Highland Mills Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Highland Mills

Cozy family-friendly home!
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
The price is CA $190
CA $391 total
includes taxes & fees
Jun 13 - Jun 14
Cozy family-friendly home!
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Fridge, microwave, oven, stovetop
Kick back & relax in this peaceful, stylish place to stay with the whole family.
10.0 out of 10, Exceptional, (12)
"Beautiful property, plenty of room! Clean, plenty of linens and other amenities As described. Would definitely recommend if needed for large family/friends to attend events in this area."
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Hudson Valley Getaway: Perfect for families and large groups
A heated pool
Hudson Valley Getaway: Perfect for families and large groups
9.4 out of 10, Exceptional, (9)
"I rented this property for my co-workers who were here for a retreat at my home in the area, and at the local community center. This home had everything we needed, and the host was easy to communicate with. We will definitely consider using this property again for future guests coming for work and family gatherings."
The price is CA $527
CA $1,081 total
includes taxes & fees
Jun 5 - Jun 6
Hudson Valley Getaway: Perfect for families and large groups
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Cottage Suites
Luxury Studio | Private kitchen
Cottage Suites
3.0 star property
8.0 out of 10, Very good, (1)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is CA $279
CA $393 total
includes taxes & fees
Jun 17 - Jun 18
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Lakefront Luxury on Greenwood Lake
Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (116)
"This is our second visited and we are still in love with the Lake House!"
Lakefront Luxury on Greenwood Lake
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (36)
"Very nice. A lot of attention to detail"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is CA $149
CA $223 total
includes taxes & fees
Jun 2 - Jun 3
Cabin in the heart of the Hudson Valley, Cabin 4
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is CA $149
CA $223 total
includes taxes & fees
Jun 3 - Jun 4
Cabin in the heart of the Hudson Valley, Cabin 2
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is CA $698
CA $1,323 total
includes taxes & fees
Jun 2 - Jun 3
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Spectacular Log Home Estate North Wing Apt
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Royal Garden Main Cabin
Interior
Royal Garden Main Cabin
Royal Garden Main Cabin
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (18)
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is CA $204
CA $395 total
includes taxes & fees
Jun 30 - Jul 1
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Beach
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (35)
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is CA $176
CA $317 total
includes taxes & fees
Jun 13 - Jun 14
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (62)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Don't see what you're looking for?
See all available properties in Highland Mills
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.

Other types of properties in Highland Mills you may be interested in

La Quinta Inn & Suites by Wyndham Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (388)
"The staff was nice. Checking in was very quick and the place is clean. "
The price is CA $173
CA $205 total
includes taxes & fees
Jun 5 - Jun 6
La Quinta Inn & Suites by Wyndham Middletown
HYATT house Fishkill/Poughkeepsie
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1001)
"N/A"
The price is CA $194
CA $217 total
includes taxes & fees
Jun 13 - Jun 14
HYATT house Fishkill/Poughkeepsie
DoubleTree by Hilton Hotel Nanuet
Lobby
DoubleTree by Hilton Hotel Nanuet
4.0 star property
8.4 out of 10, Very good, (1001)
"Nice staff and excellent service "
The price is CA $173
CA $193 total
includes taxes & fees
Jun 16 - Jun 17
DoubleTree by Hilton Hotel Nanuet
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.

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?

Cozy family-friendly home!: 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. Kitchen amenities include a fridge, a stovetop, and a microwave.

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?

Cultural attractions include United States Military Academy, whereas Schunnemunk State Park is a spot to enjoy nature. Woodbury Common Premium Outlets and LEGOLAND® New York are other popular places to visit in the area.

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.

Recent reviews of Highland Mills properties
Expedia verified reviews

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

5/5 Excellent
"Amazing experience. The staff, hotel all are excellent. "
A verified traveller stayed at Sleep Inn & Suites Monroe - Woodbury
Posted 14 hours ago
Sleep Inn & Suites Monroe - Woodbury