Highland Mills Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

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 ￥55,949
￥131,597 total
includes taxes & fees
Apr 5 - Apr 6
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 ￥29,645
￥68,413 total
includes taxes & fees
Apr 13 - Apr 14
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, (3 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 ￥16,224
￥32,819 total
includes taxes & fees
Apr 12 - Apr 13
Historic Cabin with Pool & Fire Pit
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, (7 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥20,359
￥62,349 total
includes taxes & fees
Apr 1 - Apr 2
House on the Babbling Brook- Quiet 2BR + King Bed!
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, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥13,937
￥29,030 total
includes taxes & fees
Apr 20 - Apr 21
Cozy 1-bedroom retreat minutes from West Point!
Fridge, oven, stovetop, coffee/tea maker

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, (18 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥18,378
￥48,315 total
includes taxes & fees
Apr 5 - Apr 6
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥30,044
￥48,270 total
includes taxes & fees
Apr 5 - Apr 6
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
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 ￥26,711
￥78,122 total
includes taxes & fees
Apr 8 - Apr 9
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is ￥20,615
￥31,904 total
includes taxes & fees
Apr 7 - Apr 8
Cabin in the heart of the Hudson Valley, Cabin 4
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 ￥23,732
￥46,916 total
includes taxes & fees
Apr 1 - Apr 2
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (49 reviews)
"Great place!"
United States
Sara B.
The price is ￥18,378
￥39,924 total
includes taxes & fees
Apr 7 - Apr 8
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
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
8.8 out of 10, Excellent, (9 reviews)
"The bed was very comfortable! Loved the sitting area in the room! The downstairs of this location is an excellent restaurant! "
United States
Annette L.
The price is ￥13,520
￥23,972 total
includes taxes & fees
Apr 1 - Apr 2
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
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, (78 reviews)
"great location and nice host"
United States
christopher s.
The price is ￥22,387
￥42,671 total
includes taxes & fees
Apr 2 - Apr 3
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Exterior

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 reviews)
"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 ￥24,307
￥41,239 total
includes taxes & fees
Apr 3 - Apr 4
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Desk, free WiFi, bed sheets

'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 reviews)
"Great stay!"
United States
Ann S.
The price is ￥33,566
￥59,775 total
includes taxes & fees
May 1 - May 2
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
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, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is ￥27,008
￥44,741 total
includes taxes & fees
Apr 1 - Apr 2
Cabin in the Heart of the Hudson Valley, Cabin 1
3 bedrooms, desk, iron/ironing board, free WiFi

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"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 ￥20,039
￥69,442 total
includes taxes & fees
Apr 1 - Apr 2
Sleek Escape: Modern 3 BR- 4 Min from West Point !
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ￥31,962
￥50,609 total
includes taxes & fees
Apr 20 - Apr 21
Luxury House Near West Point
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is ￥19,976
￥72,136 total
includes taxes & fees
Apr 1 - Apr 2
3BR West Point Retreat-3min to Back Gate+ King Bed
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, (38 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is ￥18,275
￥41,712 total
includes taxes & fees
Apr 1 - Apr 2
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"This Hotel and specialty their staff exceeded my expectations. All areas were clean and functional, is not common to find a gym where all the equipment works. Quality of Breakfast and cleanliness was excellent. Room spacey and comfy. Definitely will be a regular as I love hiking in that area."
Pedro 1-night trip
Posted 7 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

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:

  • View our selection of featured holiday rentals in Highland Mills
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  • Enter your travel dates to view the best deals on holiday rentals in Highland Mills while they last

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?

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 4 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 The Rock Sports Complex. 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.