Holiday rentals in Highlands

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highlands

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Flat in Cornwall-on-Hudson

4.92 out of 5 average rating, 112 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Guest favourite

Flat in Philipstown

4.91 out of 5 average rating, 233 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Top guest favourite

Flat in Cornwall-on-Hudson

4.98 out of 5 average rating, 221 reviews

Charming Efficiency

Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

Guest favourite

Guest suite in Cold Spring

4.91 out of 5 average rating, 11 reviews

Private Walk-Out Basement Suite

Updated in 2024, this walk-out basement private bedroom suite includes a private entrance, bedroom, bathroom, desk and chair, sleeper chair, and outdoor sitting area. Located 2 minutes from the Cold Spring train station and just a couple blocks from Main Street. Short walk to hiking trails. Use of back yard patio, garden, and fire pit (upon request) included. Mini-fridge and Keurig included. This suite is only rented out when the owners are traveling, so there is no overhead noise.

Guest favourite

Home in Fort Montgomery

4.92 out of 5 average rating, 38 reviews

West Point Cottage

Charming cottage home in the West Point area. 4 miles from the academy in the lower Hudson Valley. Nestled next to the Hudson River and also close to the train into Manhattan. Plenty of walkable historic towns with quaint shops and well regarded restaurants nearby. You will have the first floor, deck, kitchen, bedroom, bathroom, and living room to yourself. We want anyone supporting the academy, the Lower Hudson Valley, and the greatest city in the world, to enjoy it all.

Superhost

Farm stay in Fort Montgomery

4.94 out of 5 average rating, 252 reviews

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

Top guest favourite

Guest suite in New Windsor

4.96 out of 5 average rating, 224 reviews

Large Sunny Studio Peaceful Private Baked Goodies

Large high-ceilinged sunny loft studio. Totally private. Located in Cornwall/New Windsor neighborhood -Ask about our Single Traveler Discount Features -Two super comfy queen sized beds. -Heated Jacuzzi bathtub with bath salts. -Coffee/Tea Bar/Snacks -Home Baked Goodies -Safe. Secure. Private driveway. Parking at door. -Dedicated work desk. -Must be 25 years or older. No parties or gatherings. -2 guest maximum -No 3rd party bookings -Overnight stay - not a hang out.

Superhost

Flat in Cold Spring

4.91 out of 5 average rating, 123 reviews

Historic Penthouse

Private and quiet, cozy one bedroom apartment in the center of the Village, but you’ll feel as if you are a world away, with access to our private Garden and Koi Pond. Just a 7 minute walk to the Metro North train. Within walking distance to everything: Shopping, fine or casual dining, the Hudson River, hiking trails (Breakneck Ridge), even a supermarket, drug store, and post office! Off street parking for one (1) automobile from Friday 9am-Sunday 6pm and holidays.

Top guest favourite

Home in Highland Falls

4.99 out of 5 average rating, 168 reviews

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!

Top guest favourite

Home in Highland Falls

4.98 out of 5 average rating, 101 reviews

Bear Mountain, Westpoint, & Hikers Retreat

The Fort @Fort Montgomery, Westpoint/Bear Mountain New to the rental market! This recently renovated 900 Square foot single story home located 5 miles/7 mins from West Point Military Academy and 3 miles/ 3min from Bear Mountain is the ideal spot for friends and family to convene for a weekend visit in the Hudson Valley.

Top guest favourite

Guest suite in Putnam Valley

4.99 out of 5 average rating, 122 reviews

Nestled in Nature

Welcome to the Hudson Valley, just an hour from Midtown! We’re situated a few minutes from Fahnestock State Park, scenic Cold Spring, and a revitalized Peekskill! While these and many more attractions are nearby, the peace and serenity of our house and property are a welcome change of pace from the city.

Top guest favourite

Flat in Cold Spring

4.97 out of 5 average rating, 70 reviews

Charming Village Apartment - walk to Metro North

Charming 1 BR apartment in the heart of Cold Spring. Centrally located in walking distance to restaurants and shops as well as hiking trails. About 15 min walk from Cold Spring train station. Ideally located in a Town Home in the village of Cold Spring with a private entrance.