Highland Mills Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Highland Mills

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, (122)
"It has an incredible mountain and water view. "
The price is HK$1,463
HK$2,386 total
includes taxes & fees
13 Oct - 14 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Outdoor dining

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
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

9.6 out of 10, Exceptional, (39)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is HK$2,016
HK$2,588 total
includes taxes & fees
2 Nov - 3 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Chestnut on Willow Lake
Dining tables

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is HK$3,113
HK$4,528 total
includes taxes & fees
13 Oct - 14 Oct
Chestnut on Willow Lake
The Woodbury Cottage
Property grounds

The Woodbury Cottage

9.0 out of 10, Wonderful, (26)
"A cozy place to stay. "
The Woodbury Cottage
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Outdoor banquet area

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8.8 out of 10, Excellent, (5)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is HK$6,569
HK$10,964 total
includes taxes & fees
16 Oct - 17 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is HK$1,506
HK$3,861 total
includes taxes & fees
14 Oct - 15 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Houseboat Paradise Vacation
Interior

Houseboat Paradise Vacation

2.0 star property
The price is HK$3,308
HK$5,249 total
includes taxes & fees
16 Oct - 17 Oct
Houseboat Paradise Vacation
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is HK$1,775
HK$2,784 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
Walk to WP Gate + Free Parking!
Exterior

Walk to WP Gate + Free Parking!

9.8 out of 10, Exceptional, (18)
"Great property and the hosts were very communicative."
The price is HK$1,536
HK$2,354 total
includes taxes & fees
27 Oct - 28 Oct
Walk to WP Gate + Free Parking!
A luxurious stay.
Smart TV

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is HK$981
HK$2,280 total
includes taxes & fees
12 Oct - 13 Oct
A luxurious stay.
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

9.0 out of 10, Wonderful, (14)
"Very cozy stay with responsive host"
The price is HK$3,152
HK$5,305 total
includes taxes & fees
12 Oct - 13 Oct
Large,Cozy,Bright Apartment, Business Themed.
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Smart TV, fireplace, books, computer monitors

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

10.0 out of 10, Exceptional, (2)
"From the moment we arrived, we knew we had picked a gem. The house is absolutely lovely—tastefully decorated, comfortable, and full of charm. Every room feels fresh and inviting, and it’s clear the owners take great pride in maintaining their space.Cleanliness was outstanding throughout. We were especially touched by how genuinely friendly and responsive the owner was. From our first inquiry to the check-out process, they were prompt, helpful, and always checked to make sure we were comfortable....
The price is HK$3,446
HK$6,866 total
includes taxes & fees
15 Oct - 16 Oct
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Exterior

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge
Greenwood Lake Lakefront Luxury
Property grounds

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (143)
"Lovely house with lake access. Had a great stay!"
Greenwood Lake Lakefront Luxury
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Games room

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

10.0 out of 10, Exceptional, (3)
"The property was spotless, comfortable, and had everything we needed. The location was perfect—close to attractions yet quiet and relaxing. The hosts were amazing, welcoming and very responsive, they were welling to help us at all times and they may made sure the whole experience was smooth and enjoyable. We’d definitely stay here again!"
The price is HK$2,132
HK$4,375 total
includes taxes & fees
15 Oct - 16 Oct
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Spectacular Mansion w/Pool&Tennis
Pool

Spectacular Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (13)
"House was perfect for a group of 16 people. Pool, tennis courts and lawn were incredible. Highly recommend and would return! "
Spectacular Mansion w/Pool&Tennis
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Spacious Bathroom "
David 1-night trip
Posted 14 hours ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Highland Mills

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
  • Use the map to find apartments and other holiday homes in the Highland Mills neighbourhood you prefer
  • 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in Highland Mills?

Yes, we give you a choice of holiday rentals where you'll be just 9.8 mi (15.8 km) from LEGOLAND® New York, giving you a secluded option to escape the hustle and bustle. 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 holiday rentals that Highland Mills has to offer?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Highland Mills is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Highland Mills?

Choose from 3 Expedia holiday rentals in Highland Mills for a memorable holiday.

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, Palaia Vineyards Winery and Schunnemunk State Park are other places worth a visit.

What’s a holiday rental in Highland Mills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland Mills. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.