Highland Lake Holiday Rentals, New York: Private House Rentals

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Go beyond your typical stay in Highland Lake

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Our top choices for Highland Lake hotels

An indoor water park with a large water slide, inflatable tubes, and lush greenery.

A modern kitchen with granite countertops, a dining area with a large table and chairs, and a ceiling fan.

A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

A multi-tiered pagoda-style building with a central tower, surrounded by a covered walkway and open areas.

1. 2 Lake Cabins Pool+hottub Game Room 23acs

Highland Lake

Rp6.218.208

Rp24.103.649 total

includes taxes & fees

22 Oct - 23 Oct

A lakeside walkway with a wooden deck, surrounded by trees and a building with illuminated windows.

A restaurant with a long dining table, multiple chairs, and a high ceiling with hanging lights.

A modern interior with a piano, bar area, and seating.

A modern living room with a stone fireplace, wicker furniture, and a flat-screen TV mounted on the wall.

2. The Bradstan Boutique Hotel

Eldred

Deborah

Rp5.973.791

Rp7.018.867 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.

An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.

A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.

A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

3. Hampton Inn Monticello

Monticello

ANN

Rp2.206.052

Rp2.492.838 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.

A modern restaurant interior with round tables and booths, pendant lighting, and a view of the street through large windows.

4. Resorts World Catskills Casino

Monticello

michael

Rp2.861.845

Rp3.681.361 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with two sofas, a glass coffee table, and a painting of a horse.

A large indoor swimming pool with a wooden deck and lounge chairs.

A modern breakfast bar with a variety of food options, including a juice bar and coffee machines.

A reception area with a marble counter, a wall-mounted artwork, and a ceiling with recessed lighting.

5. Best Western Monticello

Monticello

Sonia

Rp2.031.894

Rp2.296.041 total

includes taxes & fees

18 Oct - 19 Oct

A spacious lobby with a stone fireplace, a flat-screen TV, and comfortable seating.

A lobby with a stone fireplace, two armchairs, a coffee table, and a dining area with tables and chairs.

A hotel lobby with a reception desk, a patterned carpet, a stone wall, and a seating area with a checkered sofa and ottoman.

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled wall.

6. Hampton Inn Matamoras/Milford

Matamoras

brian

Rp1.719.199

Rp1.873.927 total

includes taxes & fees

8 Nov - 9 Nov

A snow-covered outdoor area with picnic tables and brick structures, likely a campground or park.

A room with a wooden table, a potted plant, a television, and a small cabinet.

A bedroom with a bed, bedside table, lamp, and a view of the outdoors.

A bedroom with a wooden bed, a brown leather chair, a round woven ottoman, a white bedside table with a lamp, and a mirror on the wall.

7. The Drift House

Barryville

David

Rp2.400.256

Rp2.712.235 total

includes taxes & fees

14 Oct - 15 Oct

An indoor water park with a large water slide, a pool area, and a glass ceiling structure.

A modern building with a sign reading "The Kartrite Resort & Indoor Waterpark".

A restaurant setting with a counter, a digital scale, and a person serving food.

A hotel with a pool area, outdoor seating, and a view of the sunset.

8. The Kartrite Resort & Indoor Waterpark

Monticello

Danely

A row of white cabins with red shutters, each featuring a porch and a small front yard.

A wooden reception desk with a sign reading "EST 1945" and various items like a framed picture, a calendar, and a display stand with cards.

A room with two blue patterned armchairs, a wooden coffee table with a flower vase, a lamp, and a window with white curtains.

A counter with brochures and a vending machine.

9. Myer Motel

Milford

theodore

Rp1.700.405

Rp1.853.441 total

includes taxes & fees

12 Oct - 13 Oct

An indoor swimming pool with a central column, tiled floor, and a skylight above.

An outdoor bar area with a stainless steel counter, bar stools, and a variety of bottles.

A spacious dining area with long tables and chairs, high ceilings with exposed beams, and hanging pendant lights.

10. The Alder at Resorts World Catskills

Monticello

John

Rp2.464.871

Rp3.232.917 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a staircase, a dining area, and a decorative metal piece on the wall.

A dining room with a wooden table, six chairs, a chandelier, a grandfather clock, and a bookshelf.

A modern kitchen with dark cabinetry, a stainless steel microwave, and an oven.

A single-story house with a front porch, a visible front door, and a small front yard with a concrete path leading to the door.

11. Windsong Retreat 2

Bethel

Joseph

Rp4.993.821

Rp6.350.924 total

includes taxes & fees

12 Oct - 13 Oct

A modern lobby with a wooden accent wall, a seating area with sofas and ottomans, and a 'Museum Store' sign.

A covered patio area with stone pillars, wooden benches, and a view of a lake.

A spacious indoor area with large windows and a high ceiling, suitable for group activities like yoga.

A person in a swimming pool with a tiled wall in the background.

12. YO1 Longevity & Health Resorts, Catskills

Monticello

Rajvi

Rp6.242.276

Rp7.053.771 total

includes taxes & fees

12 Oct - 13 Oct

A small, standalone structure with a pitched roof, possibly a gazebo or shelter, surrounded by well-maintained grass and plants. In the background, there is a sign for 'Scottish Inns' indicating the presence of a hotel nearby.

A row of motel-style buildings with a central statue in a landscaped area.

A living room with a stone fireplace, a brown leather sofa, a framed picture on the wall, and a small plant.

13. Scottish Inns Milford

Milford

Kellie

Rp1.610.910

Rp1.755.892 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a living area, a sofa, a coffee table, a TV, and a large window with a view.

A breakfast area with six round tables and chairs, a coffee station, and a view of greenery outside.

A hallway with a black door, a potted plant, and a refrigerator in the background.

14. Days Inn by Wyndham Wurtsboro

Wurtsboro

Danny

Rp1.950.991

Rp2.204.621 total

includes taxes & fees

12 Oct - 13 Oct

A bar area with a long counter, multiple stools, and a variety of bottles and glasses.

A hallway with a wooden floor, glass doors, and a sign for Annie's Lounge.

A spacious dining area with multiple tables and chairs, a high ceiling with grid patterns, and large abstract paintings on the walls.

A spacious living area with a stone wall, wooden ceiling beams, and large windows offering a view of the outdoors.

15. Best Western Hunt's Landing Hotel Matamoras/Milford

Matamoras

Lonzie

Rp2.160.588

Rp2.355.041 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a desk, a lamp, and a painting on the wall.

A reception area with patterned wallpaper, a wooden counter, a display of magazines, and a door with a view of the outside.

A motel entrance with a blue awning, a metal staircase, and hanging flower baskets.

16. Rodeway Inn Milford - I-84

Milford

Jacqueline

Rp1.597.486

Rp1.741.260 total

includes taxes & fees

8 Nov - 9 Nov

A bar area with a curved counter, multiple hanging pendant lights, and a variety of bottles and glasses on shelves.

A room with a wooden floor, a white armchair, a wooden cabinet, a television mounted on the wall, and a window with curtains.

A cozy hotel room with a wooden floor, a striped sofa, a wooden coffee table, a chair, a lamp, and a painting on the wall.

A neatly arranged bedroom with a large bed, two bedside tables with lamps, a chair, and a window with curtains.

17. Tom Quick Inn

Milford

GERALDINE

Rp1.896.041

Rp2.102.483 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with tables set for a meal, large windows offering a view of greenery, and a grand piano in the background.

A porch with striped awnings, a black door, and a bench.

A spacious lounge with a sofa, chairs, and a coffee table, surrounded by large windows and various plants.

A brick-paved walkway leading to a white building with a white fence and a tree with autumn leaves.

18. Hotel Fauchere

Milford

John

Rp4.577.490

Rp5.025.144 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with two beds, a desk, a chair, a lamp, and artwork on the walls.

A hotel room with a desk, chair, television, and a minibar.

A two-story house with a gabled roof, a chimney, and an American flag.

A bathroom with a white sink, two faucets, a mirror, and a toilet.

19. Super 8 by Wyndham Monticello NY

Monticello

Marlene

Rp1.433.531

Rp1.619.889 total

includes taxes & fees

13 Oct - 14 Oct

A garden with a rock fountain surrounded by various plants and flowers.

A white building with green trim and windows, a flag, and a picket fence with red bows.

A dining table set with ornate plates, silverware, and glassware, surrounded by vintage-style chairs.

A snowy landscape with a river, trees, and a metal railing.

20. John H Wallace House

Milford

Donna

Rp4.110.147

Rp4.480.120 total

includes taxes & fees

8 Nov - 9 Nov

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Top Highland Lake Hotel Reviews

Hampton Inn Matamoras/Milford

10/10 Excellent

"Place was overall a good place. I would definitely stay again good good food choices for breakfast."

The Alder at Resorts World Catskills

8/10 Good

"Considering this was a resort hotel, I would’ve expected spa Jacuzzi or a hot tub or a pool and at least continental breakfast and they didn’t seem to have any of that plus the staff wasn’t overly friendly either"

Best Western Monticello

8/10 Good

"Everything was good."

Best Western Hunt's Landing Hotel Matamoras/Milford

8/10 Good

"The rooms need some updating ."

High Point Motel

10/10 Excellent

"Melanie is super sweet, and extremely helpful. She always goes above and beyond to make sure everything is perfect. Even the decorations are perfect. Its by far the coziest place to stay, definitely worth the trip. And the staff is amazing 👏 We always appreciate everything ❤️"

The Bradstan Boutique Hotel

10/10 Excellent

"Everything at the property was just perfect from welcoming staff at check in to a delicious complimentary breakfast. We had the signature suite and could not have been happier with everything about it. The property grounds were so beautiful."

Silver Birches

10/10 Excellent

"Our room was clean and comfortable. It was nice to have breakfast provided every day. And of course, the lake view is spectacular!"

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent

"Restaurant was amazing . Staff very informative about history of Woodstock"

More cheap stays in Highland Lake