
Vacation rentals in Highlands
Find and book unique accommodations on Airbnb
Top-rated vacation 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 Loft Morning Muffin Basket
Book with me if you want exceptional quality in a homey safe & secure environment. Do you want- - 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 - Parking at door. - Writing desk. - Wifi - Singles/double Minutes from -SKAC -USMA -Woodbury Common -Stewart Airport -Beacon-DIA-Metro -No cooking allowed. Inquire about extra guests. Relax. Enjoy. Book now.

Serene Victorian Guest Apartment with Clawfoot Tub
Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

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!

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.

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.

Haverstraw Hospitality Suite
Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

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.

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 vacation rentals
Other great vacation rentals in Highlands

Private, modern carriage house. Great for couples.

Billie's Room in Beacon 1794 Home Walk 2 Train

Burr House at Sweet Clover Farm

Peaceful Forest Cabin

Fairytale Stone Cabin | Garrison

West Point Cottage

Little haven by the woods

Modern, sun-filled farmhouse retreat
When is the best time to visit Highlands?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ716 | ﺩ.ﺇ690 | ﺩ.ﺇ735 | ﺩ.ﺇ815 | ﺩ.ﺇ933 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ852 | ﺩ.ﺇ856 | ﺩ.ﺇ830 |
| 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 house rentals in Highlands have a kitchen?
Absolutely! We offer over 100 house rentals with a kitchen in Highlands. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Highlands have free parking?
Absolutely! We offer over 10 hotel 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 wifi, over 40 homes with a kitchen, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Highlands have wifi?
Absolutely! We offer over 110 house rentals with wifi in Highlands. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Highlands have air conditioning?
Absolutely! We offer over 100 house 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 vacation rentals in Highlands

Total vacation rentals
Explore 210 vacation rentals in Highlands

Nightly prices starting at
Highlands vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 14,210 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wi-Fi availability
210 of Highlands vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highlands rentals

4.9 Average rating
Highlands stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Fitness-friendly rentals Highlands
- Rentals with a fireplace Highlands
- Rentals with breakfast Highlands
- Rentals with pools Highlands
- Rentals with a patio Highlands
- Rentals with outdoor seating Highlands
- Rentals with a fire pit Highlands
- Family-friendly rentals Highlands
- Apartment rentals Highlands
- Hotel rooms Highlands
- Waterfront rentals Highlands
- Rentals with a washer and dryer Highlands
- Pet-friendly rentals Highlands
- House rentals Highlands
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library Main Branch
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Radio City Music Hall
- Statue of Liberty
- Canarsie Beach
- Rye Beach
- USTA Billie Jean King National Tennis Center
- McCarren Park
- The Metropolitan Museum of Art
- Astoria Park
- Thunder Ridge Ski Area




