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

Jul 6 – 13

R2,736 ZAR per night

Guest favorite

Farm stay in Fort Montgomery

4.94 out of 5 average rating, 198 reviews

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" 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 mins from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Enjoy fresh eggs every morning or vegetables from our organic garden (during season). Come, relax by the outdoor fire pit, fish or hike/explore the forest trails right out the front door.

Aug 9 – 16

R5,996 ZAR per night

Superhost

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.

Aug 6 – 13

R2,653 ZAR 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.

Mar 7 – 14

R2,042 ZAR per night

Superhost

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Jan 12 – 19

R2,454 ZAR 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.

Jan 31 – Feb 7

R2,870 ZAR 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

Newly renovated 5 bedroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Sep 29 – Oct 6

R8,820 ZAR 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:)

Jan 17 – 24

R1,607 ZAR per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 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 14 – 21

R2,380 ZAR per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 390 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!

Oct 15 – 22

R1,731 ZAR 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

R2,498 ZAR per night

Guest favorite

Apartment in New Windsor

4.95 out of 5 average rating, 110 reviews

Quiet/Private/Spacious Studio. Balcony. Parking.

-Perfect location for West Point visitors. Quiet. Private. Bring the family! Sleeps up to six guests comfortably. -Visit SKAC -Shop Woodbury Common Safe/secure - Perfect for single travelers Parking at door for several vehicles Coffee/Tea/Keurig Close to restaurants, NYS Thruway, Routes 9W

Dec 2 – 9

R2,343 ZAR 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

Apartment in Cold Spring

4.87 out of 5 average rating, 171 reviews

Charming Apartment in the Heart of Cold Spring

Aug 30 – Sep 6

R2,511 ZAR per night

Guest favorite

Home in Highland Falls

4.95 out of 5 average rating, 170 reviews

Luxury home near West Point

Jan 31 – Feb 7

R9,307 ZAR per night

Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 418 reviews

Garden View Guest Cottage

Dec 10 – 17

R2,452 ZAR 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!

Mar 9 – 16

R2,127 ZAR per night

Guest favorite

Guest suite in Highland Falls

4.94 out of 5 average rating, 32 reviews

Modern place with private gated parking.

Feb 3 – 10

R2,267 ZAR per night

Guest favorite

Loft in Mountainville

4.97 out of 5 average rating, 76 reviews

Lovely, Quiet and Very Private! Entire Loft!

Jan 7 – 14

R3,237 ZAR per night

Superhost

Cottage in Cornwall

4.88 out of 5 average rating, 24 reviews

Cozy Cottage near Hiking and Storm King

Jul 9 – 16

R3,106 ZAR per night

Guest favorite

Condo in Highland Falls

4.96 out of 5 average rating, 83 reviews

❤️😍 Cozy studio apartment in quiet neighborhood 🥰❤️

Sep 11 – 18

R2,922 ZAR 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 private suite rentals in Highlands have free parking?
Absolutely! We offer over 10 private suite 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 Private Suite Rentals in Highlands?
Enhance your stay in our Private Suite 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 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 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

Apartment in Cold Spring

Home in Highland Falls

Guest suite in Montgomery

Apartment in Highland Falls

Guest suite in Highland Falls

Loft in Mountainville

Cottage in Cornwall

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 private suite 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 Private Suite Rentals in Highlands?

Do private suite 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