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Highland, NY place to stay
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38 Lodgings in Highland, NY

Best family friendly Highland, NY lodging

Among the 38 accommodations in Highland, NY, here are the 4 best for families

The Gatehouse In Historic Hyde Park - Highland, NY
10 112 reviews

The Gatehouse In Historic Hyde Park

apartment, Hyde Park
This charming apartment is located on the edge of the 211-acre Vanderbilt Estate in Hyde Park, just a short drive from the Franklin D. Roosevelt Presidential Library and Museum. It benefits from excellent user, location and cleanliness ratings, making it a popular choice for visitors to the area.
The property, which can accommodate up to six guests, offers three bedrooms and two bathrooms. Guests can enjoy a range of amenities including a gourmet kitchen, a garden with outdoor games, a fitness centre, ample parking and a keyless entry system.
Rustic Hudson R. Home With Firepit/bar/billiard - Highland, NY
9.8 166 reviews

Rustic Hudson R. Home With Firepit/bar/billiard

apartment, Hyde Park
This Hyde Park apartment is situated on the first floor of a building, just a short walk from the lakefront and a 2-kilometre drive from the University of Chicago. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious and can accommodate up to 5 guests. It features a unique rustic design with a large entertainment area, a private patio with a fire pit, and a fully equipped kitchenette. Guests can enjoy a billiard/pong combo table, multiple TVs, laundry facilities, and access to outdoor spaces.
Black Walnut Tree Farm: 50-acres + Private Pond - Highland, NY
9.6 5 reviews

Black Walnut Tree Farm: 50-acres + Private Pond

apartment, Clintondale
This Highland countryside farmhouse, a 33-minute (53km) drive from Mohonk Lake and 12-minute (19km) drive from the Walkway Over the Hudson State Historic Park, offers a convenient rural location near major attractions.
Sleeping up to eight guests, the property boasts three bathrooms, a fully equipped kitchen including dishwasher and microwave, Wi-Fi, laundry facilities, a private garden, and barbecue facilities, all within easy reach of Quartz Rock Vineyard and Franny Reese State Park.
Our Home Is Perfect For Relaxing And Having Lots Of Fun, With Near By Activitys - Highland, NY
9.6 12 reviews

Our Home Is Perfect For Relaxing And Having Lots Of Fun, With Near By Activitys

apartment, Clintondale
This spacious apartment is located in Highland, just a short drive from Clintondale and within easy reach of Vassar Hospital and Marist College. The property is situated in a peaceful residential area, perfect for a relaxing getaway.
The apartment offers four bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Amenities include a well-equipped kitchen, a welcoming living area with a fireplace, a private backyard with a fire pit, and modern conveniences such as Wi-Fi, air conditioning, and a Jacuzzi.

Best Highland, NY lodging with a pool

Among the 38 accommodations in Highland, NY, here are the 4 best ones with a pool

Hudson Riverfront Retreat - Highland, NY
9.2 27 reviews

Hudson Riverfront Retreat

apartment, Hyde Park
This luxurious eight-bedroom Hyde Park apartment boasts a stunning riverfront location with a private beach, situated approximately 16 kilometres from New Paltz, Kingston, and Poughkeepsie.
Sleeping up to 18 guests comfortably in 13 beds, this self-catering property features a dishwasher, air conditioning, a swimming pool, jacuzzi, sauna, parking, and is within walking distance of the Hudson House Distillery and a local winery.
S'mores Studio Hideaway - Highland, NY
10 5 reviews

S'mores Studio Hideaway

apartment, Highland
This Highland studio apartment is located near John Burroughs’ Slabsides and Nature Sanctuary, the Walkway Over the Hudson, several wineries, and an apple orchard.
This pet-friendly studio offers accommodation for two guests, featuring a private swimming pool, an outdoor gas grill, a firepit, in-unit laundry, and central air conditioning, with exclusive use of the outdoor amenities while the owner resides on the property.
Secluded House On 55 Ac W/pool 5 Mins To New Paltz - Highland, NY
10 2 reviews

Secluded House On 55 Ac W/pool 5 Mins To New Paltz

apartment, Highland
This apartment is located on 55 acres of meadows and woodland, approximately 5 minutes by car from the centre of New Paltz, New York.
This property accommodates up to six guests in three bedrooms, offering a private outdoor swimming pool, a well-equipped kitchen, and laundry facilities.
Artistic Oasis Near New Paltz - Highland, NY
No reviews

Artistic Oasis Near New Paltz

apartment, New Paltz
This three-bedroom, two-bathroom flat, accommodating up to six guests, offers a tranquil escape just 8 kilometres from New Paltz village, providing convenient access to Kingston, Woodstock, and the Walkway over the Hudson.
Guests can enjoy a private swimming pool, garden, and parking, alongside essential amenities such as a fridge, air conditioning, and Wi-Fi, making this a well-equipped base for exploring the Hudson Valley.

Frequently asked questions about accommodations in Highland, NY

  • What outdoor activities can visitors enjoy in and around Highland, NY?

    Highland is a haven for outdoor enthusiasts! Hiking, biking, and kayaking are all popular activities. You can explore the trails of the Shawangunk Ridge, go for a swim in Lake Minnewaska, or rent a kayak on the Hudson River.
  • When is the ideal time to plan a trip to Highland, NY?

    Spring and autumn are the most pleasant times to visit Highland, with mild temperatures and vibrant foliage. Summer can be hot and humid, while winter brings snow and cold temperatures, making it perfect for skiing and snowboarding.
  • What are the best walking or cycling routes in Highland, NY?

    The Overlook Mountain Trail is a popular hike with stunning views of the surrounding area. For a more leisurely stroll, try the Walkway Over the Hudson, a pedestrian bridge spanning the Hudson River. Cyclists will enjoy the Wallkill Valley Rail Trail, a paved path that follows the old rail line.
  • What nearby towns or cities can be explored from Highland, NY?

    New Paltz, a charming college town with a vibrant arts scene, is just a short drive away. Poughkeepsie, a larger city with a historic downtown and the Vassar College campus, is also worth exploring. And of course, you can easily get to New York City for a day trip.
  • What amenities can travelers expect from accommodations in Highland, NY?

    Highland offers a range of accommodations, from cozy bed and breakfasts to spacious hotels. Many accommodations offer amenities like swimming pools, fitness centers, and on-site restaurants. You can also find cabins and vacation rentals in the surrounding area.

Popular destinations

Best Highland, NY accommodations with a garden

Charming Brick House -Hudson Valley - Highland, NY
9.9 148 reviews

Charming Brick House -Hudson Valley

apartment, Haviland
This charming house, situated just a short drive from the Culinary Institute of America in Poughkeepsie/Hyde Park, offers a peaceful retreat with its secluded location across from a wooded area. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house, spanning 186 square metres, boasts three bedrooms and a bathroom, providing ample space for families or groups. Guests can enjoy a well-equipped kitchen, a private garden, a terrace, and a range of amenities including Netflix, Hulu, and an Apple TV, along with a washer and dryer.
Splendid Isolation @ Extraordinary Country Retreat - Highland, NY
9.9 153 reviews

Splendid Isolation @ Extraordinary Country Retreat

apartment, Highland
This stunning private residence is located on a peninsula overlooking the Hudson River in Highland, just 1.5 hours from New York City and a short drive from FDR's Birthplace & Summer White House. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The villa spans 381 square metres and can accommodate up to eight guests in its four bedrooms. The property offers a wide range of amenities and activities, including a heated saltwater pool, a tennis court, a hot tub, a gourmet kitchen, a 10' screen media room, a huge deck, a screened porch, Jacuzzis, steam showers, a sauna, and a private sculpture garden.
Fully Renovated Loft Apartment 
Permit # 20240329 - Highland, NY
10 34 reviews

Fully Renovated Loft Apartment Permit # 20240329

apartment, Fairview
This Fairview apartment is conveniently located within walking distance of Marist College, the Culinary Institute of America, and the Walkway Over the Hudson, offering easy access to these popular attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom flat comfortably accommodates up to four guests. The apartment is well-equipped with amenities including a fully fitted kitchen, a games room with a fireplace, and a garden, providing everything needed for a comfortable stay.
Wooded Rhinebeck-beacon Area Escape W/outdoor Spa - Highland, NY
10 80 reviews

Wooded Rhinebeck-beacon Area Escape W/outdoor Spa

apartment, Fairview
This Fairview apartment is situated in Hyde Park, New York, just a short drive from Poughkeepsie and Rhinebeck, making it a great base for exploring the Hudson Valley. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is a comfortable and spacious property with two bedrooms, sleeping up to four guests. It offers a range of amenities, including a hot tub, a fully equipped kitchen, and a screened-in porch, perfect for relaxing after a day of exploring the local attractions.

Best Highland, NY accommodations with a kitchen

Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Highland, NY
9.5 4 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

house, Hyde Park
This Hyde Park holiday home is conveniently located near the Bardavon 1869 Opera House (10.3 km) and SUNY New Paltz (13.5 km), offering easy access to both cultural attractions and the scenic Highland hiking trails.
This recently renovated four-bedroom property boasts a fully equipped kitchen in each unit, private parking, air conditioning, a terrace, garden, and barbecue facilities, ideal for families seeking a comfortable stay.
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Highland, NY
10 25 reviews

Spacious 4bd Country Gem - Fire Pit & Chill Vibes

apartment, Hyde Park
This Highland holiday home, situated in a rural setting within 9.6km of the Walkway Over the Hudson State Historic Park, Berean Park Beach, and the Franklin D. Roosevelt Presidential Library and Museum, offers a tranquil escape near popular attractions.
This 278 square metre property boasts four bedrooms, four bathrooms, and sleeps eight, featuring a fully equipped kitchen, private balcony, garden, parking, and free Wi-Fi.
The Scenic Mansion With Breathtaking View - Highland, NY
8.0 21 reviews

The Scenic Mansion With Breathtaking View

house, Highland
This luxurious Milton mountain villa boasts stunning views, situated 1.8km from Franny Reese State Park and under 5km from the Hudson River and Walkway Over the Hudson State Historic Park.
Sleeping up to 10 guests, this four-bedroom, six-bathroom property offers a private pool, tennis court, and ample amenities including a fully equipped kitchen, fireplace, and jetted tub, perfect for a family holiday near Berean Park Beach (5km).
The Hudsy Home - Highland, NY
9.8 111 reviews

The Hudsy Home

apartment, Fairview
This Poughkeepsie flat, in Fairview, offers easy access to the Walkway Over the Hudson (less than 1km away) and is a short drive (around 3.2km) from Vassar and Marist Colleges.
The self-catering suite comprises one bedroom, one bathroom, sleeps two guests, includes a 65-inch TV, designated parking, and a full kitchen with fridge, freezer and microwave; nearby amenities include Starbucks, Chipotle, CVS and ShopRite.
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