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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Highland Mills vacation rentals

Private kitchen

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.
The price is ￥55,802
￥131,251 total
includes taxes & fees
Aug 17 - Aug 18
Perfect and Spacious Hudson Valley Escape!
Property grounds

2. 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
The price is ￥31,559
￥53,096 total
includes taxes & fees
Aug 17 - Aug 18
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cottage (2 Bedrooms) | Interior

3. 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, (3 reviews)
"fantastic accommodations"
United States
David
The price is ￥33,791
￥82,341 total
includes taxes & fees
Aug 30 - Aug 31
Hudson Valley Retreat w/ Pool Near Greenwood Lake
TV

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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 ￥23,430
￥41,790 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 1-bedroom retreat minutes from West Point!
Outdoor spa tub

5. 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, (11 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥37,775
￥73,617 total
includes taxes & fees
Sep 2 - Sep 3
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Interior

6. 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
9.0 out of 10, Wonderful, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is ￥14,919
￥25,533 total
includes taxes & fees
Aug 17 - Aug 18
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Smart TV

7. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is ￥23,669
￥47,270 total
includes taxes & fees
Aug 19 - Aug 20
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Smart TV

8. 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)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is ￥21,518
￥45,980 total
includes taxes & fees
Aug 24 - Aug 25
Grant - A Tranquil One Bedroom Steps from River
1 bedroom, WiFi (free), bed sheets

9. 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, (45 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.
The price is ￥20,083
￥44,357 total
includes taxes & fees
Aug 20 - Aug 21
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Exterior

10. 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 ￥18,591
￥36,357 total
includes taxes & fees
Sep 1 - Sep 2
Historic Cabin with Pool & Fire Pit
Coffee/tea maker, fridge, microwave, oven

11. 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 ￥41,170
￥66,494 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
1 bedroom, WiFi (free)

12. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥12,957
￥14,657 total
includes taxes & fees
Sep 1 - Sep 2
2 Queen Beds | Non-Smoking, Kitchen
Interior

13. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥31,240
￥36,211 total
includes taxes & fees
Aug 30 - Aug 31
Harriman Outdoor Center - Mountain Laurel Cabin
Property grounds

14. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (92 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is ￥15,716
￥34,381 total
includes taxes & fees
Aug 16 - Aug 17
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

15. 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 ￥39,848
￥51,389 total
includes taxes & fees
Aug 16 - Aug 17
Villa Verde B&B, bsm, Greenwood Lake NY
Coffee/tea maker, fridge, microwave, oven

16. 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)
"The host was welcoming and easy to reach. It’s a lovely, fully stocked house that had everything we needed. Check-in and check-out were a breeze. Nice, quiet location."
United States
Michael M.
The price is ￥55,787
￥118,429 total
includes taxes & fees
Aug 19 - Aug 20
Amazing Home Near West Point, Shopping, Skiing and Legoland
Outdoor dining

17. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is ￥20,561
￥32,196 total
includes taxes & fees
Aug 16 - Aug 17
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior

18. 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
The price is ￥11,660
￥13,481 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Coffee/tea maker, fridge, microwave, oven

19. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥35,863
￥67,818 total
includes taxes & fees
Aug 17 - Aug 18
Contemporary Cozy Cottage
Exterior detail

20. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥32,979
￥86,848 total
includes taxes & fees
Aug 17 - Aug 18
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"We were able to check-in late and the room was clean and comfortable."
Alma 1-night trip
Posted 3 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG

Find out more about Highland Mills

Search for holiday rentals in Highland Mills on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Mills using one of the methods below:

  • View our selection of featured holiday rentals in Highland Mills
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  • Enter your travel dates to view the best deals on holiday rentals in Highland Mills while they last

Look no further and take a look at our great range of rental properties in Highland Mills!

Frequently asked questions

Can I find a vacation rental in Highland Mills?

Yes, there are vacation rentals where you'll be just 9.8 mi (15.8 km) from LEGOLAND® New York, giving you a more remote option if you want a quieter 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 LEGOLAND® New York, 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.