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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Highland Mills vacation rentals

Private kitchen

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 AED 1,286
AED 3,025 total
includes taxes & fees
7 Jul - 8 Jul
Perfect and Spacious Hudson Valley Escape!
Property grounds

Lux Cabin on Farm, River, Animals, Projector

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is AED 804
AED 1,710 total
includes taxes & fees
29 Jul - 30 Jul
Lux Cabin on Farm, River, Animals, Projector
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 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 AED 452
AED 861 total
includes taxes & fees
13 Jul - 14 Jul
Historic Cabin with Pool & Fire Pit
Outdoor dining

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 AED 474
AED 742 total
includes taxes & fees
7 Jul - 8 Jul
Cabin in the heart of the Hudson Valley, Cabin 4
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 481
AED 1,458 total
includes taxes & fees
7 Jul - 8 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

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, (85 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is AED 420
AED 866 total
includes taxes & fees
12 Jul - 13 Jul
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is AED 496
AED 1,089 total
includes taxes & fees
13 Jul - 14 Jul
Grant - A Tranquil One Bedroom Steps from River
Property grounds

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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is AED 727
AED 1,215 total
includes taxes & fees
7 Jul - 8 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is AED 621
AED 1,024 total
includes taxes & fees
7 Jul - 8 Jul
Cabin in the Heart of the Hudson Valley, Cabin 1
TV

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 AED 514
AED 910 total
includes taxes & fees
7 Jul - 8 Jul
Cozy 1-bedroom retreat minutes from West Point!
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is AED 386
AED 727 total
includes taxes & fees
7 Jul - 8 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is AED 330
AED 382 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fridge, microwave, oven, stovetop

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 AED 930
AED 1,499 total
includes taxes & fees
7 Jul - 8 Jul
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior detail

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 AED 792
AED 2,004 total
includes taxes & fees
8 Jul - 9 Jul
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Smart TV

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 AED 545
AED 1,075 total
includes taxes & fees
8 Jul - 9 Jul
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Interior

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, (17 reviews)
"Perfect for the weekend event we were attending "
United States
Tara P.
The price is AED 446
AED 704 total
includes taxes & fees
8 Jul - 9 Jul
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (71 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is AED 606
AED 1,154 total
includes taxes & fees
7 Jul - 8 Jul
Cozy country efficiency in the Hudson Valley
1 bedroom, free WiFi, bed sheets, wheelchair access

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, (41 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 AED 446
AED 999 total
includes taxes & fees
7 Jul - 8 Jul
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
1 bedroom, free WiFi

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (19 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is AED 367
AED 415 total
includes taxes & fees
31 Jul - 1 Aug
2 Queen Beds | Non-Smoking, Kitchen
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (92 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is AED 745
AED 1,436 total
includes taxes & fees
21 Jul - 22 Jul
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Everything was good but the bathrooms did not have exhaust gans"
NISHIDH 2-night trip
Posted 4 hours ago
Overlook Lodge at Bear Mountain

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.