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Highland Lake Holiday Rentals

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50 rentals in Highland Lake.
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Cozy Lakeside Cottage with Spacious Deck & Grill!, holiday rental in Highland Lake

Cozy Lakeside Cottage with Spacious Deck & Grill!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fall Fun!  Lake Home on private Highland Lake across the road., holiday rental in Highland Lake

Fall Fun! Lake Home on private Highland Lake across the road.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Catskills/Delaware River /Private Mountain Home/100 from NYC/ Ski/Raft/Fish, holiday rental in Highland Lake

New Catskills/Delaware River /Private Mountain Home/100 from NYC/ Ski/Raft/Fish

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 4BR Chalet-5 Mins. to Pool/Lake/Ski-Game Room in Basement, holiday rental in Highland Lake

Luxury 4BR Chalet-5 Mins. to Pool/Lake/Ski-Game Room in Basement

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Warm Comfortable Getaway for Family & Friends., holiday rental in Highland Lake

Warm Comfortable Getaway for Family & Friends.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Luxe Country Home in the Swinging Bridge Lake Community, holiday rental in Highland Lake

Luxe Country Home in the Swinging Bridge Lake Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 2 Master suite with Hot Tub & Sauna, holiday rental in Highland Lake

Luxury 2 Master suite with Hot Tub & Sauna

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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ITS BACK UP! 5 Bedrooms 4.5 Bathrooms W/ AMAZING Game Room Beautiful Bearadise, holiday rental in Highland Lake

ITS BACK UP! 5 Bedrooms 4.5 Bathrooms W/ AMAZING Game Room Beautiful Bearadise

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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BEAUTIFUL OPEN FLOOR PLAN CHALET WITH TONS OF AMENITIES AND WRAP AROUND DECK, holiday rental in Highland Lake

BEAUTIFUL OPEN FLOOR PLAN CHALET WITH TONS OF AMENITIES AND WRAP AROUND DECK

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Enjoy the tranquility of our beautiful lake., holiday rental in Highland Lake

Enjoy the tranquility of our beautiful lake.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Masthope 4Br+Loft, 2 Baths and Game room. Sleeps 10, holiday rental in Highland Lake

Masthope 4Br+Loft, 2 Baths and Game room. Sleeps 10

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious and Stunning Masthope Chalet with room for 12+  Walk to Lake, holiday rental in Highland Lake

Spacious and Stunning Masthope Chalet with room for 12+ Walk to Lake

4 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Masthope Pocono Retreat, Gorgeous Mountain Views, Fully Renovated, Cul-de-sac, holiday rental in Highland Lake

Masthope Pocono Retreat, Gorgeous Mountain Views, Fully Renovated, Cul-de-sac

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Modern Luxury Catskills Lakefront Home, holiday rental in Highland Lake

Modern Luxury Catskills Lakefront Home

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Getaway with Room for All, holiday rental in Highland Lake

Cozy Getaway with Room for All

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home on White Lake in Bethel, NY, holiday rental in Highland Lake

Waterfront Home on White Lake in Bethel, NY

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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“The Oasis’”  Beautiful private lake front home with In-ground pool and sauna., holiday rental in Highland Lake

“The Oasis’” Beautiful private lake front home with In-ground pool and sauna.

4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Luxury 4BR Chalet - Walking Distance to Lake and 8 min to Skiing/Lodg, holiday rental in Highland Lake

Luxury 4BR Chalet - Walking Distance to Lake and 8 min to Skiing/Lodg

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful woodland cabin with all new furniture, linens, electronics, appliances, holiday rental in Highland Lake

Beautiful woodland cabin with all new furniture, linens, electronics, appliances

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Catskills Home Sleeps 12 in Swinging Bridge Lake Community, holiday rental in Highland Lake

Spacious Catskills Home Sleeps 12 in Swinging Bridge Lake Community

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Water front boating, fishing, swimming, horseride, hike, mini-golf, ski & more!, holiday rental in Highland Lake

Water front boating, fishing, swimming, horseride, hike, mini-golf, ski & more!

5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Mid Century Modern Ranch in Catskills Near River, holiday rental in Highland Lake

Mid Century Modern Ranch in Catskills Near River

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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River Front, Million Dollar Mountain View Estate, holiday rental in Highland Lake

River Front, Million Dollar Mountain View Estate

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Modern Catskills Cottage, holiday rental in Highland Lake

Rustic Modern Catskills Cottage

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Enjoy the Magic of the Catskills in your Private Lakefront Home, holiday rental in Highland Lake

Enjoy the Magic of the Catskills in your Private Lakefront Home

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Delaware Riverfront Log Cabin, holiday rental in Highland Lake

Delaware Riverfront Log Cabin

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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This beautiful location will warm your hearts and make your stay all the more pl, holiday rental in Highland Lake

This beautiful location will warm your hearts and make your stay all the more pl

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Masthope Vacation Retreat, Endless Mountain Views, holiday rental in Highland Lake

Masthope Vacation Retreat, Endless Mountain Views

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Woodstock Way Vacation and Concert Rentals, holiday rental in Highland Lake

Woodstock Way Vacation and Concert Rentals

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Floating Farmhouse: Stunning renovation in storybook setting, 2 hours from NYC, holiday rental in Highland Lake

Floating Farmhouse: Stunning renovation in storybook setting, 2 hours from NYC

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Luxe Lakefront Family Cottage w/ Private Dock, holiday rental in Highland Lake

NEW! Luxe Lakefront Family Cottage w/ Private Dock

9 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Tentrr Signature Site - River's Edge on the Canal, holiday rental in Highland Lake

Tentrr Signature Site - River's Edge on the Canal

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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ESCAPE-REFRESH- Large Riverfront Estate-Pristine, Private, Fresh Air 90Miles GWB, holiday rental in Highland Lake

ESCAPE-REFRESH- Large Riverfront Estate-Pristine, Private, Fresh Air 90Miles GWB

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Catskills Luxury Lake House - New York, United States, holiday rental in Highland Lake

Catskills Luxury Lake House - New York, United States

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary Lake Front - 5 Acres!, holiday rental in Highland Lake

Contemporary Lake Front - 5 Acres!

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly Built & Secluded Catskill Cottage w/ Views!, holiday rental in Highland Lake

Newly Built & Secluded Catskill Cottage w/ Views!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Masthope Home w/Pool & Lake Access - Ski Big Bear!, holiday rental in Highland Lake

Masthope Home w/Pool & Lake Access - Ski Big Bear!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Masthope Mountain Resort Home w/Deck, Pool Access!, holiday rental in Highland Lake

Masthope Mountain Resort Home w/Deck, Pool Access!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bella Red Farm--an enchanting secluded escape on top of a hill in the forrest, holiday rental in Highland Lake

Bella Red Farm--an enchanting secluded escape on top of a hill in the forrest

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Barkley's Resort, holiday rental in Highland Lake

Tentrr Signature Site - Barkley's Resort

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Hidden Creek, holiday rental in Highland Lake

Tentrr Signature Site - Hidden Creek

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - River's Edge Sunset, holiday rental in Highland Lake

Tentrr Signature Site - River's Edge Sunset

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Swinging Bridge Sanctuary, holiday rental in Highland Lake

Tentrr Signature Site - Swinging Bridge Sanctuary

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Waterfall Paradise, Walking Distance to River, holiday rental in Highland Lake

Tentrr Signature Site - Waterfall Paradise, Walking Distance to River

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tiny House on Spectacular Riverfront Property - Private Access to Delaware River, holiday rental in Highland Lake

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Quiet 4 Bedroom House with Lake Views on large field - perfect for family breaks, holiday rental in Highland Lake

Quiet 4 Bedroom House with Lake Views on large field - perfect for family breaks

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Sparrow's Hideaway, holiday rental in Highland Lake

Tentrr Signature Site - Sparrow's Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - River's Edge Sunrise, holiday rental in Highland Lake

Tentrr Signature Site - River's Edge Sunrise

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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NEW! Pet-Friendly Poconos Getaway w/ Resort Perks!, holiday rental in Highland Lake

NEW! Pet-Friendly Poconos Getaway w/ Resort Perks!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Updated Family Home: 1 Mile to Delaware River, holiday rental in Highland Lake

NEW! Updated Family Home: 1 Mile to Delaware River

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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