Vacation rentals in Highlands

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Top-rated vacation rentals in Highlands

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Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep 27 – Oct 4

G$28,238 GYD per night

Guest favorite

Apartment in Philipstown

4.88 out of 5 average rating, 187 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Sep 24 – Oct 1

G$27,851 GYD per night

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Oct 4 – 11

G$115,042 GYD per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Feb 22 – Mar 1

G$22,211 GYD per night

Guest favorite

Guest suite in Cold Spring

4.79 out of 5 average rating, 482 reviews

Cozy getaway in Cold Spring

Sweet studio attached to our house w/updated kitchen & bathroom on a dead-end street backed up to a nature preserve. We have parking for those arriving by car & are a block from the train if coming up from the city. Walking distance to everything (Main St is 2 blocks away!) We welcome all types of folks and your lovely pets as well. We're here for your needs & offer as much contact or privacy as you like! In the summer, an outdoor shower is available to you as well through the backyard.

Dec 21 – 28

G$31,476 GYD per night

Guest favorite

Guest suite in Beacon

4.97 out of 5 average rating, 289 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.

May 28 – Jun 4

G$21,518 GYD per night

Guest favorite

Apartment in New Windsor

4.95 out of 5 average rating, 112 reviews

Private/Spacious Studio. Guest Loyalty Program

LOYALTY PROGRAM for repeat bookings. $30 off of your second night stay ((dbl occ rates and extra guest fees apply) OR a 3rd guest stays free with your one night stay. Discount will be applied upon your inquiry. - Perfect location for your West Point visit. - SKAC -Woodbury Common Sleeps up to six guests comfortably. Safe/secure - Perfect for single travelers Parking at door for several vehicles Coffee/Tea/Keurig Close to restaurants, NYS Thruway, Routes 9W

Dec 7 – 14

G$25,661 GYD per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

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:)

Feb 18 – 25

G$17,622 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Nov 26 – Dec 3

G$25,907 GYD per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 393 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside 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 flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Mar 7 – 14

G$18,985 GYD per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 reviews

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

Oct 28 – Nov 4

G$27,401 GYD per night

Guest favorite

Farm stay in Fort Montgomery

4.97 out of 5 average rating, 148 reviews

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.

Jul 21 – 28

G$52,195 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Highlands vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Highlands's top sights

The Thayer Hotel15 locals recommend

United States Military Academy58 locals recommend

Bear Mountain Inn and Overlook Lodge16 locals recommend

West Point Academy60 locals recommend

Bear Mountain Pool5 locals recommend

Anthony Wayne Recreation Area3 locals recommend

Other great vacation rentals in Highlands

Guest favorite

Tiny home in Cold Spring

5.0 out of 5 average rating, 239 reviews

Tiny house on tiny farm close to hiking trails.

Jul 7 – 14

G$28,992 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Feb 9 – 16

G$27,376 GYD per night

Guest favorite

Home in Highland Falls

4.99 out of 5 average rating, 141 reviews

Spacious, bright 5 bedroom house near West Point

Sep 9 – 16

G$91,661 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 741 reviews

Hudson Valley Tiny House

Jul 5 – 12

G$22,915 GYD per night

Guest favorite

Apartment in Highland Falls

4.84 out of 5 average rating, 98 reviews

Cozy 1-bedroom retreat minutes from West Point!

Nov 11 – 18

G$23,326 GYD per night

Guest favorite

Guest suite in Highland Falls

4.94 out of 5 average rating, 32 reviews

Modern place with private gated parking.

Jan 19 – 26

G$24,868 GYD per night

Guest favorite

Home in Highland Falls

4.98 out of 5 average rating, 42 reviews

Luxury Home Near West Point

Apr 10 – 17

G$28,390 GYD per night

Guest favorite

Condo in Highland Falls

4.96 out of 5 average rating, 85 reviews

❤️😍 Cozy studio apartment in quiet neighborhood 🥰❤️

Apr 11 – 18

G$28,712 GYD per night

Show all

Quick stats about vacation rentals in Highlands

Total rentals
200 properties
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
11K reviews

Frequently Asked Questions

Do apartment rentals in Highlands have a kitchen?
Absolutely! We offer over 20 apartment rentals with a kitchen in Highlands. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Highlands have free parking?
Absolutely! We offer over 100 house 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 120 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 90 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 60 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 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do hotel rentals in Highlands have wifi?
Absolutely! We offer over 10 hotel 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 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 20 vacation homes with pools in Highlands, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Highlands

Top-rated vacation rentals in Highlands

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Highlands vacation rentals

Stay near Highlands's top sights

Other great vacation rentals in Highlands

Tiny home in Cold Spring

Home in New Paltz

Home in Highland Falls

Tiny home in New Paltz

Apartment in Highland Falls

Guest suite in Highland Falls

Home in Highland Falls

Condo in Highland Falls

Quick stats about vacation rentals in Highlands

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do apartment rentals in Highlands have a kitchen?

Do house rentals in Highlands have free parking?

Are there family-friendly vacation rentals in Highlands?

Are there vacation rentals with a dedicated workspace in Highlands?

Are there pet-friendly vacation rentals in Highlands?

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

Do hotel rentals in Highlands have wifi?

Do private suite rentals in Highlands have air conditioning?

How much does it cost to stay in hotel rentals in Highlands?

Are there Highlands vacation rentals on Airbnb with pools?

Destinations to explore