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

Highland Mills Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Highland Mills vacation rentals

A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

1. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very Good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
$697 nightly
The price is $823
Aug 30 - Aug 31
Total with taxes and fees
Perfect and Spacious Hudson Valley Escape!

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Visiting West Point for ring weekend. Location was great and the reason we chose the place. Property itself could really use some TLC, but it met our needs. Communication with the owner was good and gaining access to the property was straightforward. Would consider staying here again just based on the close proximity to West Point."
United States
Kevin
$229 nightly
The price is $254
Sep 2 - Sep 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A wooden coffee table with two decorative planters in a living room.

3. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (25 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$247 nightly
The price is $272
Aug 31 - Sep 1
Total with taxes and fees
Walk to WP Gate + Free Parking!
A spacious living room with a fireplace, a ceiling fan, and a large window.

4. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (8 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
$433 nightly
The price is $490
Aug 30 - Aug 31
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A house with a view of a bridge and mountains.

5. 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, (141 reviews)
"We had a great stay!!"
United States
Jasmine
$284 nightly
The price is $335
Sep 1 - Sep 2
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A deck with Adirondack chairs, a fire pit, and a grill.

6. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (13 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$343 nightly
The price is $405
Sep 1 - Sep 2
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

7. 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.
$191 nightly
The price is $216
Sep 9 - Sep 10
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
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, (21 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$141 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A living room with a fireplace, a painting, shelves with decorative items, and a television.

9. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 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.
$257 nightly
The price is $291
Aug 31 - Sep 1
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

10. 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, (46 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
$219 nightly
The price is $248
Sep 21 - Sep 22
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A spacious living room with a fireplace, a ceiling fan, and a large window.

11. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
$457 nightly
The price is $517
Aug 30 - Aug 31
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

12. Cottage Suites

Cottage Suites
3.0 star property
Middletown
5.4 out of 10, (10 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
$151 nightly
The price is $171
Sep 3 - Sep 4
Total with taxes and fees
Cottage Suites
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

13. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$284 nightly
The price is $296
Sep 4 - Sep 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A wooden cabin with large windows, a wooden bench, and a view of the forest.

14. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Aug 31 - Sep 1
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
A foyer with a chandelier, a welcome mat, and a small table with magazines.

15. Entire 1 Bedroom Apartment in Lovely Family Vacation Lake House. Pets welcome!

Entire 1 Bedroom Apartment in Lovely Family Vacation Lake House. Pets welcome!
Greenwood Lake
10.0 out of 10, Exceptional, (14 reviews)
"Everything was perfect. Wonderful stay"
United States
Beth M.
$399 nightly
The price is $451
Sep 4 - Sep 5
Total with taxes and fees
Entire 1 Bedroom Apartment in Lovely Family Vacation Lake House. Pets welcome!
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (19 reviews)
"Great place to stay,"
United States
Anonymous traveler
$82 nightly
The price is $94
Sep 1 - Sep 2
Total with taxes and fees
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

17. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$74 nightly
The price is $83
Sep 16 - Sep 17
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

18. 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.
$360 nightly
The price is $402
Sep 1 - Sep 2
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$436 nightly
The price is $481
Aug 31 - Sep 1
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

20. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
10.0 out of 10, Exceptional, (16 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
$617 nightly
The price is $729
Aug 31 - Sep 1
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

8/10 Good
"Professional & helpful staff Breakfast selection was very good"
John 3-night trip
Posted less than an hour ago
Sleep Inn & Suites Monroe - Woodbury

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 $94 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?

Perfect and Spacious Hudson Valley Escape!: Visitors give good reviews to this Highland Mills vacation home rental, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.