Highland Lake Vacation Rentals

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Vacation Rentals in Highland Lake

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Monticello NY

With a stay at this vacation home in Monticello, you'll be on the waterfront, within a 15-minute drive of Bethel Woods Center For The Arts and Mongaup River.

Pool

Kitchen

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Narrowsburg NY

Located in Narrowsburg, this vacation home is on the waterfront, within a 5-minute drive of Upper Delaware River and Upper Delaware Scenic and Recreation River.

In the cloud ~your cozy lake house

Swan Lake NY

$308 nightly

$347 total

Dec 10 - Dec 11

Total with taxes and fees

With a stay at this vacation home in Swan Lake, you'll be on the waterfront, within a 10-minute drive of Bethel Woods Center For The Arts and White Sulphur Springs Synagogue.

Lake front on glacial lake, swimming, boating, fishing. Floating dock

Milford PA

$268 nightly

$291 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Milford, this vacation home is a 5-minute drive from Sunrise Lake and 8 minutes from Gold Key Beach.

Catskills Getaway: 3BR Retreat w/ Media Room, Near Casino, Bethel Woods & More!

Glen Wild NY

$336 nightly

$377 total

Dec 10 - Dec 11

Total with taxes and fees

With a stay at this vacation home in Glen Wild, you'll be in the mountains, within a 10-minute drive of Resorts World Catskills and Neversink River.

Charming 3-bedroom house with AC, WiFi and outdoor hot tub in peaceful Damascus

Damascus PA

Located in Damascus, this vacation home is a 1-minute drive from Upper Delaware River and 6 minutes from Garnet Health Medical Center - Catskills, Grover M. Hermann.

Hot Tub

Kitchen

Breathtaking River Front Cabin

Damascus PA

Located in Damascus, this vacation home is a 1-minute drive from Upper Delaware River and 7 minutes from Garnet Health Medical Center - Catskills, Grover M. Hermann.

NEW 4-bedroom home, private, hot tub, fenced yard, pet friendly

Hawley PA

With a stay at this vacation home in Hawley, you'll be on a lake, within a 15-minute drive of Lake Wallenpaupack and Bingham Park.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Forestburgh NY

$288 nightly

$324 total

Dec 10 - Dec 11

Total with taxes and fees

Located in Forestburgh, this vacation home is on the waterfront, a 3-minute drive from Forestburgh Playhouse and 7 minutes from Mongaup River.

Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,

Matamoras PA

$253 nightly

$275 total

Dec 10 - Dec 11

Total with taxes and fees

With a stay at this vacation home in Matamoras, you'll be a 3-minute walk from Marie's Matamoras Flea Market and 11 minutes by foot from Airport Park.

5 minutes from original Woodstock site.

Mongaup Valley NY

$341 nightly

$383 total

Dec 31 - Jan 1, 2026

Total with taxes and fees

With a stay at this vacation home in Mongaup Valley, you'll be on a river, within a 10-minute drive of Bethel Woods Center For The Arts and Mongaup River.

Lake Front Heated Floors Romantic Hot Tub Firepit Foosball Ski Screen Porch Boat

Eldred NY

Located in Eldred, this vacation home is on the waterfront, within a 15-minute drive of Sidwell Lake and Upper Delaware River.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.