Highland Mills Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

This weekend
Next weekend

Our top choices for Highland Mills vacation rentals

10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$305 nightly
The price is $319
Dec 24 - Dec 25
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$263 nightly
The price is $266
Jan 20 - Jan 21, 2026
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$281 nightly
The price is $293
Dec 24 - Dec 25
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$137 nightly
The price is $155
Jan 5 - Jan 6, 2026
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
$254 nightly
The price is $281
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
9.4 out of 10, Exceptional, (31)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
$169 nightly
The price is $200
Dec 28 - Dec 29
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$366 nightly
The price is $371
Dec 24 - Dec 25
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
$207 nightly
The price is $232
Dec 29 - Dec 30
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
$338 nightly
The price is $382
Dec 25 - Dec 26
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
$216 nightly
The price is $249
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
9.6 out of 10, Exceptional, (41)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
$229 nightly
The price is $259
Dec 29 - Dec 30
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Jan 1 - Jan 2, 2026
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
$228 nightly
The price is $258
Dec 24 - Dec 25
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
$254 nightly
The price is $290
Dec 28 - Dec 29
Total with taxes and fees
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$202 nightly
The price is $233
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
$241 nightly
The price is $273
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lux APT Your home away from home.
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
$230 nightly
The price is $260
Jan 11 - Jan 12, 2026
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$505 nightly
The price is $557
Dec 26 - Dec 27
Total with taxes and fees
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
$396 nightly
The price is $401
Jan 12 - Jan 13, 2026
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
10.0 out of 10, Exceptional, (17)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
$3,093 nightly
The price is $3,236
Dec 30 - Dec 31
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Highland Mills Hotel Reviews

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 $155 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.

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Highland Mills offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Highland Mills?

Choose from 3 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 Storm King Art Center. 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.