
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.

NEW! Stylish Home in the Heart of Beacon
This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

Beacon Creek House
Welcome to our serene oasis in Beacon, NY. If Gilmore Girls and Schitt’s Creek had a baby, it would be Beacon. Nestled beside a tranquil creek, our home features 2 cozy bedrooms, a stylish bathroom, and an open living space with a daybed. Designed with wabi-sabi aesthetics and eco-friendly materials. Just steps from Main Street and less than a 5 min drive from the train station, with scenic trails, shops and restaurants nearby. Book your stay and experience our artfully designed home and city!

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

Cozy 3 bedroom house on quiet private road
3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahenstock St Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay. I live close by so I’m available for help or assistance during your stay.

*Large Pool* Garrison Ultra Modern 5B hottub sauna
Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC
"Mitzi" is a clean 2-story house on a quiet residential street/safe area. Eat-in kitchen, dining room, 2 twins, one queen, fold out bed in Living Room, shower/tub, washer/dryer, dedicated work area, Internet TV&ROKU, 2 flrs, large backyard, sml bbq, fire pit, many art supplies, games, books. Free on/off-street parking. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping. Town pool easy walking distance. No river or mountain view directly from house.

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.
Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

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.

Cozy, Modern Retreat in the Woods of Cold Spring
Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

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!

Eagle Rock House
FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Eagle Rock 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.
Popular amenities for Highlands house rentals
House rentals with a pool

Private Hudson Valley Country Retreat

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Modern House with Hot-Tub and Fireplace

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Weekly house rentals

Sunset House: near West Point, Hiking & Woodbury

Fall Splendor at Dr. Ruth’s Lake Retreat

NYC Getaway - Woodbury Commons, Storm King, Skiing

A nice place to getaway

Home in Cold Spring- Farm Stay!

Waterfront Lake House

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Hudson Valley Hideaway: 10 Minutes to Storm King!
Private house rentals

Bungalow near West Point on Hudson River

West Point Family Retreat 5 min walk to Thayer

The Barger Wixon House

Farmhouse w/ Sauna & Hot Tub near Storm King

Victorian Eclectic

Cozy cottage with hot tub and game room

Our Rockbound Retreat

Charming contemporary cottage with lap pool
Quick stats about house rentals in Highlands
Total rentals
110 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
4.8K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- Rentals with pools Highlands
- Hotel rentals Highlands
- Rentals with breakfast Highlands
- Fitness-friendly rentals Highlands
- Rentals with a fire pit Highlands
- Rentals with a washer and dryer Highlands
- Apartment rentals Highlands
- Pet-friendly rentals Highlands
- Rentals with a fireplace Highlands
- Family-friendly rentals Highlands
- Rentals with outdoor seating Highlands
- Rentals with a patio Highlands
- Waterfront rentals Highlands
- House rentals Orange County
- House rentals New York
- House rentals United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Central Park Zoo
- Yankee Stadium
- Mountain Creek Resort
- Citi Field
- Fairfield Beach
- United Nations Headquarters
- Rye Beach
- Grand Central Terminal
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- The Metropolitan Museum of Art
- Astoria Park
- Bronx Zoo
- Minnewaska State Park Preserve
- Walnut Public Beach