
Holiday houses 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.

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. We live here with kids/dogs so you may hear us moving

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.

Sunny Artistic Loft Morning Muffins Clean &Comfy
Exceptional quality - safe & secure environment. Perfectly located for- -Storm King Art Center -USMA - Woodbury Common - DIA Beacon - Morning muffins/cookies - Coffee bar, teas, hot cocoa - 2 Super comfy queen sized beds. - Huge bathroom - Heated Jacuzzi bathtub - Seated shower - Private driveway. Private entrance. Park at door. - Writing desk. - Wifi - Singles/double -Local hiking -Historical sights -Vineyards -No cooking allowed. Inquire about extra guests. Relax. Enjoy. Book now.

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.

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!

Historic 1 bedroom home in Cold Spring, NY
This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

Ela - a 1 Bed Escape, Washer/Dryer in Unit
Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.

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.

Peekskill Carriage House Downtown Studio
Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Secluded overlook cottage near West Point
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 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.

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.

Beautiful loft space
Located in the heart of Cold Spring, NY, this beautiful architect-designed loft space is only 2 blocks away from the Metro North train stop. It features a large single bedroom, a full kitchen, a full dining table and chairs, and a sleeper sofa.
Popular amenities for Highlands holiday rentals
Other great holiday rentals in Highlands

Gorgeous Suite w/ Private Entrance

Highland Falls Home - 1/2 Mile to West Point

Maple Ridge Retreats - Apt B

Billie's Room in Beacon 1794 Home Walk 2 Train

2bd/1bath near West Point in fmr JP Morgan estate!

Private Apartment in 1820’s Cottage - New Reno

Arkadia House Mid-century retreat with pool & view

Cornwall on Hudson Private Apartment
When is the best time to visit Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $292 AUD | $281 AUD | $299 AUD | $332 AUD | $380 AUD | $374 AUD | $374 AUD | $374 AUD | $374 AUD | $347 AUD | $349 AUD | $338 AUD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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 Apartment Rentals in Highlands?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with free parking, over 40 homes with a kitchen, over 40 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Highlands have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Highlands. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Highlands have air conditioning?
Absolutely! We offer over 20 hotel rentals with air conditioning in Highlands. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in hotel rentals in Highlands?
Experience the best of Highlands with our hotel rentals, starting at about $130 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Apartment rentals Highlands
- Rentals with a fireplace Highlands
- Rentals with pools Highlands
- Family-friendly rentals Highlands
- Rentals with a washing machine and dryer Highlands
- Pet-friendly rentals Highlands
- Fitness-friendly rentals Highlands
- Hotel rooms Highlands
- Waterfront rentals Highlands
- Rentals with a fire pit Highlands
- Rentals with a patio Highlands
- Rentals with outdoor seating Highlands
- House rentals Highlands
- Rentals with breakfast Highlands
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Grand Central Terminal
- New York Public Library Main Branch
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Empire State Building
- Fairfield Beach
- Radio City Music Hall
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- The Metropolitan Museum of Art
- Thunder Ridge Ski Area
- Astoria Park
- One World Trade Center
- Bronx Zoo
- Minnewaska State Park Preserve




