Vacation rentals in Highlands

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Popular amenities for Highlands vacation rentals

Other great vacation rentals in Highlands

Top guest favorite
Guesthouse in Philipstown
4.99 out of 5 average rating, 97 reviews

Historic 1 bedroom home in Cold Spring, NY

AmyRating, 5 stars5 days ago
My husband and I stayed 2 nights for our anniversary and loved it! Pieter and Jackie were lovely people, and the place is even better than the photos. We had everything we needed, and while we had a car we didn't use it because it was so easy to walk everywhere - a hiking trail, restaurants, shops, the waterfront! We would definitely stay here again!
Top guest favorite
Home in Cornwall
4.98 out of 5 average rating, 44 reviews

Sunset House: near West Point, Hiking & Woodbury

CamilleRating, 5 stars1 month ago
Our family stayed here for my son's West Point graduation. This was our second visit and we were thrilled to be back. This house is well taken care of, clean, and relaxing. It's close to the town of Cornwall, grocery stores, etc so you have access to what you need. The hosts are responsive, helpful and welcoming. Highly recommend!
Guest favorite
Apartment in Cornwall-on-Hudson
4.98 out of 5 average rating, 58 reviews

Cornwall on Hudson Private Apartment

MariaRating, 5 stars1 month ago
Very comfortable stay with all the comforts of home. Very conveniently located near hiking trails, Hudson River and great restaurants. Will definitely return!
Guest favorite
Home in Fort Montgomery
4.92 out of 5 average rating, 37 reviews

West Point Cottage

SamanthaRating, 5 stars4 weeks ago
My partner and I booked Philomena and Derek’s place for Memorial Day wknd to attend a wedding at West Point. It was the perfect location and a cute space. We went to dinner at a restaurant nearby called the Bird and Bottle Inn which was also great.
Guest favorite
Apartment in New Windsor
4.96 out of 5 average rating, 23 reviews

The Bluebird at Storm King Lodge.

StephanieRating, 5 stars1 month ago
Exactly as pictures describe. If you arrive early and wish to leave belongings we were able to use the covered garage. The shower was excellent - almost could create a mini steam room. Outdoor space idyllic. Cary communicated very well and we have no complaints! Would recommend.
Guest favorite
Guest suite in Highland Falls
4.94 out of 5 average rating, 64 reviews

Modern place with private gated parking.

ToniRating, 5 stars3 weeks ago
Doris’s place was very clean and the bed was comfortable. The place is tastefully designed. Nice towels and amenities. I would stay again.
Guest favorite
Home in Cortlandt
4.9 out of 5 average rating, 21 reviews

Lovely cottage, ideal location

JohnRating, 5 stars6 months ago
Had an amazing stay, would highly recommend to anyone looking for a nice quiet place to stay for a weekend getaway.
Top guest favorite
Apartment in Highland Falls
4.87 out of 5 average rating, 87 reviews

Gateway to West Point.

BennettRating, 5 stars4 months ago
I have stayed in a number of places in Highland Falls over the past several years. Robert’s listing is unquestionably the best air bnb listing in town. Right next to the gate, clean, and homey. Robert was an amazingly responsive host and was flexible with my check in/check out times. A great spot to stay, particularly for any USMA-related events!

Quick stats about vacation rentals in Highlands

  • Total rentals

    210 properties

  • Total number of reviews

    13K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

Frequently Asked Questions

  • Do house rentals in Highlands have a kitchen?

    Absolutely! We offer over 110 house 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 110 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 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 100 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 70 vacation rentals for guests traveling with pets.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with free parking, over 110 homes with wifi, over 110 homes with air conditioning, over 110 homes with a kitchen, 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 private suite rentals in Highlands?

    Experience the best of Highlands with our private suite 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 house rentals on Airbnb with pools?

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

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