Highland Lake Holiday Homes
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Holiday Homes in Highland Lake

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Our top choices for Highland Lake holiday homes

A covered porch with wicker furniture and a view of a blue house in the background.

A living room with a sofa, dining table, chairs, and a staircase leading to a kitchen.

A serene outdoor area with a large tree, a small building, and a body of water in the background.

A two-story house with a porch and a garage.

1. Sweet Old Farmhouse in a Tranquil Setting

Sweet Old Farmhouse in a Tranquil Setting

Highland Lake

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"

Anne H.

The price is NZ$777

NZ$777

includes taxes & fees

7 Oct - 8 Oct

Sweet Old Farmhouse in a Tranquil Setting

A backyard with a fire pit, outdoor furniture, and a deck.

A modern living room with a green sofa, a fireplace, and a kitchen in the background.

A small, single-story house with a stone chimney, a front porch, and a pathway leading to the entrance.

A modern bedroom with a wooden headboard, a large bed with patterned bedding, two wall-mounted lights, and a bedside table with a plant and candles.

2. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Eldred

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"The place is exactly as described. Very comfortable and had everything we needed to enjoy our stay. Private and quiet. Bed was very comfortable. Pecks market close by. Will stay again."

Robert R.

The price is NZ$826

NZ$826

includes taxes & fees

11 Oct - 12 Oct

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

A living room with a fireplace, sofa, TV, and a wooden table with baskets.

A wooden deck with a bright red door, a potted plant with red flowers, and a red chair.

A modern living room with a grey sectional sofa, patterned rug, and a small wooden side table.

A modern kitchen with white cabinets, a wooden countertop, stainless steel appliances, and pendant lighting.

3. Bright, Spotless Cottage Near Bethel Woods

Bright, Spotless Cottage Near Bethel Woods

Highland

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"This was the perfect place for a long weekend where we wanted to be disconnected yet still have modern amenities. Everything was great from the check in process to the place itself and the location. Looking forward to staying here again in the future!"

Chloe

The price is NZ$514

NZ$514

includes taxes & fees

4 Oct - 5 Oct

Bright, Spotless Cottage Near Bethel Woods

A window with a view of a green, leafy outdoor area, possibly a garden or park.

A small, illuminated wooden structure with a porch and steps leading up to a door.

A kitchen with a gas stove, a kettle, and a window with a view of greenery.

A skylight with a wooden ladder leading to a ceiling fan.

4. Trails Head Tiny House

Trails Head Tiny House

Rock Hill

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"Host was very friendly and helpful. "

Michael R.

The price is NZ$238

NZ$238

includes taxes & fees

1 Nov - 2 Nov

Trails Head Tiny House

A cabin with a wooden deck and a staircase leading to a second-story balcony.

A spacious living area with wooden flooring, a dining table, a sofa, and a bookshelf.

A spacious living area with a high ceiling, wooden beams, a dining table with chairs, a sofa with patterned cushions, and a staircase leading to an upper level.

A rustic wooden staircase leading to a covered wooden deck, surrounded by a stone wall and lush greenery.

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

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

Narrowsburg

10.0 out of 10, Exceptional, (163 reviews)

10/10

Exceptional

(163 reviews)

"Such a beautiful place to stay and explore with my pup!"

Alison H.

The price is NZ$535

NZ$535

includes taxes & fees

15 Oct - 16 Oct

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

A wooden staircase leading to a garden area with a pathway, rocks, and plants.

A grassy outdoor area with a house in the background.

A window view of a forested area with a path and string lights.

A cozy cabin interior with a wooden ceiling, a TV mounted on the wall, a sofa, two patterned armchairs, and a coffee table.

6. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

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

Forestburgh

9.6 out of 10, Exceptional, (16 reviews)

9.6/10

Exceptional

(16 reviews)

"5 stars across the board! Super communicative host, even offered to change cleaning crew schedule to accommodate our needs. There is a beautiful creek going through the back yard. It’s lovely. I feel like pictures dont do it justice. Definitely a wonderful experience."

Dea

The price is NZ$661

NZ$661

includes taxes & fees

6 Oct - 7 Oct

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

A two-story house with a covered porch, a front door, and a staircase leading to the entrance.

A bedroom with a sloped ceiling, skylights, a ceiling fan, a bed with a striped blanket, a bench, and a desk.

A two-story house with a swimming pool, a covered patio with lounge chairs, and a fenced yard.

A wooden deck with outdoor furniture, a grill, and a covered area with a sliding door.

7. Spacious 4 bedroom house with a private pool in a quiet area

Spacious 4 bedroom house with a private pool in a quiet area

Glen Spey

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great place"

Johnny A.

The price is NZ$854

NZ$854

includes taxes & fees

7 Oct - 8 Oct

Spacious 4 bedroom house with a private pool in a quiet area

A large wooden log cabin with a prominent tower and multiple windows.

A kitchen with a gas stove, a sink, wooden cabinets, and a window.

A forested area with a cabin and a wooden structure.

A cozy living room with a sofa, armchairs, and a dining area with wooden furniture.

8. Peaceful retreat above the Delaware River

Peaceful retreat above the Delaware River

Pond Eddy

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Top notch"

Rich D.

The price is NZ$790

NZ$790

includes taxes & fees

5 Oct - 6 Oct

Peaceful retreat above the Delaware River

A modern kitchen with a central island, dark cabinetry, and a hanging pendant light.

A modern kitchen with a dining area, a large window, and a view of the outdoors.

A patio with Adirondack chairs, a fire pit, and a string of lights.

A modern kitchen with dark cabinets, stainless steel appliances, and a central island.

9. Private Hot Tub * Forest Retreat * Near River

Private Hot Tub * Forest Retreat * Near River

Glen Spey

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Rented this house for a family get away weekend. The house was immaculate. The kitchen anything you could possibly need to cook for your group. Nice place. Good value "

Sarah G.

The price is NZ$1,892

NZ$1,892

includes taxes & fees

19 Oct - 20 Oct

Private Hot Tub * Forest Retreat * Near River

A dining area with a wooden table and chairs, a hanging light fixture, and a view of the outdoors through large windows.

A covered porch with a sofa, chairs, and a table.

A calm lake with a wooden dock extending into the water, a boat docked at the pier, and a forested shoreline in the background.

A modern kitchen with a wooden dining table, white chairs, and a brick backsplash.

10. Lakefront Home on Woodstock Way

Lakefront Home on Woodstock Way

White Lake

9.2 out of 10, Wonderful, (12 reviews)

9.2/10

Wonderful

(12 reviews)

"We had a great time staying at the property. The lake front house and lake access was very nice. Owner/Property manager was great to work with. A great overall experience and would recommend this highly!"

Nolan B.

The price is NZ$713

NZ$713

includes taxes & fees

5 Oct - 6 Oct

Lakefront Home on Woodstock Way

11. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home

Montague

9.2 out of 10, Wonderful, (19 reviews)

9.2/10

Wonderful

(19 reviews)

"House was very homey feeling, very dog friendly with large yard."

Catherine F.

The price is NZ$329

NZ$329

includes taxes & fees

5 Oct - 6 Oct

Scenic Views & River Access, Cozy River Home

An outdoor deck with a wooden table and chairs, a grill, and a hot tub.

A kitchen with white subway tile backsplash, wooden shelves, and various kitchen items.

A dining table with various glassware and bowls, white chairs, and a kitchen area with white cabinets and a shelf.

A modern living room with two grey sofas, a wooden coffee table, and two side tables with lamps. There is a ceiling fan and large windows with blinds.

12. Luxury Retreat w/ Hot Tub - near Bethel Woods!

Luxury Retreat w/ Hot Tub - near Bethel Woods!

Forestburgh

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"This was an excellent property.It was clean, well stocked and beautiful. The host was attentive and available. It was really a wonderful stay."

mary

The price is NZ$1,170

NZ$1,170

includes taxes & fees

4 Oct - 5 Oct

Luxury Retreat w/ Hot Tub - near Bethel Woods!

A house with a stone chimney, surrounded by a lush garden and outdoor seating area with Adirondack chairs.

Relax, and have a glass of wine while enjoying forest views

A single-story house with a red door, a chimney, and a porch.

A spacious living area with a sofa, coffee table, and leather chair, a kitchen with modern appliances, and a dining area with bar stools.

13. NEW: Modern And Sunny * Fireplace * Narrowsburg

NEW: Modern And Sunny * Fireplace * Narrowsburg

Narrowsburg

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Amazing hosts! Would rent from them anytime"

Lisa C. K.

The price is NZ$1,079

NZ$1,079

includes taxes & fees

6 Oct - 7 Oct

NEW: Modern And Sunny * Fireplace * Narrowsburg

A covered deck with outdoor seating and string lights.

Living room with fireplace, cozy sitting area, Smart TV with Netflix

A house with a garage, a tree in front, and two parked cars.

Full equipped kitchen with fridge, microwave, oven, stove, toaster, coffee bar

14. Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

Sparrow Bush

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great stay, host was very responsive, would definitely stay again! "

Shriraj S.

The price is NZ$499

NZ$499

includes taxes & fees

6 Oct - 7 Oct

Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

A grassy outdoor area with a stone fire pit, benches, and a house in the background.

A modern kitchen with dark cabinetry, a central island, and a large window providing natural light.

A spacious kitchen with a stone fireplace, a dining area with a long table, and a view of the kitchen through a glass door.

A stone house with a stone roof, surrounded by trees and a wooden cart.

15. Spacious Home on 5 Acres 2 Hrs to NYC

Spacious Home on 5 Acres 2 Hrs to NYC

Pond Eddy

Spacious Home on 5 Acres 2 Hrs to NYC

A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

A living room with a wooden staircase, a black leather sofa, a TV on a stand, and a patterned rug.

A grassy outdoor area with several white lounge chairs and a picnic table.

An above-ground swimming pool with a built-in ladder, surrounded by a gravel border and grass.

16. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.

Mongaup Valley

9.8 out of 10, Exceptional, (76 reviews)

9.8/10

Exceptional

(76 reviews)

"The house was really nice. Decorated in line with the area. Plus, Bruce was a great host."

Robert

The price is NZ$658

NZ$658

includes taxes & fees

6 Oct - 7 Oct

5 minutes from original Woodstock site.

Dining room area- has extendable table to accommodate 10 people

17. Rare River Views & Access, Cabin by Eden Islands

Rare River Views & Access, Cabin by Eden Islands

Montague

9.0 out of 10, Wonderful, (16 reviews)

9.0/10

Wonderful

(16 reviews)

"Host was accessible and very nice location to enjoy what nature brings."

Rohan L.

The price is NZ$310

NZ$310

includes taxes & fees

7 Oct - 8 Oct

Rare River Views & Access, Cabin by Eden Islands

A deck with two chairs and a table, overlooking a grassy area with trees and a body of water.

A stone fireplace with a glass door, a wooden bench, and a view of the outdoors.

A home gym with exercise equipment, large windows, and a view of a snowy landscape.

A bedroom with a bed, a television mounted on the wall, and a window.

18. Lake House Heated Pool Hot Tub Kayaks FirePit Screened Patio Foosball Fireplace

Lake House Heated Pool Hot Tub Kayaks FirePit Screened Patio Foosball Fireplace

Eldred

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Such a beautiful spot on the lake! Our family enjoyed the pool, hot tub, and kayaks. House was clean and comfortable. We would love to go back!"

Carrie K.

The price is NZ$1,651

NZ$1,651

includes taxes & fees

7 Oct - 8 Oct

Lake House Heated Pool Hot Tub Kayaks FirePit Screened Patio Foosball Fireplace

A living room with a wooden floor, a white console table with plants, a grey sofa with patterned cushions, a round white coffee table, a flat-screen TV, and a ceiling fan.

19. Forest and River Side Tranquil House

Forest and River Side Tranquil House

Montague

7.8 out of 10, Good, (19 reviews)

7.8/10

Good

(19 reviews)

"Over all ok property. A bit outdated but comfortable. Check on and out very smooth and easy."

Connie B.

The price is NZ$329

NZ$329

includes taxes & fees

7 Oct - 8 Oct

Forest and River Side Tranquil House

A cozy room with a stone wall, a large window, a blue cabinet, and a striped armchair.

A modern interior with a dining area, a large sliding glass door leading to a balcony, and a view of the outdoors.

A cozy living room with a fireplace, two armchairs, a sofa, and a coffee table.

A covered porch with stone walls, a door, and two wicker chairs with cushions.

20. River Views * Fireplace * Sunroom * Walk to Town

River Views * Fireplace * Sunroom * Walk to Town

Narrowsburg

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"This property was beautiful, comfortable, and clean. It has everything you need, but not so much it is overwhelming or cluttered. If I go back up again, I would definitely book this again."

Audrey H.

The price is NZ$1,028

NZ$1,028

includes taxes & fees

26 Oct - 27 Oct

River Views * Fireplace * Sunroom * Walk to Town

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.

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Top Highland Lake Hotel Reviews

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent

"Always pleasant to stay here."

Lonzie 1-night trip

Posted 21 hours ago

Best Western Hunt's Landing Hotel Matamoras/Milford

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent

"Convenient drive to Bethel Woods for a concert. Nice, clean hotel."

Mark 1-night trip

Posted 22 hours ago

Days Inn by Wyndham Liberty/Monticello

Kenoza Lake View Manor

10/10 Excellent

"Super friendly owner, great conversation, felt like a friend instead of a guest . Stayed for a concert at Bethel Woods, they had a shuttle available. I didn't use it, but nice to know it was available Comfortable inn with cozy rooms"

Gale 2-night trip

Posted 2 days ago

Kenoza Lake View Manor

Days Inn by Wyndham Wurtsboro

10/10 Excellent

"I love the jaquzy it was beautiful. Tha staff very friendly and helpful I recommend this place any time !!!"

Mariely 2-night trip

Posted 2 days ago

Days Inn by Wyndham Wurtsboro

The Hotel Belvidere

10/10 Excellent

"Very clean, comfortable room"

Allen 1-night trip

Posted 5 days ago

The Hotel Belvidere

Hampton Inn Monticello

10/10 Excellent

"It was great"

Tamta 1-night trip

Posted 6 days ago

Hampton Inn Monticello

2 Lake Cabins | Pool+HotTub | Game Room & Courts

10/10 Excellent

"Beautiful spot! Every amenity is provided! Comfortable and clean."

James D. 3-night trip

Posted 3 months ago

2 Lake Cabins | Pool+HotTub | Game Room & Courts

Find out more about Highland Lake

Highland Lake Holiday Homes information

Number of reviews	217
Accommodation	345 Holiday Homes
Lowest Price	NZ$238
Highest Price	NZ$1,892

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Highland Lake on Expedia.com

Holiday Homes in Highland Lake

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Highland Lake holiday homes

1. Sweet Old Farmhouse in a Tranquil Setting

2. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

3. Bright, Spotless Cottage Near Bethel Woods

4. Trails Head Tiny House

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

6. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

7. Spacious 4 bedroom house with a private pool in a quiet area

8. Peaceful retreat above the Delaware River

9. Private Hot Tub * Forest Retreat * Near River

10. Lakefront Home on Woodstock Way

11. Scenic Views & River Access, Cozy River Home

12. Luxury Retreat w/ Hot Tub - near Bethel Woods!

13. NEW: Modern And Sunny * Fireplace * Narrowsburg

14. Cozy River Valley Family Retreat w/ Fireplace, Games & Serene Deck

15. Spacious Home on 5 Acres 2 Hrs to NYC

16. 5 minutes from original Woodstock site.

17. Rare River Views & Access, Cabin by Eden Islands

18. Lake House Heated Pool Hot Tub Kayaks FirePit Screened Patio Foosball Fireplace

19. Forest and River Side Tranquil House

20. River Views * Fireplace * Sunroom * Walk to Town

Find holiday rentals that suit your style

Top Highland Lake Hotel Reviews

Best Western Hunt's Landing Hotel Matamoras/Milford

Find out more about Highland Lake

Highland Lake Holiday Homes information

Explore a world of travel with Expedia