Highland Lake Holiday Rentals

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Our top choices for Highland Lake holiday rentals

10.0 out of 10, Exceptional, (33)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is NZ$1,334
includes taxes & fees
5 Jan - 6 Jan 2026
Lakefront | Sport Courts | HotTub | GameRoom
2.0 star property
The price is NZ$1,481
includes taxes & fees
5 Jan - 6 Jan 2026
2 Lake Cabins Pool+hottub Game Room 23acs

Holiday Home in Highland Lake

Sweet Old Farmhouse in a Tranquil Setting
3.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"
United States
Anne H.
The price is NZ$545
includes taxes & fees
17 Jan - 18 Jan 2026
Sweet Old Farmhouse in a Tranquil Setting
10.0 out of 10, Exceptional, (9)
"The owner was very kind and helped us with directions and recommendations for eateries around the area. "
United States
Jody
The price is NZ$523
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Cabin with Fireplace, Firepit, Close to Lake
3.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent Vacaciones Places Instagram and Facebook recommended your Property "
United States
Ronny
15 Mi to Ski Big Bear: Gem w/ Deck & Game Room

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is NZ$711
includes taxes & fees
31 Dec - 1 Jan 2026
Hello Small Stone
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
The price is NZ$506
includes taxes & fees
11 Jan - 12 Jan 2026
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
10.0 out of 10, Exceptional, (4)
"Lovely quaint stay!"
United States
Kelly G.
Couple's Serenity Cabin * Hot Tub *Lake

Cabin in Cuddebackville

Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is NZ$824
includes taxes & fees
3 Jan - 4 Jan 2026
Serene Rustic Retreat with Lake

Chalet in Narrowsburg

The Chalet - Rustic Retreat
9.0 out of 10, Wonderful, (11)
"Fantastic stay. Quiet area, close to Narrowsburg, friendly neighbors. Super clean, fire pit area is very nice and we love the hot tub after a day on the river!"
United States
Jeff H.
The price is NZ$610
includes taxes & fees
4 Jan - 5 Jan 2026
The Chalet - Rustic Retreat

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is NZ$373
includes taxes & fees
4 Jan - 5 Jan 2026
Trails Head Cabin

Holiday Home in Liberty

Anthony's Castle
9.0 out of 10, Wonderful, (12)
"We enjoyed staying at Anthony’s Castle. It suited our needs - was clean & comfortable. Location was approx 20 minutes from Bethelwoods and we will stay here again in the future. "
United States
David
The price is NZ$447
includes taxes & fees
1 Jan - 2 Jan 2026
Anthony's Castle
10.0 out of 10, Exceptional, (22)
"Super clean and roomy. Comfortable bed. Good location."
United States
Alyssa E.
The price is NZ$422
includes taxes & fees
1 Jan - 2 Jan 2026
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled
9.2 out of 10, Wonderful, (5)
"An immaculately clean, comfortable and quiet house with spacious rooms and comfortable furnishings. The owners were super friendly and responsive to our needs. We hope to stay here again next year."
United States
Denise
The price is NZ$467
includes taxes & fees
8 Jan - 9 Jan 2026
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
3.0 star property
The price is NZ$527
includes taxes & fees
30 Dec - 31 Dec
Hike & Fish: Outdoor Retreat Near Trails
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay. A nice quiet location. We had breakfast, lunch, and drinks and dinner on the little front patio. We will be coming back!! "
United States
June D.
The price is NZ$487
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail
10.0 out of 10, Exceptional, (2)
"Love the property and the house was very nice clean"
United States
Atasha
Couple's Retreat Lodge|Hot Tub| RiverViews|Tennis

Holiday Home in Mongaup Valley

5 minutes from original Woodstock site.
9.8 out of 10, Exceptional, (61)
"Clean, cozy home. Located very close to the concert venue. "
United States
John C.
The price is NZ$608
includes taxes & fees
31 Dec - 1 Jan 2026
5 minutes from original Woodstock site.
10.0 out of 10, Exceptional, (6)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
The price is NZ$571
includes taxes & fees
12 Jan - 13 Jan 2026
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
2.0 star property
10.0 out of 10, Exceptional, (5)
"The Clock House was just what we needed for a long weekend with our two pups. We appreciated a spotless home, well appointed kitchen, super comfy king bed and being a short walk into town. The pups appreciated the fireplace, the dog bed and the bird feeder right outside the window. Would gladly stay here again! "
United States
Julie C.
The price is NZ$911
includes taxes & fees
21 Jan - 22 Jan 2026
Beautiful Riverside w/ Sunroom, FP, Walk to Town!
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 Lake Hotel Reviews

Find out more about Highland Lake

Everything you need to know about Highland Lake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Lake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Lake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland Lake holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland Lake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Lake holiday rentals we have selected for you start as low as NZ$373 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland Lake rentals

At Expedia, we put the best Highland Lake holiday 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 Lake 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 Lake holiday.

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 Lake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Highland Lake?

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

What are some of the best holiday rentals that Highland Lake has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Highland Lake is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Highland Lake?

Choose from 6 Expedia holiday rentals in Highland Lake for a memorable holiday.

What can I see and do in Highland Lake?

While exploring the area, visit family-friendly sights like The Kartrite Resort & Indoor Waterpark, or get outside and enjoy nature at Sidwell Lake. In the wider area, you’ll find Mohican Lake and Kadampa Meditation Center New York and World Peace Temple.

What are holiday rentals like in Highland Lake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Lake. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.