Highland Mills Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Highland Mills vacation rentals

A historic building with a central tower labeled 'West Point Museum,' featuring a traditional architectural style with multiple windows and a stone facade.

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 CA $170
CA $423 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Living area

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 CA $156
CA $282 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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 CA $176
CA $585 total
includes taxes & fees
Nov 9 - Nov 10
Local Artist Inspired | Walk to WestPoint + King Bed
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
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
The price is CA $300
CA $762 total
includes taxes & fees
Nov 30 - Dec 1
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A two-story house with a porch, a table, and chairs outside.

5. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is CA $253
CA $312 total
includes taxes & fees
Nov 12 - Nov 13
Historic Horse Barn Apartment in Goshen
Interior

6. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (54 reviews)
"Great location in the heart of Warwick, NY. Easy to walk around town and visit the local restaurants!"
United States
Francis
The price is CA $148
CA $315 total
includes taxes & fees
Nov 30 - Dec 1
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

7. 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 CA $215
CA $379 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A deck with Adirondack chairs, a fire pit, and a grill.

8. 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, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is CA $321
CA $619 total
includes taxes & fees
Nov 9 - Nov 10
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A blue house with a white porch, a welcome sign, and a mailbox.

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.
The price is CA $186
CA $650 total
includes taxes & fees
Nov 11 - Nov 12
3BR West Point Retreat-3min to Back Gate+ King Bed
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

10. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (22 reviews)
"Great place, but you can hear red everything going on outside your room with the restaurant downstairs and other people in the common area. But I’d definitely come back here"
United States
Joseph
The price is CA $127
CA $208 total
includes taxes & fees
Nov 9 - Nov 10
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

11. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is CA $78
CA $192 total
includes taxes & fees
Nov 9 - Nov 10
Columbus Suites
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

12. 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.
The price is CA $173
CA $331 total
includes taxes & fees
Nov 17 - Nov 18
Historic Cabin with Pool & Fire Pit
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

13. 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 CA $242
CA $445 total
includes taxes & fees
Nov 9 - Nov 10
Fabulous 3bdrm Home w/parking!
A modern kitchen with wooden cabinets, a stainless steel stove, a microwave, and a toaster. There are stools and a small island with a plant.

14. 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 CA $242
CA $413 total
includes taxes & fees
Nov 9 - Nov 10
Walk to WP Gate + Free Parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

15. 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 CA $242
CA $457 total
includes taxes & fees
Nov 9 - Nov 10
Lovely 3BR Home with parking-Walk to WP Gate!
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

16. 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.
The price is CA $210
CA $399 total
includes taxes & fees
Nov 12 - Nov 13
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A stone pathway leading to a stone wall with a potted plant.

17. Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is CA $283
CA $435 total
includes taxes & fees
Nov 9 - Nov 10
Villa Verde B&B, Greenwood Lake NY, 1
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

18. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
The price is CA $311
CA $382 total
includes taxes & fees
Nov 9 - Nov 10
Villa Verde B&B, bsm, Greenwood Lake NY
A living room with a fireplace, a painting, shelves with decorative items, and a television.

19. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is CA $280
CA $508 total
includes taxes & fees
Nov 9 - Nov 10
Grant - A Tranquil One Bedroom Steps from River
A brick building with a sign reading 'Lobby' in front.

20. 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 CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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

A hotel entrance with stone pillars, a covered walkway, and a bench.
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe

10/10 Excellent

Excellent rapport qualité prix. Le meilleur ds le coin. Rien à redire.
Canada
Helene
Reviewed July 25, 2024
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, 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 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 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 Highland Mills vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Mills vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard 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.

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.