A suspension bridge over a river with a sunset in the background.

Town of Highlands Holiday Rentals

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Our top choices for Town of Highlands holiday rentals

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AU$404
includes taxes & fees
17 Nov - 18 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

2. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 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 AU$297
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom retreat minutes from West Point!

3. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is AU$603
includes taxes & fees
15 Nov - 16 Nov
Local Artist Inspired | Walk to WestPoint + King Bed

4. 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, (7 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 AU$444
includes taxes & fees
17 Nov - 18 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

5. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is AU$484
includes taxes & fees
14 Dec - 15 Dec
Perfect 2BR with Free Parking! Walk to West Point!

6. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is AU$481
includes taxes & fees
8 Dec - 9 Dec
Walk to WP Gate + Free Parking!

7. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is AU$591
includes taxes & fees
15 Nov - 16 Nov
3BR Near West Point | Coffee Bar | Sleeps 6

8. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AU$458
includes taxes & fees
17 Nov - 18 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 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.
3BR West Point Retreat-3min to Back Gate+ King Bed

10. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is AU$523
includes taxes & fees
8 Dec - 9 Dec
Fabulous 3bdrm Home w/parking!

11. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is AU$451
includes taxes & fees
15 Nov - 16 Nov
Mountain-View 2BR Steps from Thayer Gate

12. 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 AU$514
includes taxes & fees
8 Dec - 9 Dec
Lovely 3BR Home with parking-Walk to WP Gate!

13. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is AU$687
includes taxes & fees
8 Dec - 9 Dec
Hudson Valley/West Point Retreat w/ parking!

14. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is AU$132
includes taxes & fees
28 Nov - 29 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

15. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (20 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is AU$117
includes taxes & fees
8 Dec - 9 Dec
1 King Bed | Non-Smoking, Kitchen, Shower

16. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (41 reviews)
"Great location very walkable"
United States
Tim B.
The price is AU$351
includes taxes & fees
16 Nov - 17 Nov
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

17. Private River View Deck ยท Walk Downtown

Private River View Deck ยท Walk Downtown
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is AU$584
includes taxes & fees
17 Nov - 18 Nov
Private River View Deck ยท Walk Downtown

18. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
3.5 star property
Goshen
The price is AU$282
includes taxes & fees
14 Nov - 15 Nov
Historic Horse Barn Apartment in Goshen

19. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
The price is AU$755
includes taxes & fees
15 Nov - 16 Nov
Walk-to-Lake Cottage With Grill for Peaceful Fall Days

20. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (59 reviews)
"Great location, comfortable spot to sleep in after being out all day."
United States
Kelena B.
The price is AU$422
includes taxes & fees
1 Dec - 2 Dec
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
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 youโ€™re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, weโ€™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 onโ€ฆ and on!

Thereโ€™s just as wide a choice of amenities, too. Maybe youโ€™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 favourite filters to narrow down your search.ย 

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 youโ€™re looking for a little peace, consider booking during the quieter months, such as ย . For more hustle and bustle, you may prefer to visit in .ย 

Prices vary throughout the year and depend 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 groupsย andย 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.โ€ฏThe selection of Town of Highlands holiday rentals we have chosen for you start as low as AU$132 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. Youโ€™ll always find a great deal with Expedia.ย 

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 wantโ€”and just like that, youโ€™ve built your dream Town of Highlands holiday.

If youโ€™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.ย