Photo by Ginie Ying

Town of Highland holiday rentals

We found 521 holiday rentals — enter your dates for availability

Discover a selection of 28 homes and other holiday rentals in Town of Highland that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Popular Town of Highland destinations on Stayz

A solitary tree in a misty field with a backdrop of a cloudy sky and dense forest.

Eldred

A calm lake surrounded by dense green forest under a partly cloudy sky.

Barryville

Holiday rentals with weekly discounts – Town of Highland

Showing deals for:6 Nov - 13 Nov

High ceilings and lake views in this gorgeous living room

Exceptional

(5 reviews)

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Forestburgh

16% off

AU$5,033

for 7 nights, 1 chalet

AU$719 per night

includes taxes & fees

Dining and front TV room with beautiful outdoor view of the mountains

Living or TV area at front entrance of cabin

Wonderful

(7 reviews)

The Luxury Cabin at Deep Hollow

Narrowsburg

16% off

AU$6,025

for 7 nights, 1 cabin

AU$861 per night

includes taxes & fees

Exceptional

(7 reviews)

lake/fireplace

Greeley

9% off

AU$51,671

for 7 nights, 1 home

AU$7,382 per night

includes taxes & fees

Exceptional

(41 reviews)

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Monticello

7% off

AU$6,366

for 7 nights, 1 villa

AU$909 per night

includes taxes & fees

Exceptional

(117 reviews)

Masthope modern log-cabin sided retreat!

Lackawaxen

7% off

AU$3,534

for 7 nights, 1 chalet

AU$505 per night

includes taxes & fees

Exceptional

(26 reviews)

Private log cabin nestled at the base of a secluded wooded area

Yulan

8% off

AU$5,719

for 7 nights, 1 home

AU$817 per night

includes taxes & fees

Redesigned safe and well lit staircase and path.

The main living area showing living room, dining area and kitchen.

Peaceful & Quiet Winter Retreat. Enjoy a warm fire and view the iced over lake.

Exceptional

(204 reviews)

Relaxing Lakefront, Very Clean. Great for Families.

Bethel

9% off

AU$4,197

for 7 nights, 1 home

AU$600 per night

includes taxes & fees

Heated pool open from Memorial Day Weekend thru the end of September

Excellent

(13 reviews)

Casa Nera | Heated Pool • Hot Tub • Ski • Golf

Swan Lake

15% off

AU$4,631

for 7 nights, 1 home

AU$662 per night

includes taxes & fees

Exceptional

(6 reviews)

Cozy Catskills Farmhouse in Barryville near the Delaware River

Barryville

7% off

AU$2,976

for 7 nights, 1 home

AU$425 per night

includes taxes & fees

Exceptional

(20 reviews)

Cozy Cabin at Big Bear Mountain: Pools, Lake, Ski, Horseback & More at Masthope!

Lackawaxen

10% off

AU$2,458

for 7 nights, 1 cabin

AU$351 per night

includes taxes & fees

Exceptional

(108 reviews)

Luxury Chalet Masthope Near Narrowsburg & Delaware

Masthope

7% off

AU$5,489

for 7 nights, 1 home

AU$784 per night

includes taxes & fees

Exceptional

(9 reviews)

Elegant 19th-Century House in a Hamlet on the Delaware River

Narrowsburg

16% off

AU$6,955

for 7 nights, 1 home

AU$994 per night

includes taxes & fees

Very good

(27 reviews)

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Monticello

8% off

AU$9,098

for 7 nights, 1 home

AU$1,300 per night

includes taxes & fees

Exceptional

(11 reviews)

Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.

Narrowsburg

12% off

AU$3,300

for 7 nights, 1 home

AU$471 per night

includes taxes & fees

Exceptional

(32 reviews)

Cozy Retreat in Masthope by Narrowsburg & Delaware

Lackawaxen

7% off

AU$3,085

for 7 nights, 1 home

AU$441 per night

includes taxes & fees

Exceptional

(9 reviews)

Mountain Retreat Masthope-Ski-Boat-Swim. Walk to ski slopes-pools - Pet Friendly

Lackawaxen

11% off

AU$3,136

for 7 nights, 1 home

AU$448 per night

includes taxes & fees

Exceptional

(12 reviews)

Completely renovated house in amenities-filled Masthope community / Ski Big Bear

Lackawaxen

7% off

AU$2,526

for 7 nights, 1 home

AU$361 per night

includes taxes & fees

Exceptional

(5 reviews)

Stylish 2-Bedroom Ski/Lake House in Masthope Mountain Community

Lackawaxen

8% off

AU$2,786

for 7 nights, 1 home

AU$398 per night

includes taxes & fees

Keyless entry and exterior security camera

Exceptional

(13 reviews)

The Perfect Catskills Lake House

Yulan

8% off

AU$4,279

for 7 nights, 1 home

AU$611 per night

includes taxes & fees

Exceptional

(54 reviews)

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello

7% off

AU$6,994

for 7 nights, 1 home

AU$999 per night

includes taxes & fees

Exceptional

(18 reviews)

Enjoy the Magic of the Catskills in your Private Lakefront Home

White Lake

7% off

AU$3,078

for 7 nights, 1 home

AU$440 per night

includes taxes & fees

Exceptional

(11 reviews)

The Castle on the Hill

Shohola

8% off

AU$1,288

for 7 nights, 1 apartment

AU$184 per night

includes taxes & fees

Private lakefront deck for sunrise coffee, afternoon lounging & sunset cocktails

Gather around the kitchen island for breakfast, wine, or shared meals

Original Victorian staircase that preserves the home’s historic charm

Exceptional

(8 reviews)

Victorian Lake Oasis | Hot Tub | Private Lakefront

Damascus

7% off

AU$3,119

for 7 nights, 1 home

AU$446 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Town of Highland

Premier Host

Private log cabin nestled at the base of a secluded wooded area

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

ESCAPE-REFRESH-Large Riverfront Estate-Pristine, Private, Fresh Air-90miles GWB

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Amazing All-Season, Private Lakefront Retreat!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Indoor Pool, 7 bdrm, Designer Home, Hot Tub, Stunning Kitchen

Sleeps 18 · 7 bedrooms · 5+ bathrooms

Premier Host

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

Sleeps 3 · 1 bedroom · 1 bathroom

Enchanting River - Waterfront A Frame Cabin

Sleeps 6 · 2 bedrooms · 1 bathroom

Choose a holiday rental for your Town of Highland getaway

Learn about the unique charm of Town of Highland with a stay in a holiday home rental. This city has something for everyone. Bethel Woods Center For The Arts and Lake Wallenpaupack are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Town of Highland

Do you want to discover things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Town of Highland a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

Lake Wallenpaupack (19 mi / 30.5 km)
Ski Big Bear at Masthope Mountain (6.3 mi / 10.2 km)
Monticello Motor Club (12.1 mi / 19.4 km)
Costa's Family Fun Park (13.8 mi / 22.1 km)
Soarin Eagle Rail Tours (15.3 mi / 24.6 km)
Concord Monster Golf Course (16.1 mi / 25.9 km)

Exploring the natural landscape of Town of Highland

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Town of Highland is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Lake Wallenpaupack (19 mi / 30.5 km)
Mohican Lake (4.4 mi / 7 km)
Lackawaxen River (5.7 mi / 9.2 km)
Fawn Lake (9.1 mi / 14.6 km)
Lake Superior State Park (9.7 mi / 15.5 km)
Tusten Veterans Memorial Park (10.1 mi / 16.2 km)

Frequently asked questions

What is the best area to stay in Town of Highland when booking a holiday home?

If you're on your way to Town of Highland, Barryville is regarded as one of the most sought-after locations to spend a holiday. While you're here, keep busy by exploring wonderful sights like Minisink Battlefield County Park and Brook House Gallery Incorporated.

What is the most popular type of holiday home accommodation in Town of Highland?

Based on our research, houses are considered the most popular property type in Town of Highland. But naturally, everyone's idea of an awesome trip will differ. Stayz has holiday homes with every size, shape and budget in mind, so you're sure to discover your perfect match.

How much does it cost to rent a holiday home in Town of Highland?

Season, length of stay and property type are some factors that can determine the price of a holiday home. Simply add your dates of travel to find your dream escape. From cosy cabins to expansive villas, all Stayz holiday homes offer amazing value.

How much does it cost to rent a beach house in Town of Highland?

When you travel and the style and size of the property will determine the cost of your beachside escape. Click on your Town of Highland travel dates to view your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the amenities and features you need.

Are there pet-friendly holiday homes in Town of Highland?

You're in luck. There are. Choose from 30 stays that welcome pets in Town of Highland on Stayz. Our cuddly best friends also need a break, so simply use our search function for pet-friendly holiday homes to find a property where your puppy can join in the fun.

What are popular home amenities in Town of Highland?

When it comes to home amenities that people prefer in Town of Highland, a sauna, a nearby river and a barbecue grill are at the top of the list. With Stayz holiday homes, you'll enjoy options to match your style and taste, whether you're on a trip with family, friends or even pets.

Are there large group holiday homes in Town of Highland?

With eight holiday homes that can sleep 10 or more people in Town of Highland, you don't have to leave anyone off your invite list. From holidays with the extended family to special events like Christmas and birthday parties, Stayz will help you find a large group home to match the occasion.

Are there holiday homes in Town of Highland that welcome kids?

With 30 family-friendly holiday homes to select from in Town of Highland, now is a superb time to introduce your kids to the pleasures of travel. Simply click on our "Properties good for families" filter box to locate stays that come with amenities perfect for travelling families, such as living rooms, backyards, hot tubs and bunk beds.

What are the top attractions for families in Town of Highland?

Keep the kids occupied at these leading family-friendly attractions in Town of Highland:

Fort Delaware Museum
Ski Big Bear at Masthope Mountain
Mohican Lake

Are there one-bedroom holiday homes in Town of Highland?

You can pick from four one-bedroom homes in Town of Highland. Whether you're searching for a cosy chalet or a condo, Stayz's one-bedroom properties are great if you don't require lots of space. One of the perks of having your own pad? You won't ever need to share your trip with strangers.

Can I find two-bedroom holiday homes in Town of Highland?

You can select from five two-bedroom holiday properties in Town of Highland. Put the kids in the second room or maybe fill it with a couple of your best friends. There's a spot for whoever's lucky enough to be joining your journey.

Are there holiday homes with WiFi in Town of Highland?

Pick from 19 holiday homes with WiFi in Town of Highland. If you'd like to disconnect from the world on your trip, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Town of Highland?

Decide on your travel dates and then use the filter tool to see holiday homes with ac in Town of Highland on Stayz. With 23 air-conditioned properties available here, you can enjoy a cool and comfy stay.

How old do you have to be to rent a holiday home in Town of Highland?

Age restrictions can differ between properties on Stayz, so look at the rules of the holiday home in Town of Highland you want to book. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Town of Highland for?

It all depends on the Town of Highland property. To see all available options offering extended stays, simply type your dates and number of people into Stayz. Look forward to having the whole property to yourself, as well as amenities such as a fully-equipped kitchen and a backyard to run around in. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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