A calm lake at sunset with trees and grass along the shore.

Highland Mills Holiday Rentals

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Check prices for these dates

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

Our top choices for Highland Mills holiday 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 HK$2,747
HK$6,462 total
includes taxes & fees
17 Aug - 18 Aug
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 HK$1,554
HK$2,614 total
includes taxes & fees
17 Aug - 18 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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 HK$1,664
HK$4,054 total
includes taxes & fees
30 Aug - 31 Aug
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 HK$1,112
HK$2,011 total
includes taxes & fees
15 Sept - 16 Sept
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 HK$1,695
HK$3,402 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$734
HK$1,257 total
includes taxes & fees
17 Aug - 18 Aug
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
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is HK$1,165
HK$2,327 total
includes taxes & fees
26 Aug - 27 Aug
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 HK$1,059
HK$2,317 total
includes taxes & fees
31 Aug - 1 Sept
Grant - A Tranquil One Bedroom Steps from River
1 bedroom, free WiFi, 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 HK$777
HK$1,909 total
includes taxes & fees
24 Aug - 25 Aug
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 HK$907
HK$1,780 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$1,977
HK$3,226 total
includes taxes & fees
15 Sept - 16 Sept
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
1 bedroom, free WiFi

12. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.6 out of 10, Exceptional, (21 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is HK$640
HK$724 total
includes taxes & fees
1 Sept - 2 Sept
2 Queen Beds | Non-Smoking, Kitchen
Interior

13. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is HK$1,538
HK$1,783 total
includes taxes & fees
30 Aug - 31 Aug
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 HK$774
HK$1,693 total
includes taxes & fees
17 Aug - 18 Aug
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 HK$1,962
HK$2,530 total
includes taxes & fees
17 Aug - 18 Aug
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)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
The price is HK$2,746
HK$5,830 total
includes taxes & fees
19 Aug - 20 Aug
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 HK$1,012
HK$1,576 total
includes taxes & fees
23 Aug - 24 Aug
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 traveller
The price is HK$576
HK$666 total
includes taxes & fees
1 Sept - 2 Sept
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, (36 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 HK$1,766
HK$3,339 total
includes taxes & fees
17 Aug - 18 Aug
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, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,632
HK$4,286 total
includes taxes & fees
17 Aug - 18 Aug
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

8/10 Good
"Large rooms, very good breakfast, and easy parking. The fitness center was surprisingly well stocked and had new equipment."
Jessica 1-night trip
Posted 1 hour ago
Hampton Inn Harriman Woodbury

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:

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

Frequently asked questions

Can I find a holiday rental in Highland Mills?

Yes, we give you a choice of holiday rentals where you'll be just 9.8 mi (15.8 km) from LEGOLAND® New York, giving you a secluded option to escape the hustle and bustle. 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 7 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 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 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.