Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favorite

Apartment in Stone Ridge

4.92 out of 5 average rating, 532 reviews

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Guest favorite

Home in New Paltz

4.96 out of 5 average rating, 219 reviews

Eclectic one-bedroom house

This bohemian New Paltz house is 1/3 mi to Main St New Paltz, 2/3 mi to SUNY and 1 1/2 blocks from the New Paltz-Kingston rail trail. Rent entire house with a private bathroom, large deck space with table and grill, small living and dining room, EV charging and a kitchen. The entire upstairs is a spacious and unique bedroom space. Walking distance to many restaurants and bars. New Paltz is a central location for outdoor fun, close to Mohonk, the Gunks, great biking, hiking, rock climbing, etc.

Guest favorite

An inviting front porch features two rocking chairs with blue cushions positioned next to a small wooden table. A potted plant adds a touch of greenery, while a soft rug lies on the wooden floor. A lantern is placed near the entrance, enhancing the welcoming ambiance.

Apartment in New Paltz

4.96 out of 5 average rating, 390 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Guest favorite

A charming street scene captures historic buildings lining both sides of the road, with varied storefronts and signage visible. The morning light casts a warm glow on the brick facades, while parked cars and utility poles create a sense of daily life in the town.

Loft in New Paltz

4.94 out of 5 average rating, 330 reviews

Peaceful Couples Retreat Near Trails, Town & SUNY

Come unwind in our peaceful studio retreat near SUNY, scenic trails, and the Empire State Bike Trail — a perfect spot for a restful getaway. Whether you're escaping the city or visiting friends, this cozy basement-level studio is ideal for couples or solo travelers to relax after a day exploring New Paltz. - 5 Min Walk to Millbrook Preserve - On the Empire State Bike Trail - 20 Min Walk to Main St. - Close to Mohonk, River to Ridge & Minnewaska - Pet Friendly! Sleeps up to 4 (sofa bed)

Guest favorite

A clean bathroom is shown, featuring a bathtub with a shower. Light-colored tiles accent the walls. White towels are neatly hung on a rack, and a framed black-and-white photo adds a decorative touch. A small window provides natural light.

Home in Hyde Park

4.85 out of 5 average rating, 217 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Top guest favorite

A resting fawn is positioned on lush green grass, surrounded by a wire fence. The fawn's spotted coat is visible as it curls up peacefully, blending softly into the natural setting.

Guest suite in Marlboro Township

4.97 out of 5 average rating, 472 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Superhost

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

4.86 out of 5 average rating, 189 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top guest favorite

A keyless entry keypad is mounted on a light-colored wall, featuring a sleek black design with numerical buttons. The device provides a modern solution for contactless access to the apartment.

Apartment in New Paltz

4.99 out of 5 average rating, 145 reviews

Escape To The Gunks! Very close to climbing routes

Located in the heart of the Shawangunk Mountains or the Gunks, home to some of the best rock climbing, also just minutes away you could be swimming at Lake Minnewaska or shopping in the village of New Paltz. Biking is an option right from your front door! This second-story apartment is perfect for a couple plus a sofa sleeper can accommodate another 2 people. If you appreciate the sounds of nature on the back deck or enjoy cooking in the modern kitchen, we hope you'll stay with us!

Top guest favorite

A wooden deck with natural wood finishes features lounge chairs positioned for relaxation, overlooking a grassy area. Sunlight filters through the trees, creating a serene outdoor space. Yellow flowers bloom near the base of the deck, enhancing the natural setting.

Guest suite in Ulster Park

4.94 out of 5 average rating, 115 reviews

Sunny and Spacious Studio - a serene getaway

Modern Light Filled Garage Conversion with a small kitchen, full bath with an open deck off the back. A beautiful quiet spot with birds, tall trees and a small creek on 3 acres. The bedroom has a comfortable Queen bed with a small ladder to a little sleeping loft for the kids. There is also a pull out couch in the open kitchen living room area with a deck off the back. This is a small apartment attached to our house that has been designed with care and privacy in mind.

Guest favorite

Apartment in Highland

4.9 out of 5 average rating, 389 reviews

New Paltz 19th cent. Restored Barn - North Hayloft

One of two beautifully appointed loft apartments in a 19th century Barn Hayloft! Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only 10 minutes from New Paltz and set back on a lightly traveled road for long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station! And book the South Hayloft here https://www.airbnb.com/rooms/41910407 to sleep a total of 10 guests!

Top guest favorite

A cozy corner of the tiny house is depicted, featuring a bench with plush cushions. Natural light enters through two windows adorned with sheer white curtains, illuminating the wooden walls and adding warmth to the space.

Tiny home in New Paltz

4.99 out of 5 average rating, 826 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 316 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

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Popular amenities for Highland vacation rentals

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Other great vacation rentals in Highland

Top guest favorite

A modern kitchen corner features a Keurig coffee maker alongside a selection of coffee pods arranged in a tray. A pale pink vase holds delicate flowers, and a woven basket contains snacks, creating an inviting space for preparing morning beverages.

Apartment in Clintondale

5 out of 5 average rating, 30 reviews

Cozy Cottage Getaway in Clintondale Near New Paltz

SankalpRating, 5 stars6 days ago

5 stars all the way. The location, the interiors, the equipment, linens, provisions were all top notch. Nick and Mar were generous and responsive hosts. One of the best stays I’ve had!

Guest favorite

A fire pit, surrounded by log seating, emits a warm glow in a natural setting. Green foliage and trees provide a serene backdrop, while the evening sky transitions to dusk, enhancing the peaceful atmosphere of the outdoor space.

Home in Pleasant Valley

5 out of 5 average rating, 27 reviews

The Wildflower House

MatthewRating, 5 stars1 month ago

Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

Top guest favorite

A charming exterior view of the apartment showcases a white wood-paneled building framed by blooming pink trees. The front porch features a small seating area, while the surrounding greenery adds a touch of nature to the setting.

Apartment in Poughkeepsie

4.98 out of 5 average rating, 66 reviews

Charming Getaway in Historic Poughkeepsie

ElizabethRating, 5 stars1 week ago

This was a wonderful, comfortable apartment with a nice backyard area, close to the train station and a very short drive to Vassar College. A lovely spot to enjoy exploring the Hudson Valley from! The hosts are communicative, had a bottle of wine waiting for us, and everything was very clean. They were also kindly flexible about adjusting our check in time. Thank you for a great stay!

Guest favorite

An outdoor area is featured, illuminated by string lights overhead. A hot tub is positioned under a shelter with slatted roofing, surrounded by wooden fencing for privacy. The paved floor offers a clean and spacious setting for relaxation.

Home in Highland

4.9 out of 5 average rating, 42 reviews

Beautiful Home - 4BR/2.5BA - Hot Tub and Patio

EvanRating, 5 stars5 days ago

This was a beautiful home in a great location! The home was very clean and the hosts were very responsive and flexible with us when an unexpected situation arose with our car!

Guest favorite

A serene riverside view showcases still waters reflecting a clear blue sky. A modern bridge spans across the river, with mountains visible in the distance. The waterfront path is lined with rocks, and trees provide gentle shade along the edge.

Apartment in Poughkeepsie

4.93 out of 5 average rating, 30 reviews

Sunny Apartment in Historic Home

SageRating, 5 stars2 weeks ago

I had a very nice stay at Heather's place! The apartment was lovely and a comfortable place to spend time between different activities in Poughkeepsie. Very walkable to the convention center and to a main drag with restaurants and coffee shops. Definitely recommend and would stay there again if I found myself in the area!

Superhost