An aerial view of a lakeside community surrounded by autumn-colored trees.

Highland Lakes Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Highland Lakes holiday rentals

Desk, free WiFi, individually furnished, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is S$320
includes taxes & fees
20 Jul - 21 Jul
Cottage Suites
Private kitchen

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is S$789
includes taxes & fees
19 Jul - 20 Jul
Carriage House Apartment Goshen NY
Interior

Hike, Ski & Explore: Otisville Retreat w/ Yard!

Hike, Ski & Explore: Otisville Retreat w/ Yard!
3.0 star property
Otisville
The price is S$1,020
includes taxes & fees
20 Jul - 21 Jul
Hike, Ski & Explore: Otisville Retreat w/ Yard!
Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is S$667
includes taxes & fees
6 Aug - 7 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Lakes Hotel Reviews

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

8/10 Good
"Room was clean, staff was friendly, the pool was nice for having toys for kids and towels but it had some globbs of hair and a weird smell/taste of you got water near or in your mouth. It wasn't like normal pool chlorine.. but the kids had fun regardless. It worked for us to stay for one night after going to a water park near by."
Kristina 1-night trip
Posted 3 hours ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Frequently asked questions

Can I find holiday rentals in Highland Lakes?

Yes, there are holiday rentals close to the most popular sights in Highland Lakes, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Highland Lakes?

Choose from 11 Expedia holiday rentals in Highland Lakes for a memorable holiday.

What can I see and do in Highland Lakes?

Highland Lakes Beach 2 and Highland Lakes Beach 1 are a couple of lovely local spots to get outside and enjoy nature. Wawayanda State Park and Highland Lake are other places to visit while you're in town.

What are holiday rentals like in Highland Lakes?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Lakes. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.