental in Chestertown
ADK Home near Gore Mountian, holiday rental in Chestertown

ADK Home near Gore Mountian

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, holiday rental in Chestertown
Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, holiday rental in Chestertown
Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, holiday rental in Chestertown

Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Loon Lake luxury with beach, kayaks,canoe, holiday rental in Chestertown
Loon Lake luxury with beach, kayaks,canoe, holiday rental in Chestertown
Loon Lake luxury with beach, kayaks,canoe, holiday rental in Chestertown

Loon Lake luxury with beach, kayaks,canoe

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, holiday rental in Chestertown
Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, holiday rental in Chestertown
Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, holiday rental in Chestertown

Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tall Pines On Loon Lake, holiday rental in Chestertown
Tall Pines On Loon Lake, holiday rental in Chestertown
Tall Pines On Loon Lake, holiday rental in Chestertown

Tall Pines On Loon Lake

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lakefront cabin with beautiful loft, game room, views, private dock, holiday rental in Chestertown
Lakefront cabin with beautiful loft, game room, views, private dock, holiday rental in Chestertown
Lakefront cabin with beautiful loft, game room, views, private dock, holiday rental in Chestertown

Lakefront cabin with beautiful loft, game room, views, private dock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Adirondack Getaway at Tripp Lake, holiday rental in Chestertown
Adirondack Getaway at Tripp Lake, holiday rental in Chestertown
Adirondack Getaway at Tripp Lake, holiday rental in Chestertown

Adirondack Getaway at Tripp Lake

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Single-level, spacious house w/ firepit & spacious yard - lake access nearby, holiday rental in Chestertown
Single-level, spacious house w/ firepit & spacious yard - lake access nearby, holiday rental in Chestertown
Single-level, spacious house w/ firepit & spacious yard - lake access nearby, holiday rental in Chestertown

Single-level, spacious house w/ firepit & spacious yard - lake access nearby

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Chipmunk Cabin, A Beautiful Loon Lake Family Cabin in the Adk Mountains, holiday rental in Chestertown
The Chipmunk Cabin, A Beautiful Loon Lake Family Cabin in the Adk Mountains, holiday rental in Chestertown
The Chipmunk Cabin, A Beautiful Loon Lake Family Cabin in the Adk Mountains, holiday rental in Chestertown

The Chipmunk Cabin, A Beautiful Loon Lake Family Cabin in the Adk Mountains

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A beautiful lake view cabin on Friends Lake, holiday rental in Chestertown
A beautiful lake view cabin on Friends Lake, holiday rental in Chestertown
A beautiful lake view cabin on Friends Lake, holiday rental in Chestertown

A beautiful lake view cabin on Friends Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown

#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dog-friendly, lakefront house with 2 living areas, beach nearby, holiday rental in Chestertown
Dog-friendly, lakefront house with 2 living areas, beach nearby, holiday rental in Chestertown
Dog-friendly, lakefront house with 2 living areas, beach nearby, holiday rental in Chestertown

Dog-friendly, lakefront house with 2 living areas, beach nearby

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Raccoon Retreat, 2 Bedroom 1 Bath Adirondack Cabin, Sleeps Up to 6 People, holiday rental in Chestertown
Raccoon Retreat, 2 Bedroom 1 Bath Adirondack Cabin, Sleeps Up to 6 People, holiday rental in Chestertown
Raccoon Retreat, 2 Bedroom 1 Bath Adirondack Cabin, Sleeps Up to 6 People, holiday rental in Chestertown

Raccoon Retreat, 2 Bedroom 1 Bath Adirondack Cabin, Sleeps Up to 6 People

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful lakeview cottage on Friends Lake, holiday rental in Chestertown
Beautiful lakeview cottage on Friends Lake, holiday rental in Chestertown
Beautiful lakeview cottage on Friends Lake, holiday rental in Chestertown

Beautiful lakeview cottage on Friends Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Greek Revival style home w/ screened in porch -near attractions!, holiday rental in Chestertown
Historic Greek Revival style home w/ screened in porch -near attractions!, holiday rental in Chestertown
Historic Greek Revival style home w/ screened in porch -near attractions!, holiday rental in Chestertown

Historic Greek Revival style home w/ screened in porch -near attractions!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Lily Pad South at Loon Lake near Gore Mountain, holiday rental in Chestertown
Lily Pad South at Loon Lake near Gore Mountain, holiday rental in Chestertown
Lily Pad South at Loon Lake near Gore Mountain, holiday rental in Chestertown

Lily Pad South at Loon Lake near Gore Mountain

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Comfortable year round Lake house on Loon Lake perfect for a getaway, holiday rental in Chestertown
Comfortable year round Lake house on Loon Lake perfect for a getaway, holiday rental in Chestertown
Comfortable year round Lake house on Loon Lake perfect for a getaway, holiday rental in Chestertown

Comfortable year round Lake house on Loon Lake perfect for a getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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#4 Loon Lookout * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#4 Loon Lookout * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#4 Loon Lookout * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown

#4 Loon Lookout * Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lily Pad North at Loon Lake near Gore Mountain, holiday rental in Chestertown
Lily Pad North at Loon Lake near Gore Mountain, holiday rental in Chestertown
Lily Pad North at Loon Lake near Gore Mountain, holiday rental in Chestertown

Lily Pad North at Loon Lake near Gore Mountain

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown

#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New listing! Lakefront cabin with beautiful views, lake and beach access, holiday rental in Chestertown
New listing! Lakefront cabin with beautiful views, lake and beach access, holiday rental in Chestertown
New listing! Lakefront cabin with beautiful views, lake and beach access, holiday rental in Chestertown

New listing! Lakefront cabin with beautiful views, lake and beach access

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Cozy cottage with deeded lake rights - 100 steps to the beach, holiday rental in Chestertown
Cozy cottage with deeded lake rights - 100 steps to the beach, holiday rental in Chestertown
Cozy cottage with deeded lake rights - 100 steps to the beach, holiday rental in Chestertown

Cozy cottage with deeded lake rights - 100 steps to the beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Friends Lake- Quaint and New, holiday rental in Chestertown
Friends Lake- Quaint and New, holiday rental in Chestertown
Friends Lake- Quaint and New, holiday rental in Chestertown

Friends Lake- Quaint and New

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront cottage w/ large dock, seasonal firepit, & sandy beach, holiday rental in Chestertown
Lakefront cottage w/ large dock, seasonal firepit, & sandy beach, holiday rental in Chestertown
Lakefront cottage w/ large dock, seasonal firepit, & sandy beach, holiday rental in Chestertown

Lakefront cottage w/ large dock, seasonal firepit, & sandy beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family-friendly log cabin with sandy beach, kayaks, near Lake George, holiday rental in Chestertown
Family-friendly log cabin with sandy beach, kayaks, near Lake George, holiday rental in Chestertown
Family-friendly log cabin with sandy beach, kayaks, near Lake George, holiday rental in Chestertown

Family-friendly log cabin with sandy beach, kayaks, near Lake George

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, holiday rental in Chestertown

Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, holiday rental in Chestertown
Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, holiday rental in Chestertown
Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, holiday rental in Chestertown

Dog-friendly, lakefront camp cabin w/ a dock & multiple decks

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large, Historic Adirondack Vacation House in ground pool wifi, holiday rental in Chestertown
Large, Historic Adirondack Vacation House in ground pool wifi, holiday rental in Chestertown
Large, Historic Adirondack Vacation House in ground pool wifi, holiday rental in Chestertown

Large, Historic Adirondack Vacation House in ground pool wifi

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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#5 Fireside *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#5 Fireside *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#5 Fireside *Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown

#5 Fireside *Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown
#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront, holiday rental in Chestertown

#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, holiday rental in Chestertown
Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, holiday rental in Chestertown
Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, holiday rental in Chestertown

Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dog-friendly cabin with lakefront location, 20' dock, smart TV, holiday rental in Chestertown
Dog-friendly cabin with lakefront location, 20' dock, smart TV, holiday rental in Chestertown
Dog-friendly cabin with lakefront location, 20' dock, smart TV, holiday rental in Chestertown

Dog-friendly cabin with lakefront location, 20' dock, smart TV

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Chestertown