A calm lake at sunset with trees and grass along the shore.

Highland Mills Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Highland Mills vacation rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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.
$302 nightly
The price is $311
Oct 18 - Oct 19
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$404 nightly
The price is $434
Oct 21 - Oct 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a view of a bridge and mountains.

3. 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, (148 reviews)
"We had a great stay!!"
United States
Jasmine
$279 nightly
The price is $330
Oct 20 - Oct 21
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Living area

4. 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.
$186 nightly
The price is $205
Oct 18 - Oct 19
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

5. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (47 reviews)
"Always a pleasure staying here."
United States
Natalie M.
$214 nightly
The price is $242
Oct 21 - Oct 22
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

6. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Carriage House Apartment Goshen NY
A living room with a fireplace, a painting, shelves with decorative items, and a television.

7. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$262 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A room with a chandelier, a sofa, a table, and a cabinet.

8. 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
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$146 nightly
The price is $165
Oct 27 - Oct 28
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A deck with Adirondack chairs, a fire pit, and a grill.

9. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$369 nightly
The price is $436
Oct 21 - Oct 22
Total with taxes and fees
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A two-story house with a porch, a table, and chairs outside.

10. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
Historic Horse Barn Apartment in Goshen
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

11. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$299 nightly
The price is $312
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

12. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"It was a great place "
United States
Jose
$173 nightly
The price is $196
Oct 18 - Oct 19
Total with taxes and fees
Columbus Suites
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
$459 nightly
The price is $471
Nov 2 - Nov 3
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

14. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$207 nightly
The price is $245
Oct 19 - Oct 20
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

15. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (3 reviews)
"This location was perfect for our yearly fall gathering. It is 15 minutes from Pure Terror Scream Park and nestled in a historic town. The unit was clean, spacious, and perfect for a group of 7-8 people. The hosts were very helpful and prompt with instructions. I would recommend this stay if you are looking to stay in Goshen, NY."
United States
Tammy
Hay Loft Apartment in Barn - Goshen
A blue house with a white porch, a welcome sign, and a mailbox.

16. 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
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$441 nightly
The price is $453
Nov 2 - Nov 3
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

18. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
$437 nightly
The price is $449
Oct 21 - Oct 22
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A wooden cabin with large windows, a wooden bench, and a view of the forest.

19. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
Harriman Outdoor Center - Mountain Laurel Cabin
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

20. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$79 nightly
The price is $89
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
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 Highland Mills Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Had a pleasant stay. Lovely relaxing indoor area with restaurant & bar. Clean room & staff were very attentive & helpful."
Sharon 1-night trip
Posted 4 hours ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Highland Mills

Everything you need to know about Highland Mills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Mills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Highland Mills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Mills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Mills. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Mills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Mills rentals

At Expedia, we put the best Highland Mills vacation 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 Highland Mills 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 Highland Mills vacation.

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

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Highland Mills?

Yes, there are vacation rentals close to the most popular attractions in Highland Mills, or you can select a more remote option if you want a relaxing place to stay. Highland Mills is known for its shopping and wineries. Make sure you have time to check out the forests and temples during your trip.

What are some of the best vacation home rentals that Highland Mills has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Highland Mills is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Highland Mills?

Choose from 7 Expedia vacation rentals in Highland Mills for a memorable vacation.

What’s there to see and do in Highland Mills?

While exploring the area, visit family-friendly sights like Castle Fun Center, or get outside and enjoy nature at Arrow Park Lake and Lodge. While here, United States Military Academy and Palaia Vineyards Winery are other places worth a visit.

What’s a vacation rental in Highland Mills like?

A vacation rental is a private property you can book for a long or short time in Highland Mills. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.