Photo by Karen Wirtz

Holiday Rentals in Highland Lakes

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Our top choices for Highland Lakes holiday rentals

10.0 out of 10, Exceptional, (6)
"Cozy property with privacy and comfort. "
United States
Anonymous traveller
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries
10.0 out of 10, Exceptional, (35)
"Wonderful place and cozy will book again "
United States
Alex P.
The price is €360
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
The price is €221
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
8.6 out of 10, Excellent, (92)
"Nice unit. I stay here once a year for a golf event."
United States
Kevin M.
The price is €390
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
10.0 out of 10, Exceptional, (70)
"We had a great stay."
United States
Laura
The price is €253
includes taxes & fees
21 Dec - 22 Dec
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
10.0 out of 10, Exceptional, (27)
"Wonderful stay!"
United States
Lisi M.
The price is €503
includes taxes & fees
18 Jan - 19 Jan 2026
Modern penthouse suite in a restored grain tower with private roof deck.
9.4 out of 10, Exceptional, (45)
"Beautiful area"
United States
Joseph D.
The price is €265
includes taxes & fees
20 Dec - 21 Dec
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.8 out of 10, Exceptional, (8)
"Awesome place. Cozy and great communication with owners. "
United States
Dominick P.
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.
6.8 out of 10, (5)
"It was a great home with lots of space indoor and outside. "
United States
Yogita R.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
6.8 out of 10, (11)
"we enjoyed the cozy home it is a nice place to get away"
United States
Yidel
Cozy Haven: A Romantic Retreat in our Tiny House!
2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is €374
includes taxes & fees
19 Dec - 20 Dec
Stylish & Peaceful Getaway on 3 Private Acres
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
9.8 out of 10, Exceptional, (173)
"All good. Can be a little noisy because it is two floors above lounge/bar but otherwise all as hope and expected. Quick answer to one question we had. "
United States
Alan
Located next to the Ski Resort, Bike Park and Water Park
8.4 out of 10, Very good, (24)
"It was a very short distance to Mtn Creek for the race weekend "
United States
Daniel G.
The price is €322
includes taxes & fees
22 Dec - 23 Dec
Mountain Creek/Great Gorge Village 2 Bedroom Condo W/Loft
10.0 out of 10, Exceptional, (30)
"Beautiful property, the photos do it justice, but the location (and peace) of the property can't be seen in just pictures. The family agreed one of the best places we've gotten, wonderful way to spend a late summer week on the lake."
United States
Devan S.
The price is €446
includes taxes & fees
14 Jan - 15 Jan 2026
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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 €411
includes taxes & fees
11 Jan - 12 Jan 2026
Serene Rustic Retreat with Lake
9.4 out of 10, Exceptional, (56)
"The house was so comfortable and had everything we needed to catch up over our girl's weekend. The porches and the living room were both excellent gathering spaces and we loved being so close to the spa. You can't beat the location and the house was lovely! The owners were also really responsive to questions we had over our stay. "
United States
Cailyn M.
The price is €444
includes taxes & fees
23 Dec - 24 Dec
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
9.8 out of 10, Exceptional, (89)
"We loved our stay! This house was perfect for our family (6 adults) 3 teenagers. Everyone had their own space, the backyard was our favorite place to hang. Close to waterpark. Tennis court was a big bonus! We can’t wait to come back during the winter for a snowboard trip! "
United States
Meagan B.
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is €254
includes taxes & fees
2 Jan - 3 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (5)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
United States
Sol K.
The price is €714
includes taxes & fees
14 Jan - 15 Jan 2026
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
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 Lakes Hotel Reviews

Find out more about Highland Lakes

Everything you need to know about Highland Lakes 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 Lakes holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Lakes holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland Lakes holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Lakes. 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 Lakes 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 Lakes holiday rentals we have selected for you start as low as €221 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland Lakes rentals

At Expedia, we put the best Highland Lakes 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 Lakes 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 Lakes 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 Lakes. 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 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.

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

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This holiday home rental outside of Highland Lakes offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Highland Lakes?

Choose from 9 Expedia holiday rentals in Highland Lakes for a memorable holiday.

What can I see and do in Highland Lakes?

Highland Lakes Beach 1 and Highland Lake are a couple of lovely local spots to get outside and enjoy nature. Wawayanda Lake and Wawayanda State Park 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.