Highland Mills Vacation Rentals from CA $125: Short-Term Rentals for 2026

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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!

Highland Falls

Andrew L.

CA $439 total

includes taxes & fees

Nov 10 - Nov 11

A house with a view of a bridge and mountains.

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

CA $429 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a porch, a table, and chairs outside.

3. Historic Horse Barn Apartment in Goshen

Goshen

CA $276 total

includes taxes & fees

Nov 12 - Nov 13

A deck with Adirondack chairs, a fire pit, and a grill.

4. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

CA $619 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living room with a fireplace, a ceiling fan, and a large window.

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

Scott

CA $762 total

includes taxes & fees

Nov 30 - Dec 1

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

Highland Falls

Zack C.

CA $272 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Highland Falls

Maria L.

CA $352 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Highland Falls

Morgan S.

CA $588 total

includes taxes & fees

Nov 10 - Nov 11

A blue house with a white porch, a welcome sign, and a mailbox.

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

Highland Falls

Christine T.

CA $633 total

includes taxes & fees

Nov 10 - Nov 11

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

10. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

CA $413 total

includes taxes & fees

Nov 10 - Nov 11

A hallway with a wooden door, a black table with a sign, and large green plants.

11. 3BR Near West Point | Coffee Bar | Sleeps 6

Highland Falls

mario b.

CA $573 total

includes taxes & fees

Nov 10 - Nov 11

A wooden coffee table with two decorative planters in a living room.

12. Walk to WP Gate + Free Parking!

Highland Falls

Jerell T.

CA $383 total

includes taxes & fees

Nov 10 - Nov 11

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

Goshen

Jessica C.

CA $399 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Highland Falls

CA $443 total

includes taxes & fees

Nov 10 - Nov 11

A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

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

Warwick

Joseph

CA $218 total

includes taxes & fees

Nov 10 - Nov 11

A room with a wooden floor, a white door with a number, and a window with blinds.

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

Highland Falls

Briana T.

CA $424 total

includes taxes & fees

Nov 10 - Nov 11

A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

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

Warwick

Natalie M.

CA $339 total

includes taxes & fees

Nov 15 - Nov 16

A modern bedroom with a blue sofa, a bed, a TV, and a window with a view.

18. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Beacon

Maryanne

CA $345 total

includes taxes & fees

Nov 24 - Nov 25

A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

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

Greenwood Lake

Tara

CA $382 total

includes taxes & fees

Nov 10 - Nov 11

A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

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

Monroe

Kimberly R.

CA $996 total

includes taxes & fees

Nov 10 - Nov 11

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Find vacation rentals that suit your style

Top Highland Mills Hotel Reviews

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Helene

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

Alex

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

Blair

A large, two-story white house with a wrap-around porch and a small front garden.

The Dominion House Bed & Breakfast

Chester

10/10 Excellent

I’m torn between telling everyone about Dominion House and keeping it to myself. What a glorious B&B, with a swimming pool too. Only 3 rooms so you never feel crowded. Kathy was a welcome host and Liane’s breakfasts were amazing. It was really hot over the weekend, but the house was cool so even though it has A/C, I was still able to sleep with the windows open. So quiet and still. A family of deer wandered the lawn. The bed was comfortable, the water pressure was great, the library had tons of...

Susan

A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

10/10 Excellent

Bahaiddine

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Anonymous traveller

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

10/10 Excellent

Sumaya

A hotel with a parking lot, a swimming pool, and a view of a lake and mountains.

West Point Motel

Highland Falls

10/10 Excellent

Anonymous traveller

A buffet with various food items, including omelets and baked goods, served in metal trays.

Holiday Inn Express & Suites Montgomery by IHG

Montgomery

10/10 Excellent

Joey

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

Candlewood Suites Middletown Goshen by IHG

Middletown

8/10 Good

Stamatia

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 $125 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.

Highland Mills Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Highland Mills vacation rentals

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

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

3. Historic Horse Barn Apartment in Goshen

4. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

5. Hudson Valley Retreat w/ Pool Near Greenwood Lake

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

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

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

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

10. Fabulous 3bdrm Home w/parking!

11. 3BR Near West Point | Coffee Bar | Sleeps 6

12. Walk to WP Gate + Free Parking!

13. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

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

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

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

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

18. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

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

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

Find vacation rentals that suit your style

Top Highland Mills Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

Find out more about Highland Mills

Highland Mills vacation rentals: An excellent choice for every season

How to find incredible deals on Highland Mills rentals

Frequently Asked Questions

Can I find a vacation rental in Highland Mills?

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

How many vacation rentals will I find in Highland Mills?

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

What’s a vacation rental in Highland Mills like?