
House vacation rentals in Highlands
Find and book unique houses on Airbnb
Top-rated house rentals in Highlands
Guests agree: these houses are highly rated for location, cleanliness, and more.

Entire Home (private pool), Event Friendly
This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Modern 3BD West Point USMA House w/ HotTub!
Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

Your West Point Academy Home Away from Home
Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Bear Mtn Haus near hiking trails
Welcome to our cozy and thoroughly cleaned Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, just 60min from NYC, 15 min to Cold Spring shops and restaurants, 8 min drive from the Garrison train stop. Set on the mountainside, we have lovely partial views of the Hudson river. Short drive to Woodbury Commons Premium Outlet mall and close to Storm King, and Beacon. Our house is suitable for 6 people, but can accommodate 8 at an extra charge.

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Spacious, bright 5 bedroom house near West Point
Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Lovely 3BR Home with parking-Walk to WP Gate!
Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

Charming Home in Peekskill NY
Enjoy this stylish home located less than a 10 minute drive from many walking/biking trails and tons of restaurants and local entertainment. It is also a 2 minute drive from the NY Presbyterian Hudson Valley Hospital perfect for Traveling Nurses and other short-term healthcare professionals. The neighborhood is quiet and situated at the end of a cul-de-sac, so there is no through traffic, suitable for walking your dog.

4 Bd Paradise Gorgeous Design Close to All!
Forget your worries in this spacious and serene space. The Riley house is close to Stewart Airport, West Point, NYMA, The Storm King School and Mount Saint Mary College and all the Hudson Valley has to offer. Central to Wallkill, Patterson, and Warwick as well. Extra fees will apply for guests over 6 and pets.
Popular amenities for Highlands house rentals
House rentals with a pool

midcentury mod * POOL * walk out trail 2 mohonk

TheGoshenGetawayPoolHotTubLegoLandArcade

4Br Mountain Brook House on 130 acres w/ trails

Scenic River View Escape | New Paltz

Design Scandi Retreat, Heated Pool, Dogs Welcome

Mountain Creek retreat PH w/pool & hot tub

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings
Weekly house rentals

Highland Falls Home - 1/2 Mile to West Point

Cottage in the village of Cold Spring

Modern 4 bedroom home near West Point & Bear Mt.

Old Grad House, within Cadet Walking Privileges

Mountainside Home (Beacon/Cold Spring)

Arkadia House Mid-century retreat with pool & view

Home in Cold Spring- Farm Stay!

Peaceful & Spacious Retreat
Private house rentals

Sunset House: near West Point, Hiking & Woodbury

Bungalow near West Point on Hudson River

Delightful Home!

Elegant Hideaway: Cozy Cottage in Katonah, NY

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Victorian Eclectic

*Charming Home & Convenient Location w/ Parking*~

Modern, sun-filled farmhouse retreat
Quick stats about house rentals in Highlands

Total vacation rentals
Explore 120 vacation rentals in Highlands

Nightly prices starting at
Highlands vacation rentals start at G$10,455 GYD per night before taxes and fees

Verified guest reviews
Over 5,210 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
120 of Highlands vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highlands rentals

4.9 Average rating
Highlands stays are highly rated by guests—averaging 4.9 out of 5!
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