Holiday houses in Highlands

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Top-rated holiday rentals in Highlands

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

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Top Guest favourite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley
4.99 out of 5 average rating, 138 reviews

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

Guest favourite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.84 out of 5 average rating, 602 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Guest favourite
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Apartment in Newburgh
4.84 out of 5 average rating, 346 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Top Guest favourite
A cozy room with a small kitchenette and a dining area featuring a round table and two chairs. Natural light fills the space through a glass door, which leads to the side yard. A minimalist wall art piece adds a touch of character to the room.
Guest suite in Beacon
4.97 out of 5 average rating, 330 reviews

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

Top Guest favourite
The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.
Guest suite in New Windsor
4.95 out of 5 average rating, 258 reviews

Artistic Loft Quality. Privacy. Morning muffins.

Features - Hotel quality in a homey atmosphere - 2 Super comfy queen sized beds. - Huge bathroom - Heated Jacuzzi bathtub - Seated shower -Coffee/Tea/Morning Muffins - Kitchenette refrigerator - microwave- Keurig - tea kettle - Coffees, teas, morning muffins - Private driveway. Parking at door. - Dedicated work desk. Wifi - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -Must be 25 years or older to book. No parties. - dbl occ

Superhost
Barn in Mountainville
4.94 out of 5 average rating, 134 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.

Top Guest favourite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 196 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Guest favourite
A cozy studio space includes a queen bed with a light-colored coverlet. A kitchenette features essential appliances, complemented by a dining area with wooden table and black chairs. A flat-screen TV is mounted on the wall, and natural light brightens the room.
Guest suite in Mountainville
4.94 out of 5 average rating, 137 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
A spacious bedroom features a comfortable bed with soft linens, complemented by bedside lamps. Large windows offer views of the surrounding greenery and mountains. An outdoor deck extends into the natural landscape, furnished with lounge chairs, inviting relaxation amid scenic surroundings.
Loft in Mountainville
4.97 out of 5 average rating, 146 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.

Top Guest favourite
The exterior of the home is framed by green grass and colorful landscaping, featuring a stone wall and blooming yellow flowers in the foreground. Tall trees provide shade, while a clear sky with fluffy clouds creates a bright and inviting atmosphere.
Home in Highland Falls
4.98 out of 5 average rating, 108 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.

Guest favourite
A modern kitchen area features sleek blue cabinetry complemented by a stainless steel refrigerator. A white countertop provides workspace above a stainless sink, with a dish rack nearby. The floor is adorned with a textured gray surface, contributing to the kitchen's contemporary feel.
Apartment in Nelsonville
4.86 out of 5 average rating, 181 reviews

Wooded stream side Retreat

Small basement apartment nestled in the village of Cold Spring, within walking distance to Main Street (10 minutes) and train (15-20 min). Apartment borders a wooded stream that leads to the old foundry and the Hudson River. Plenty of hiking nearby. Ample parking in driveway. Privacy.

Top Guest favourite
A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.
Home in New Windsor
4.92 out of 5 average rating, 140 reviews

View House

Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

Popular amenities for Highlands holiday rentals

When is the best time to visit Highlands?

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Avg. price$298 AUD$288 AUD$306 AUD$340 AUD$389 AUD$383 AUD$383 AUD$383 AUD$383 AUD$355 AUD$356 AUD$346 AUD
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Frequently Asked Questions

  • Do apartment rentals in Highlands have a kitchen?

    Absolutely! We offer over 40 apartment rentals with a kitchen in Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Highlands have free parking?

    Absolutely! We offer over 30 apartment rentals with free parking in Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Highlands?

    Highlands has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Highlands?

    Yes! Work meets play with ease at over 110 vacation rentals in Highlands featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Highlands?

    Four-legged friends are welcome in Highlands. Choose from more than 80 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for Hotel Rentals in Highlands?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do private suite rentals in Highlands have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Highlands have air conditioning?

    Absolutely! We offer over 10 private suite rentals with air conditioning in Highlands. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Highlands?

    Experience the best of Highlands with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Highlands vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Highlands, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about holiday rentals in Highlands

  • Total holiday rentals

    Explore 210 holiday rentals in Highlands

  • Nightly prices starting at

    Highlands holiday rentals start at $77 AUD per night before taxes and fees

  • Verified guest reviews

    Over 14,210 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Highlands holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Highlands rentals

  • 4.9 Average rating

    Highlands stays are highly rated by guests—averaging 4.9 out of 5!

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