A calm lake at sunset with trees and grass along the shore.

Highland Mills Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Highland Mills vacation rentals

Private kitchen

1. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very Good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is ￥55,879
￥131,432 total
includes taxes & fees
Aug 1 - Aug 2
Perfect and Spacious Hudson Valley Escape!
House | 5 bedrooms

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ￥140,261
￥233,223 total
includes taxes & fees
Aug 4 - Aug 5
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.6 out of 10, Excellent, (8 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is ￥108,535
￥190,764 total
includes taxes & fees
Aug 3 - Aug 4
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior

4. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is ￥34,798
￥44,396 total
includes taxes & fees
Aug 4 - Aug 5
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Exterior

5. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is ￥16,759
￥31,598 total
includes taxes & fees
Aug 2 - Aug 3
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Smart TV, video games, DVD player, books

6. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is ￥33,327
￥64,221 total
includes taxes & fees
Aug 6 - Aug 7
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Dining

7. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥42,903
￥75,904 total
includes taxes & fees
Aug 7 - Aug 8
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Desk, WiFi (free), bed sheets

8. '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 ￥21,835
￥45,601 total
includes taxes & fees
Aug 2 - Aug 3
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Exterior detail

9. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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 ￥34,415
￥88,223 total
includes taxes & fees
Aug 4 - Aug 5
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Interior

10. Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
Ossining
6.0 out of 10, (1 review)
"We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. "
United States
Nada S.
The price is ￥36,551
￥46,528 total
includes taxes & fees
Aug 30 - Aug 31
Polished 1BR w/ Accessible Room Features + Sauna
Coffee/tea maker, fridge, microwave, oven

11. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥35,912
￥67,363 total
includes taxes & fees
Aug 4 - Aug 5
Contemporary Cozy Cottage
Exterior

12. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"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."
United States
Doria W.
The price is ￥79,007
￥113,229 total
includes taxes & fees
Aug 4 - Aug 5
Chestnut on Willow Lake
Exterior

13. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥48,282
￥73,066 total
includes taxes & fees
Aug 5 - Aug 6
Rustic Cabin in Fishkill!
Property grounds

14. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is ￥83,396
￥118,992 total
includes taxes & fees
Aug 5 - Aug 6
Red Cottage - Lakeside Property!
Exterior

15. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Nice place to stay"
United States
Anonymous traveler
The price is ￥14,432
￥16,686 total
includes taxes & fees
Aug 28 - Aug 29
1 Queen Bed | Non-Smoking, Kitchen
1 bedroom, WiFi (free)

16. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥17,638
￥19,951 total
includes taxes & fees
Aug 28 - Aug 29
2 Queen Beds | Non-Smoking, Kitchen
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (73 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is ￥39,503
￥52,321 total
includes taxes & fees
Aug 26 - Aug 27
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
TV

18. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥25,641
￥43,725 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail

19. West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking

West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Highland Falls
9.4 out of 10, Exceptional, (29 reviews)
"Our stay was excellent! Extremely clean, everything we needed. Walkable to everything in town. Great communication work h Host. We will definitely be staying again. "
United States
Joelle M.
The price is ￥51,873
￥84,502 total
includes taxes & fees
Aug 3 - Aug 4
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
TV

20. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is ￥52,791
￥81,655 total
includes taxes & fees
Aug 31 - Sep 1
Walk to WP Gate + Free 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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"The staff was very friendly and helpful. Room was clean and spacious."
Lisa 1-night trip
Posted 11 hours ago
Crowne Plaza Suffern - Mahwah by IHG

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:

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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 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?

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 7 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.