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

Search Holiday Homes in Highland Mills

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Highland Mills holiday homes

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 £610
includes taxes & fees
17 Jul - 18 Jul
Perfect and Spacious Hudson Valley Escape!
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 £151
includes taxes & fees
19 Jul - 20 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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 £306
includes taxes & fees
21 Jul - 22 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!
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, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is £145
includes taxes & fees
22 Jul - 23 Jul
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is £386
includes taxes & fees
29 Jul - 30 Jul
Fabulous 3bdrm Home w/parking!
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, (70 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is £252
includes taxes & fees
29 Jul - 30 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, oven, stovetop

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 £316
includes taxes & fees
27 Jul - 28 Jul
Contemporary Cozy Cottage
Coffee/tea maker, fridge, microwave, oven

3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"My wife and I traveled to West Point this weekend with my brother-in-law and sister-in-law to see our son compete in Army Navy track meet. I the house was perfect for us and an easy drive to West Point. House was clean, and well organized. We would stay again."
United States
Ronnie S.
The price is £411
includes taxes & fees
20 Jul - 21 Jul
3BR Hudson Valley home perfect for families!
Property grounds

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (59 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is £304
includes taxes & fees
20 Jul - 21 Jul
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Outdoor spa tub

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, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is £344
includes taxes & fees
20 Jul - 21 Jul
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Coffee/tea maker, fridge, microwave, oven

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, (14 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 £376
includes taxes & fees
24 Jul - 25 Jul
Amazing Home Near West Point, Shopping, Skiing and Legoland
Fridge, oven, stovetop, dishwasher

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and really cute place. "
United States
Katie C.
The price is £445
includes taxes & fees
19 Jul - 20 Jul
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat
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 £397
includes taxes & fees
29 Jul - 30 Jul
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (14 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is £127
includes taxes & fees
27 Jul - 28 Jul
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds

Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains

Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
wallkill
9.6 out of 10, Exceptional, (5 reviews)
"Everything was very nice, clean, easy access to things and great location!Loved the area! Host was wonderful!!I’d stay there again!!"
United States
Dauna A.
The price is £422
includes taxes & fees
27 Jul - 28 Jul
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (39 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is £468
includes taxes & fees
19 Jul - 20 Jul
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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 £524
includes taxes & fees
20 Jul - 21 Jul
Chestnut on Willow Lake
Smart TV, offices

River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington
Newburgh
The price is £651
includes taxes & fees
17 Jul - 18 Jul
River Views & Hot Tub | Riverview on Washington
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 £928
includes taxes & fees
28 Jul - 29 Jul
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is £550
includes taxes & fees
20 Jul - 21 Jul
Red Cottage - Lakeside Property!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Mills Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"The staff at the front desk, Michael and Sara were very polite, helpful and professional. The cleaning staff was helpful and so was the breakfast staff. The bed was super comfortable and the rooms were clean. The only thing I wish our room had was a microwave…besides that everything was great. I’ll definitely stay at this HP again!!!"
Nada 2-night trip
Posted 16 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Highland Mills

Highland Mills Holiday Homes information

Number of reviews
312
Accommodation
274 Holiday Homes
Lowest Price
£127
Highest Price
£928