Town of Highlands Holiday Rentals

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Our top choices for Town of Highlands holiday rentals

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is NZ$1,058
includes taxes & fees
2 June - 3 June
Updated Home w/ Patio Half Mile to West Point

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is NZ$557
includes taxes & fees
27 May - 28 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$656
includes taxes & fees
26 May - 27 May
House on the Babbling Brook- Quiet 2BR + King Bed!

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$380
includes taxes & fees
27 May - 28 May
Cozy 1-bedroom retreat minutes from West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is NZ$521
includes taxes & fees
26 May - 27 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"Very nice apartment in Highland Falls. Each bedroom has nice closet space and the master is very large. Remodeled very well and comfortable. "
United States
chris f.
The price is NZ$763
includes taxes & fees
27 May - 28 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is NZ$613
includes taxes & fees
27 May - 28 May
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is NZ$552
includes taxes & fees
16 June - 17 June
Luxury House Near West Point

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is NZ$924
includes taxes & fees
25 May - 26 May
3BR West Point Retreat-3min to Back Gate+ King Bed

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is NZ$746
includes taxes & fees
27 May - 28 May
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is NZ$714
includes taxes & fees
27 May - 28 May
Fabulous 3bdrm Home w/parking!

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (16 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is NZ$782
includes taxes & fees
27 May - 28 May
Local Artist Inspired | Walk to WestPoint + King Bed

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is NZ$826
includes taxes & fees
7 June - 8 June
Luxury home near West Point

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (23 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is NZ$694
includes taxes & fees
27 May - 28 May
Walk to WP Gate + Free Parking!

Luxury Townhouse Near West Point

Luxury Townhouse Near West Point
Highland Falls
The price is NZ$631
includes taxes & fees
25 May - 26 May
Luxury Townhouse Near West Point

Luxury Home Near West Point

Luxury Home Near West Point
Highland Falls
The price is NZ$861
includes taxes & fees
30 May - 31 May
Luxury Home Near West Point

Room for Everyone: Spacious 6BR West Point Retreat

Room for Everyone: Spacious 6BR West Point Retreat
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Great location for Westpoint visit. As described. Clean with new updates. "
United States
Alain C.
The price is NZ$1,893
includes taxes & fees
4 June - 5 June
Room for Everyone: Spacious 6BR West Point Retreat

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (2 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is NZ$527
includes taxes & fees
20 May - 21 May
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is NZ$173
includes taxes & fees
14 June - 15 June
1 King Bed | Non-Smoking, Kitchen, Shower

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (16 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$262
includes taxes & fees
20 May - 21 May
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Highlands Hotel Reviews

Find out more about Town of Highlands

Everything you need to know about Town of Highlands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Highlands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Highlands holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Highlands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Highlands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Highlands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Highlands holiday rentals we have selected for you start as low as NZ$548 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Highlands rentals

At Expedia, we put the best Town of Highlands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Highlands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Highlands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Highlands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.