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Chestertown Vacation Rentals

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85 rentals in Chestertown.
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Eagles Nest * Loon Lake near Gore Mountain, vacation rental in Chestertown
Eagles Nest * Loon Lake near Gore Mountain, vacation rental in Chestertown
Eagles Nest * Loon Lake near Gore Mountain, vacation rental in Chestertown

Eagles Nest * Loon Lake near Gore Mountain

Rental Home
7 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Relax at Our River Retreat, vacation rental in Chestertown
Relax at Our River Retreat, vacation rental in Chestertown
Relax at Our River Retreat, vacation rental in Chestertown

Relax at Our River Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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TRIPP LAKE RETREAT, a great place to make Adirondack memories!, vacation rental in Chestertown
TRIPP LAKE RETREAT, a great place to make Adirondack memories!, vacation rental in Chestertown
TRIPP LAKE RETREAT, a great place to make Adirondack memories!, vacation rental in Chestertown

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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The Roost, a lakefront 4 season home in the Adirondack Mountains, vacation rental in Chestertown
The Roost, a lakefront 4 season home in the Adirondack Mountains, vacation rental in Chestertown
The Roost, a lakefront 4 season home in the Adirondack Mountains, vacation rental in Chestertown

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore, vacation rental in Chestertown
Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore, vacation rental in Chestertown
Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore, vacation rental in Chestertown

Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Atateka Point Lodge and Treehouse Guest Cottage, vacation rental in Chestertown
Atateka Point Lodge and Treehouse Guest Cottage, vacation rental in Chestertown
Atateka Point Lodge and Treehouse Guest Cottage, vacation rental in Chestertown

Atateka Point Lodge and Treehouse Guest Cottage

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Lily Pad at Loon Lake near Gore Mountain, vacation rental in Chestertown
The Lily Pad at Loon Lake near Gore Mountain, vacation rental in Chestertown
The Lily Pad at Loon Lake near Gore Mountain, vacation rental in Chestertown

The Lily Pad at Loon Lake near Gore Mountain

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Green Mansions Vacation Condo, vacation rental in Chestertown
Green Mansions Vacation Condo, vacation rental in Chestertown
Green Mansions Vacation Condo, vacation rental in Chestertown

Green Mansions Vacation Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, vacation rental in Chestertown
Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, vacation rental in Chestertown
Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly, vacation 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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Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, vacation rental in Chestertown
Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, vacation rental in Chestertown
Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck, vacation rental in Chestertown

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, vacation rental in Chestertown
Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, vacation rental in Chestertown
Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George, vacation 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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ADK Home near Gore Mountian, vacation rental in Chestertown
ADK Home near Gore Mountian, vacation rental in Chestertown
ADK Home near Gore Mountian, vacation rental in Chestertown

ADK Home near Gore Mountian

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, vacation rental in Chestertown
Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, vacation rental in Chestertown
Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore, vacation 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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Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, vacation rental in Chestertown
Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, vacation rental in Chestertown
Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom, vacation rental in Chestertown

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Treehouse at Atateka Point  Lodge, vacation rental in Chestertown
The Treehouse at Atateka Point  Lodge, vacation rental in Chestertown
The Treehouse at Atateka Point  Lodge, vacation rental in Chestertown

The Treehouse at Atateka Point Lodge

Private Room
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Loon Lake luxury with beach, kayaks,canoe, vacation rental in Chestertown
Loon Lake luxury with beach, kayaks,canoe, vacation rental in Chestertown
Loon Lake luxury with beach, kayaks,canoe, vacation rental in Chestertown

Loon Lake luxury with beach, kayaks,canoe

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., vacation rental in Chestertown
Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., vacation rental in Chestertown
Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'., vacation rental in Chestertown

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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A beautiful lake view cabin on Friends Lake, vacation rental in Chestertown
A beautiful lake view cabin on Friends Lake, vacation rental in Chestertown
A beautiful lake view cabin on Friends Lake, vacation rental in Chestertown

A beautiful lake view cabin on Friends Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Winter on Loon Lake, Hot tub, ski Gore, snowmobile, vacation rental in Chestertown
Winter on Loon Lake, Hot tub, ski Gore, snowmobile, vacation rental in Chestertown
Winter on Loon Lake, Hot tub, ski Gore, snowmobile, vacation rental in Chestertown

Winter on Loon Lake, Hot tub, ski Gore, snowmobile

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue Loon Retreat-Near Gore-Cozy Home-Private Loon Lake Access, vacation rental in Chestertown
Blue Loon Retreat-Near Gore-Cozy Home-Private Loon Lake Access, vacation rental in Chestertown
Blue Loon Retreat-Near Gore-Cozy Home-Private Loon Lake Access, vacation rental in Chestertown

Blue Loon Retreat-Near Gore-Cozy Home-Private Loon Lake Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront home steps away from sandy beach & fire pit - close to hiking & skiing, vacation rental in Chestertown
Lakefront home steps away from sandy beach & fire pit - close to hiking & skiing, vacation rental in Chestertown
Lakefront home steps away from sandy beach & fire pit - close to hiking & skiing, vacation rental in Chestertown

Lakefront home steps away from sandy beach & fire pit - close to hiking & skiing

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tall Pines On Loon Lake, vacation rental in Chestertown
Tall Pines On Loon Lake, vacation rental in Chestertown
Tall Pines On Loon Lake, vacation rental in Chestertown

Tall Pines On Loon Lake

Rental Home
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adirondack Getaway at Tripp Lake, vacation rental in Chestertown
Adirondack Getaway at Tripp Lake, vacation rental in Chestertown
Adirondack Getaway at Tripp Lake, vacation rental in Chestertown

Adirondack Getaway at Tripp Lake

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lakefront cabin with beautiful loft, game room, views, private dock, vacation rental in Chestertown
Lakefront cabin with beautiful loft, game room, views, private dock, vacation rental in Chestertown
Lakefront cabin with beautiful loft, game room, views, private dock, vacation rental in Chestertown

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Comfortable year round Lake house on Loon Lake perfect for a getaway, vacation rental in Chestertown
Comfortable year round Lake house on Loon Lake perfect for a getaway, vacation rental in Chestertown
Comfortable year round Lake house on Loon Lake perfect for a getaway, vacation rental in Chestertown

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly, lakefront house with 2 living areas, beach nearby, vacation rental in Chestertown
Dog-friendly, lakefront house with 2 living areas, beach nearby, vacation rental in Chestertown
Dog-friendly, lakefront house with 2 living areas, beach nearby, vacation rental in Chestertown

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Lake Front House with Amazing Views on Loon Lake, vacation rental in Chestertown
Private Lake Front House with Amazing Views on Loon Lake, vacation rental in Chestertown
Private Lake Front House with Amazing Views on Loon Lake, vacation rental in Chestertown

Private Lake Front House with Amazing Views on Loon Lake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2, vacation rental in Chestertown
Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2, vacation rental in Chestertown
Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2, vacation rental in Chestertown

Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Greek Revival style home w/ screened in porch -near attractions!, vacation rental in Chestertown
Historic Greek Revival style home w/ screened in porch -near attractions!, vacation rental in Chestertown
Historic Greek Revival style home w/ screened in porch -near attractions!, vacation rental in Chestertown

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful lakeview cottage on Friends Lake, vacation rental in Chestertown
Beautiful lakeview cottage on Friends Lake, vacation rental in Chestertown
Beautiful lakeview cottage on Friends Lake, vacation rental in Chestertown

Beautiful lakeview cottage on Friends Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Raccoon Retreat, 2 Bedroom 1 Bath Cabin, Sleeps Up to 6 People, vacation rental in Chestertown
Raccoon Retreat, 2 Bedroom 1 Bath Cabin, Sleeps Up to 6 People, vacation rental in Chestertown
Raccoon Retreat, 2 Bedroom 1 Bath Cabin, Sleeps Up to 6 People, vacation rental in Chestertown

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

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

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Summer Vibes | Lake George | Hot Tub | Fire pit, vacation rental in Chestertown
Summer Vibes | Lake George | Hot Tub | Fire pit, vacation rental in Chestertown
Summer Vibes | Lake George | Hot Tub | Fire pit, vacation rental in Chestertown

Summer Vibes | Lake George | Hot Tub | Fire pit

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Single-level, spacious house w/ firepit & spacious yard - lake access nearby, vacation rental in Chestertown
Single-level, spacious house w/ firepit & spacious yard - lake access nearby, vacation rental in Chestertown
Single-level, spacious house w/ firepit & spacious yard - lake access nearby, vacation rental in Chestertown

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lily Pad South at Loon Lake near Gore Mountain, vacation rental in Chestertown
Lily Pad South at Loon Lake near Gore Mountain, vacation rental in Chestertown
Lily Pad South at Loon Lake near Gore Mountain, vacation 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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Cozy cottage with deeded lake rights - 100 steps to the beach, vacation rental in Chestertown
Cozy cottage with deeded lake rights - 100 steps to the beach, vacation rental in Chestertown
Cozy cottage with deeded lake rights - 100 steps to the beach, vacation rental in Chestertown

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains, vacation rental in Chestertown

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lily Pad North at Loon Lake near Gore Mountain, vacation rental in Chestertown
Lily Pad North at Loon Lake near Gore Mountain, vacation rental in Chestertown
Lily Pad North at Loon Lake near Gore Mountain, vacation 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 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Elizabeth. A Guest House Near Lake George., vacation rental in Chestertown
Elizabeth. A Guest House Near Lake George., vacation rental in Chestertown
Elizabeth. A Guest House Near Lake George., vacation rental in Chestertown

Elizabeth. A Guest House Near Lake George.

Rental Home
6 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, vacation rental in Chestertown
Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, vacation rental in Chestertown
Dog-friendly, lakefront camp cabin w/ a dock & multiple decks, vacation rental in Chestertown

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New listing! Lakefront cabin with beautiful views, lake and beach access, vacation rental in Chestertown
New listing! Lakefront cabin with beautiful views, lake and beach access, vacation rental in Chestertown
New listing! Lakefront cabin with beautiful views, lake and beach access, vacation rental in Chestertown

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Friends Lake- Quaint and New, vacation rental in Chestertown
Friends Lake- Quaint and New, vacation rental in Chestertown
Friends Lake- Quaint and New, vacation rental in Chestertown

Friends Lake- Quaint and New

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

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

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

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, vacation rental in Chestertown
Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, vacation rental in Chestertown
Lakefront home w/WiFi, dock, lake views from deck & screened-on porch!, vacation rental in Chestertown

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!, vacation rental in Chestertown

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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