Holiday rentals in Highlands

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Top-rated holiday rentals in Highlands

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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.

Superhost

Flat in Newburgh

4.81 out of 5 average rating, 153 reviews

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

Guest favourite

Guest suite in Chester

4.96 out of 5 average rating, 322 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Guest favourite

Flat in Cold Spring

4.95 out of 5 average rating, 110 reviews

Spectacular Cold Spring Views---Walk To Train

Incredible location! This beautifully decorated 3rd Floor, 2-bedroom space with spectacular mountain views is right in the middle of Cold Spring Village. Just off Main Street, it's an easy 3 minute walk to/from the Metro North Station (which is just over an hour by train to/from New York's Grand Central Station). This quiet, convenient sanctuary is only a few steps from charming galleries, shops, restaurants, hiking, boating, kayaking and all amenities that Cold Spring has to offer.

Guest favourite

Guest suite in Cold Spring

4.9 out of 5 average rating, 10 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

Barn in Mountainville

4.97 out of 5 average rating, 122 reviews

Renovated Red 1890’s Hudson Valley Barn

Renovated barn in Mountainville, NY at the base of the Schunnemunk hiking trails. 1 mile from Storm King Art Center. 3 miles to Cornwall. 10 minutes from Woodbury Common Premium Outlet. 15 minutes to West Point. Private stairs & balcony leads to 500 square foot second-story space. You get the entire upstairs to yourself. The NYS Thruway does run between the house and the mountain. There is highway noise. TV has a ROKU. The WiFi signal is weak due to the metal siding on the barn.

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

Guest suite in Cornwall

4.96 out of 5 average rating, 115 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

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

Loft in Mountainville

4.98 out of 5 average rating, 127 reviews

Lovely, Quiet and Very Private! Entire Loft!

Nestled in the mountains is a peaceful place to lay your head. Just a stones throw from vineyards, brewery's and some of the best views and attractions the Hudson Valley has to offer. Here you'll find a private & secluded bedroom and bathroom fit for 2. A small "kitchenette" is avaliable for use as well as an outdoor seating area with fireplace. Free parking in designated spot. Waterfall is a short hike away.

Guest favourite

Guest suite in Marlboro Township

4.96 out of 5 average rating, 185 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Top guest favourite

Cottage in Philipstown

4.99 out of 5 average rating, 203 reviews

Modern Country Cottage by Bear Mountain

Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.