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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Highland Mills vacation rentals

Private kitchen

Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
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 SAR 1,315
SAR 3,092 total
includes taxes & fees
3 Jul - 4 Jul
Perfect and Spacious Hudson Valley Escape!
House | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is SAR 3,750
SAR 5,989 total
includes taxes & fees
1 Jul - 2 Jul
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
9.2 out of 10, Wonderful, (7 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is SAR 3,004
SAR 5,095 total
includes taxes & fees
1 Jul - 2 Jul
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior

1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is SAR 792
SAR 1,008 total
includes taxes & fees
28 Jul - 29 Jul
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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 SAR 394
SAR 743 total
includes taxes & fees
30 Jun - 1 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Smart TV, video games, DVD player, books

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is SAR 987
SAR 1,773 total
includes taxes & fees
22 Jul - 23 Jul
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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)
"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 SAR 829
SAR 1,550 total
includes taxes & fees
21 Jul - 22 Jul
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Interior

Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
United States
Nada S.
The price is SAR 935
SAR 1,175 total
includes taxes & fees
29 Jul - 30 Jul
Polished 1BR w/ Accessible Room Features + Sauna
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is SAR 845
SAR 1,576 total
includes taxes & fees
30 Jun - 1 Jul
Contemporary Cozy Cottage
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is SAR 1,859
SAR 2,599 total
includes taxes & fees
30 Jun - 1 Jul
Chestnut on Willow Lake
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is SAR 1,219
SAR 1,718 total
includes taxes & fees
30 Jun - 1 Jul
Charming Cabin in Fishkill!
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is SAR 1,962
SAR 2,808 total
includes taxes & fees
30 Jun - 1 Jul
Red Cottage - Lakeside Property!
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 SAR 337
SAR 390 total
includes taxes & fees
24 Jul - 25 Jul
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is SAR 337
SAR 382 total
includes taxes & fees
21 Jul - 22 Jul
1 King Bed | Non-Smoking, Kitchen, Shower
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (68 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is SAR 929
SAR 1,214 total
includes taxes & fees
30 Jun - 1 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 SAR 584
SAR 992 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 1-bedroom retreat minutes from West Point!
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is SAR 1,167
SAR 1,810 total
includes taxes & fees
7 Jul - 8 Jul
Walk to WP Gate + Free Parking!
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 SAR 1,011
SAR 1,610 total
includes taxes & fees
30 Jun - 1 Jul
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is SAR 1,068
SAR 1,821 total
includes taxes & fees
1 Jul - 2 Jul
Lovely 3BR Home with parking-Walk to WP Gate!
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is SAR 1,112
SAR 1,826 total
includes taxes & fees
14 Jul - 15 Jul
Fabulous 3bdrm Home w/parking!
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
"Breakfast was very generous!"
Huy 1-night trip
Posted 4 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG

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 Lake Tiorati Beach. 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.