Holiday rentals in Highland Lake

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Top-rated holiday rentals in Highland Lake

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Guest favourite

Home in Glen Spey

4.98 out of 5 average rating, 114 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakeside retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,fine dining etc all within 20 min!!

3–10 May

€ 417 per night

Guest favourite

Cottage in Narrowsburg

4.99 out of 5 average rating, 143 reviews

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

5–12 May

€ 129 per night

Guest favourite

Home in Glen Spey

5.0 out of 5 average rating, 15 reviews

Cozy and Quiet Lakeview House

Looking for a cozy and quiet getaway near a lake? Look no further than this newly renovated house that offers one bedroom and sleeper sofas for extra guests. Enjoy the views of the lake from the large windows, or cozy up by the firepit in the backyard. This house has everything you need for a relaxing and comfortable stay, including a equipped kitchen, a bathroom, and a smart TV. Whether you want to explore the nearby trails, go fishing, or just unwind, this house is the perfect place for you.

13–20 Dec

€ 143 per night

Guest favourite

Flat in Pond Eddy

4.96 out of 5 average rating, 304 reviews

Delaware Riverfront

This isn’t a cold, clinical, ultra-modern, cooperate-owned product masquerading as a home. Come here for a taste of humanity, surprise, old-fashioned American décor, and an intriguing setting of items not seen over and over again in clone rental units around the area. Rather than trying to transplant an urban style/faux glamour to the Upstate experience, we endeavor to give the comforts and intriguing whatnots, knickknacks, curiosities and lost charms perhaps seen in your grandparents’ home.

20–27 Mar

€ 169 per night

Guest favourite

Cabin in Highland

5.0 out of 5 average rating, 12 reviews

LakeFront Getaway/Near Water Rafting/Gameroom/Pets

Spacious Yet Cozy Lake Cabin - Newly renovated with upgraded features: - Heated floors - Brand New High-end Appliances - Alexa Echo controlled TV's/Speakers - Alkaline Filtered Drinking Water (No need to bring water bottles) - 4 Vehicle Car Port with motion lights - EV Charger - Generator Located 2 hours from NYC and 20 mins from Port Jervis Metro North Train & eateries: - 5 Mins to Local Supermarket/Pizza - 10 Mins to Water Rafting - 20 Mins to Big Bear Mtn Ski Lodge - 30 Mins to Walmart

16–23 Sep

€ 402 per night

Guest favourite

Cabin in Mongaup Valley

4.92 out of 5 average rating, 284 reviews

Cozy Post & Beam Barn Cabin w/Park near Bethel

1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

26 Sep – 3 Oct

€ 149 per night

Guest favourite

Home in Narrowsburg

4.95 out of 5 average rating, 159 reviews

Modern Getaway in the Catskills

Our summer rental has a private entrance adjacent to the main house with kitchen, living & dining rooms, 1 bedroom w/ Queen bed , AC and 1.5 baths. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and WiFi. A great get-a-way for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets or animals or children. All are welcome. Rainbow Friendly.

15–22 Sep

€ 83 per night

Guest favourite

Home in Highland Lake

5.0 out of 5 average rating, 38 reviews

Lakefront Serenity: Prvt Pickleball, Games, Sauna

Under 2 hours from NYC you'll be swimming, fishing, and kayaking in no time. Our game room is fully equipped with pool, ping pong, Foose ball, and darts, providing endless entertainment options for kids and adults. You can also play a game of pickleball/basketball outside on the court, roast marshmallows around the fire pit, kayak around the lake, or simply relax in the indoor sauna. Our fully stocked kitchen has everything you need to prepare meals for your family and friends.

7–14 Dec

€ 1,036 per night

Guest favourite

Cottage in Eldred

4.98 out of 5 average rating, 104 reviews

Bella Cottage w/Cozy Fireplace, Winter Getaway

Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

18–23 Apr

€ 349 per night

Guest favourite

Home in Eldred

5.0 out of 5 average rating, 21 reviews

Pristine Country Cottage With Lake Access

Enjoy the perfect balance between country and convenience. Take a short stroll down to Lake Montgomery where you can fish, swim, or take our 3-person canoe out for a relaxing day on the water. Our country cottage is located just a mile and a half from the hamlet of Eldred where you'll find a local brewery, an open air pizzeria, a a hydroponic farm, grocery shopping, and more.

13–20 Feb

€ 187 per night

Guest favourite

Holiday home in Highland Lake

5.0 out of 5 average rating, 25 reviews

Family Gateway in Highland Lake, NY.

Nestled on 5 wooded acres this modern family home is located on a picturesque and peaceful property. In the winter enjoy lovely snow covered trees and landscapes. Build a snowman in the yard or go skiing at local ski hills. Some trails are open for hiking. Inquire about local winter fest or family tubing/ ice skating possibilities. Come enjoy a true family retreat!

21–28 Sep

€ 349 per night

Guest favourite

Guest house in Mongaup Valley

4.96 out of 5 average rating, 242 reviews

Cozy Cottage - Woodstock Scavenger Hunt w/ prize

The cottage is a cozy little space with great amenities. Jam out with the SONOS speaker or watch any channel on DirecTV during the down time. Large back porch and beautiful gardens with a little pond surrounding the home. We also have a Woodstock themed scavenger hunt for any guest who would like to participate! Prize included for anyone who solves all the clues!!

13–20 Sep

€ 120 per night