Highland Mills Vacation Rentals

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Nov 3 - Nov 4
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Vacation Rentals in Highland Mills

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
9.6 out of 10, Exceptional, (44)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
$292 nightly
The price is $330
Nov 4 - Nov 5
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (124)
"Great place and host!"
United States
Jacqueline
$272 nightly
The price is $308
Nov 9 - Nov 10
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (27)
"This cabin was the perfect size. Clean, private, and made me feel safe and secure. Easily accessible. I would definitely stay here again."
United States
Maryann B.
$149 nightly
The price is $176
Nov 4 - Nov 5
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Nov 4 - Nov 5
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (92)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Smart TV
Grant - A Tranquil One Bedroom Steps from River
Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (37)
"My partner and I came for a gathering of friends and family invthe area. It was the perfect place for us to get away and rest."
United States
Cathy M.
$229 nightly
The price is $259
Nov 4 - Nov 5
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (3)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
United States
Brady K.
$367 nightly
The price is $417
Nov 4 - Nov 5
Total with taxes and fees
Rustic Cabin in Fishkill!
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
10.0 out of 10, Exceptional, (311)
"Beautiful location- owner was very responsive to any questions we had."
United States
Richard K.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Interior
Contemporary Cozy Cottage
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Nov 4 - Nov 5
Total with taxes and fees
Contemporary Cozy Cottage
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy Haven: A Romantic Retreat in our Tiny House!
7.0 out of 10, Good, (9)
"I love the place but the cleanliness was bad, we found a condom under the bed and there was also blood on the bed sheets and a yellow stain on the bed. I’m sorry but for the price I expected something better than this."
United States
Jeferson Eleazar P.
$254 nightly
The price is $300
Nov 4 - Nov 5
Total with taxes and fees
Cozy Haven: A Romantic Retreat in our Tiny House!
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.
Modern penthouse suite in a restored grain tower with private roof deck.
10.0 out of 10, Exceptional, (26)
"Wonderful stay!"
United States
Lisi M.
$478 nightly
The price is $540
Nov 4 - Nov 5
Total with taxes and fees
Modern penthouse suite in a restored grain tower with private roof deck.
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
9.8 out of 10, Exceptional, (19)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
United States
Cindy B.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Exterior
Walk to WP Gate + Free Parking!
Walk to WP Gate + Free Parking!
9.8 out of 10, Exceptional, (19)
"Well equipped space and great communication from the host"
United States
Beth
$287 nightly
The price is $318
Nov 17 - Nov 18
Total with taxes and fees
Walk to WP Gate + Free Parking!
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
$299 nightly
The price is $330
Nov 17 - Nov 18
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
6.8 out of 10, (5)
$999 nightly
The price is $1,130
Nov 4 - Nov 5
Total with taxes and fees
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Children's area
Hickory on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"We stayed one night. Would loved to have stayed longer. Beautiful property. "
United States
Christine B.
$586 nightly
The price is $668
Nov 4 - Nov 5
Total with taxes and fees
Hickory on Willow Lake
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4
Cabin in the heart of the Hudson Valley, Cabin 4
9.2 out of 10, Wonderful, (25)
"Great place to stay for a Beacon/Newburgh trip if you have a car, or like me, don’t mind hilly bike ride to and from. Cozy and affordable. "
United States
Derek L.
$149 nightly
The price is $176
Nov 4 - Nov 5
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
Interior
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
9.8 out of 10, Exceptional, (13)
"The property was perfect for what we were looking for. Secluded but not too far from hiking and lake activities. Very spacious and comfortably held our group of 11. Highly recommend."
United States
Matthew C.
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
9.6 out of 10, Exceptional, (15)
"Lovely two weeks in the carriage house on the Croton River. Hosts Patrick and Kathryn were attentive and helpful, the area was full of fun adventures for my husband, a cyclist, and me (jogger and kayaker). Swimming in the Croton from the dock was so great, especially on warm days. Kayaking in the Croton was peaceful and full of fun water birds."
United States
Ann M.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
10.0 out of 10, Exceptional, (2)
"Location was fantastic - short short walk (100-300’) to a handful of very good restaurants. The apartment is brand new, extraordinarily clean, well provisioned and has everything you could possibly need. It’s clear that the owners take pride in their property and take care of it accordingly. They are also super responsive and helpful. I accidentally locked myself out of the apartment one morning and "
United States
Ryan B.
$207 nightly
The price is $236
Nov 4 - Nov 5
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, 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 Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Nice and quiet "
Yoan 2-night trip
Posted 13 hours ago
Hampton Inn Harriman Woodbury

Find out more about Highland Mills

Everything you need to know about Highland Mills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Mills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Mills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Mills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Mills. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Mills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $176 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Mills rentals

At Expedia, we put the best Highland Mills vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland Mills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Mills vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Mills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

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 LEGOLAND® New York, or get outside and enjoy nature at Arrow Park Lake and Lodge. 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.