Highland Mills Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Highland Mills holiday rentals

10.0 out of 10, Exceptional, (1 review)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is NZ$1,225
includes taxes & fees
27 Feb - 28 Feb
Perfect and Spacious Hudson Valley Escape!
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$314
includes taxes & fees
11 Mar - 12 Mar
Cozy 1-bedroom retreat minutes from West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is NZ$453
includes taxes & fees
4 Mar - 5 Mar
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is NZ$486
includes taxes & fees
27 Feb - 28 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is NZ$333
includes taxes & fees
1 Mar - 2 Mar
Cabin in the heart of the Hudson Valley, Cabin 4
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is NZ$399
includes taxes & fees
3 Mar - 4 Mar
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is NZ$505
includes taxes & fees
27 Feb - 28 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.0 out of 10, Wonderful, (8 reviews)
"The bed was very comfortable! Loved the sitting area in the room! The downstairs of this location is an excellent restaurant! "
United States
Annette L.
The price is NZ$253
includes taxes & fees
3 Mar - 4 Mar
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
2.0 star property
The price is NZ$575
includes taxes & fees
1 Mar - 2 Mar
Calm Boutique Lake Studio Fast Wifi Great WFH
10.0 out of 10, Exceptional, (74 reviews)
"Wonderful, clean accommodations, with very responsive host."
United States
Connor H.
The price is NZ$363
includes taxes & fees
2 Mar - 3 Mar
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is NZ$463
includes taxes & fees
1 Mar - 2 Mar
Cabin in the Heart of the Hudson Valley, Cabin 1
10.0 out of 10, Exceptional, (35 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is NZ$424
includes taxes & fees
2 Mar - 3 Mar
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
9.4 out of 10, Exceptional, (60 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is NZ$464
includes taxes & fees
1 Mar - 2 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
The price is NZ$417
includes taxes & fees
1 Mar - 2 Mar
Rustic Lakefront Studio with Deck & Workspace
8.0 out of 10, Very good, (6 reviews)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is NZ$730
includes taxes & fees
4 Mar - 5 Mar
3BR West Point Retreat-3min to Back Gate+ King Bed
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$588
includes taxes & fees
2 Mar - 3 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
9.0 out of 10, Wonderful, (10 reviews)
"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.
The price is NZ$428
includes taxes & fees
1 Mar - 2 Mar
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.8 out of 10, Exceptional, (90 reviews)
"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.
The price is NZ$518
includes taxes & fees
1 Mar - 2 Mar
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
The price is NZ$434
includes taxes & fees
1 Mar - 2 Mar
Stylish & Pet-Friendly Apartment in Beacon
9.8 out of 10, Exceptional, (67 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
The price is NZ$522
includes taxes & fees
27 Feb - 28 Feb
Cozy country efficiency in the Hudson Valley
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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 holiday rentals

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

Highland Mills holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Mills holiday rentals we have selected for you start as low as NZ$333 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 holiday 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 holiday.

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 holiday rental in Highland Mills?

Yes, there are holiday rentals close to the most popular sights in Highland Mills, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Highland Mills has to offer?

Perfect and Spacious Hudson Valley Escape!: This highly rated holiday home rental in Highland Mills has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Highland Mills?

Choose from 3 Expedia holiday rentals in Highland Mills for a memorable holiday.

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 holiday rental in Highland Mills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland Mills. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.