Highland Mills Vacation Rentals

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Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Highland Mills vacation rentals

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥14,796
￥29,695 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is ￥14,091
￥41,650 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is ￥17,019
￥57,547 total
includes taxes & fees
Jan 12 - Jan 13, 2026
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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is ￥13,809
￥24,125 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

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, (90)
"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 ￥17,547
￥43,109 total
includes taxes & fees
Dec 28 - Dec 29
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is ￥16,863
￥40,450 total
includes taxes & fees
Dec 30 - Dec 31
Grant - A Tranquil One Bedroom Steps from River
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is ￥23,187
￥45,682 total
includes taxes & fees
Dec 29 - Dec 30
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is ￥20,298
￥68,769 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is ￥24,514
￥45,218 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Villa Verde B&B, bsm, Greenwood Lake NY
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,388
￥43,527 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cabin in the heart of the Hudson Valley, Cabin 3
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is ￥16,231
￥37,852 total
includes taxes & fees
Jan 5 - Jan 6, 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is ￥17,175
￥37,568 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is ￥23,749
￥40,292 total
includes taxes & fees
Dec 28 - Dec 29
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Fridge, microwave, oven, stovetop
Cozy Modern Stay - Walk to West Point & Main St!

Cozy Modern Stay - Walk to West Point & Main St!

Cozy Modern Stay - Walk to West Point & Main St!
2.0 star property
Highland Falls
The price is ￥10,960
￥56,480 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Modern Stay - Walk to West Point & Main St!
Fridge, microwave, oven, stovetop
Cabin in the Heart of the Hudson Valley, Cabin 1

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, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is ￥26,388
￥43,527 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cabin in the Heart of the Hudson Valley, Cabin 1
Dining
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

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, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is ￥18,737
￥40,628 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Lux APT Your home away from home.

Lux APT Your home away from home.
Beacon
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is ￥22,172
￥42,216 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Lux APT Your home away from home.
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ￥17,175
￥62,570 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Local Artist Inspired | Walk to WestPoint + 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!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is ￥18,037
￥36,335 total
includes taxes & fees
Dec 29 - Dec 30
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is ￥25,576
￥43,799 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free 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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"Very well service "
Jennifer 1-night trip
Posted 2 days ago
Hampton Inn by Hilton Middletown

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 vacation rental in Highland Mills?

Yes, there are vacation rentals close to the most popular attractions in Highland Mills, or you can select a more remote option if you want a relaxing 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Highland Mills offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Highland Mills?

Choose from 3 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 Castle Fun Center, or get outside and enjoy nature at Storm King Art Center. 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.