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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 253 Vacation Homes in Highland Mills with updated reviews, rates, and availability.

Greenwoods of Warwick
Exterior

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick
Majestic RiverView Estate - Breathtaking Views
View of the house (Pool not included)

Majestic RiverView Estate - Breathtaking Views

10.0 out of 10, Exceptional, (4)
"We booked a weekend away to celebrate family birthdays and were very happy to celebrate in such a special place. There was plenty of room for 11 of us (+ dog) and was a mix of modern touches and old world charm highlighting the legacy of the house. And the view of the Hudson was a highlight of our stay. Highly recommend!"
Majestic RiverView Estate - Breathtaking Views
Cozy Indoor Hot Tub, Fire Pit & Game Room

Cozy Indoor Hot Tub, Fire Pit & Game Room

9.6 out of 10, Exceptional, (4)
"It was a wonderdul and relaxing stay with the family"
Cozy Indoor Hot Tub, Fire Pit & Game Room
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AED 951
AED 1,073 total
includes taxes & fees
23 Jan - 24 Jan
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Private kitchen

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson Vacation Rental | 3BR | 2BA | Stairs Required to Access

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (11)
"Excellent location in Cornwall-on-Hudson. Walking distance to coffee shop and restaurants. Happy to see Painter's Tavern has reopened. 2 Alices-a nice coffee shop to hang out. Home is bright and spacious with contemporary decor. Fully stocked. Two bathrooms a bonus for five of us. Planning to return next holiday season."
Bright Cornwall-On-Hudson Vacation Rental!
Updated Home w/ Patio Half Mile to West Point
Highland Falls Vacation Rental | 3BR | 2BA | 1,100 Sq Ft | 2 Stories

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (23)
"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "
Updated Home w/ Patio Half Mile to West Point
Up-to-date Home w/ Pool, Playground & Fireplace!

Up-to-date Home w/ Pool, Playground & Fireplace!

10.0 out of 10, Exceptional, (1)
Up-to-date Home w/ Pool, Playground & Fireplace!
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Private kitchen

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (1)
"Alexis was a great host and she was super communicative and easy to reach. The house was clean and prefect size for my group of 6. Most things were stocked but I’d reach out to the host in advance so you can buy anything that isn’t ahead of time. One important thing to note is that the driveway can only fit 2 cars and there isn’t really any street parking. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Very Private Large Home on 22 Acres with Outdoor Kitchen
Living area

Very Private Large Home on 22 Acres with Outdoor Kitchen

Very Private Large Home on 22 Acres with Outdoor Kitchen
Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.
Exterior

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.
Vernon Cozy 2BD Pet-Friendly Mountain Creek
Private kitchen

Vernon Cozy 2BD Pet-Friendly Mountain Creek

The price is AED 514
AED 2,305 total
includes taxes & fees
29 Jan - 30 Jan
Vernon Cozy 2BD Pet-Friendly Mountain Creek
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Exterior

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Elegant and spacious home with sauna and heated pool
Living area

Elegant and spacious home with sauna and heated pool

10.0 out of 10, Exceptional, (1)
"We had a great stay! Cozy vibes and beautiful home. Would love to go back. "
Elegant and spacious home with sauna and heated pool
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Exterior

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.0 out of 10, Good, (14)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Lakefront Luxury on Greenwood Lake
Terrace/patio

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (128)
"We absolutely loved this lake house. We were in town for a wedding and this house was exactly what we needed. Not too far away from a grocery store and restaurants, plenty of space for our family. Large bathroom was great for our family to get ready in. Would love to come back in the summer!"
Lakefront Luxury on Greenwood Lake
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
Lake house directly on Greenwood Lake

Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118

9.8 out of 10, Exceptional, (116)
"Lovely lakefront property.Was absolutely a gem of a spot!However, as we only had 2 pickup trucks to drive during our stay, parking was tight. The listing specifically says “cars”, & I should’ve paid closer attention. And the view out the living room windows more than made up for it!"
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
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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Other property types in Highland Mills

Kick back & relax in this peaceful, stylish place to stay with the whole family.
Aerial view

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (21)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Perfect for families and large groups
Come on in -- the water's fine! Who else is ready to take a dip and soak up some sun?

Perfect for families and large groups

9.6 out of 10, Exceptional, (11)
"Nice house with plenty of room and very clean."
Perfect for families and large groups
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is AED 617
AED 904 total
includes taxes & fees
23 Jan - 24 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.