You'll have the entire home to yourself and will only share it with other guests in your party.
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland
The Highlands - Private 5-Unit Estate perfect for extended families or groups – your exclusive retreat in the heart of the Catskills!
✔ 5 Private Units (2 houses + 3 cabins) ✔ Sleeps 30+ – Great for big families & groups ✔ Private Pool, Game Room, Open Spaces ✔ Near Kosher Dining & Local Attractions ✔ Fresh mountain air, privacy & room to relax
Enjoy the entire estate to yourselves – perfect for reunions, holidays, or peaceful getaways. Escape to fresh air! The space Escape to Your Private Catskills Retreat! Welcome to The Highlands—a charming, spacious, and completely private mini-colony nestled in the heart of the scenic Catskill Mountains. Ideal for large families, multiple families vacationing together, or group getaways, this exclusive rental offers your group full access to the entire estate—five units in total, all just for you! Ideal for reunions, retreats, or large family getaways.
A Cozy & Private Retreat Enjoy the warmth and charm of two country homes and three newly remodeled cabins, all enclosed within a classic white fence for ultimate privacy.
The estate comfortably accommodates large groups with: ^ 12 Bedrooms | Sleeps 30+ ^ 2 Country Homes + 3 Cottages ^ 2 Fully Equipped Kitchens + Modern Dining Area (seats 30–40 guests) ^ Game Room with pool, ping pong & foosball ^ Outdoor Fun – Pool, trampoline, fire pit & grassy yard ^ 2 Cozy Living Rooms with ample seating ^ Smart TVs, futons, Wi-Fi & stocked kitchens ^ Includes linens, towels, pots & more
ABOUT US: A Unique Colony-Style Getaway Designed like a private colony, The Highlands features five family-friendly units, making it a perfect choice for multi-family vacations, reunions, or group getaways. You'll have the entire property to yourselves!
2 houses each feature a master bedroom with 2 Queen size beds and en-suite bathroom, 2 additional bedrooms with 7 more beds, a kitchen, dining room and living room room. * Unit B features a Game Room downstairs with a chic pool table, foosball tables and games too. * Unit A hosts the large modern dining room area which seats large groups.
3 Cabins - Each with 2 bedrooms, a full bathroom, a living room with a futon couch, and updated interiors
You'll enjoy the entire estate to yourselves—no shared spaces, just your group’s private getaway.
Endless Fun & Relaxation Your group will love the variety of on-site amenities, including: ✔ Game Room with a pool table, ping pong, foosball, and lounging space ✔ Refreshing private pool (available in summer) ✔ Large grassy yard—perfect for kids to run and play ✔ Trampoline for outdoor fun ✔ Firepit area for relaxing evenings under the stars ✔ Lawn chairs and outdoor seating throughout the property
Prime Location Located just minutes from the best local attractions: *Resorts World Casino *Kartrite Indoor Waterpark *Holiday Mountain Ski & Snow Tubing Park *Hiking, fishing, and outdoor adventures
Enjoy amazing dining options, including kosher, nearby and explore the breathtaking beauty of the Catskills with ease.
Just a short walk to: ✔ Food, shops, & year-round kosher dining ✔ Local Shuls, Mikvah
Nature, Peace & Privacy Explore a peaceful mountain setting with grassy lawns, wildlife sightings, and rustic charm. You may spot deer, hear birds, or even see a shimmering spider web in the morning dew. It’s a real escape from city life—laid-back, quiet, and cozy.
Your Comfort & Safety Come First The property is located in a peaceful, private neighborhood, and for added security, exterior areas are monitored by five clearly visible closed-circuit cameras.
Fully Stocked & Ready for You The estate comes fully stocked with fresh linens, towels, cookware, and all the basics for a stress-free stay.
Whether you're escaping the noise of the city, planning a nature-filled family trip, or gathering friends for a cozy reunion, The Highlands offers a warm, rustic getaway that’s all your own.
Kick off your shoes, breathe in the mountain air, and experience the serenity of your own Catskills colony.
We look forward to hosting you soon—like so many of our happy returning guests!
----------- Guest access Exclusive Property Booking Details: For bookings up to 16 guests: Only the 2 front houses are included in your booking.
For 16-36 guests (or if you have 16 or fewer guests but would like all units included), please contact us for a custom quote to book all 5 units.
Feel free to reach out for any further information or special requests
Shul Access: - 4-minute walk in the summer; 10-minute walk year-round
The Perfect Getaway: Whether you're seeking outdoor adventure, family-friendly fun, or a peaceful retreat, Highland Estate Colony is the perfect destination to unwind and explore.
Property manager
Shira
Languages
English, French, Russian, Spanish
Add dates for prices
Property amenities
Ski
Close to skiing
Snowboarding nearby
Pool/Spa
Outdoor pool
Private pool
Internet
Available in the house: Free WiFi
Parking and transportation
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Electric kettle
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
Toaster
Dining
Dining table
Bedrooms
12 bedrooms
Bedsheets provided
Bathroom
7 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Separate dining area
Entertainment
Books
Games
Smart TV
Outdoor areas
Barbecue grill
Firepit
Garden
Outdoor furniture
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming dogs only
3 pets total (up to 20 lbs per pet)
Suitability/Accessibility
Smoking not allowed
Services and conveniences
Iron/ironing board
Location highlights
In a rural location
In a village
In the mountains
Near a health/beauty spa
Near a hospital
Near an outlet shopping mall
Things to do
Arcade/game room
Billiards/pool table
Foosball table
Table tennis
Water park
Birdwatching nearby
Casino nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Horseback riding nearby
Hunting nearby
Ice skating nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Mountain biking nearby
Mountain climbing nearby
Rock climbing nearby
Sledding nearby
Snowmobiling nearby
Swimming nearby
Theme park nearby
Water tubing nearby
Wildlife walks nearby
Winery tours nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Pets
Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
3 total (up to 20 lbs per pet)
Children and extra beds
Children are welcome
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 40
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the neighborhood
Monticello, NY
What's nearby
Monticello Casino and Raceway - 3 min drive - 1.8 km
Resorts World Catskills - 6 min drive - 6.1 km
Concord Monster Golf Course - 8 min drive - 7.5 km
Monticello Motor Club - 9 min drive - 8.1 km
The Kartrite Resort & Indoor Waterpark - 9 min drive - 6.1 km
Restaurants
McDonald's - 4 min drive
Good Friends - 10 min drive
Tilly's Diner - 2 min drive
Doubletop Bar & Grill - 10 min drive
Burger King - 4 min drive
Frequently asked questions
Does Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland have a pool?
Yes, this property has an outdoor pool.
Is Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland pet-friendly?
Yes, this property allows dogs (limit 3 total) with a maximum weight of up to 20 lbs per pet.
What time is check-in at Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland?
Check-in begins at 4:00 PM.
What time is check-out at Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland?
Check-out is at 11:00 AM.
Where is Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland located?
This family-friendly Monticello vacation home is located in the mountains, 1.7 mi (2.8 km) from Monticello Casino and Raceway, and within 6 mi (10 km) of The Kartrite Resort & Indoor Waterpark and Mongaup River. Concord Monster Golf Course and Monticello Motor Club are also within 6 mi (10 km).
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Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 2 out of 2 reviews
10 - Excellent
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Rating 6 - Okay. 0 out of 2 reviews
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2 - Terrible
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10/10
Cleanliness
Reviews
10/10
The property was very big and spacious. We had a large group, yet everyone had more than enough room.Looking forward to renting this place again.
Kristian M.
Stayed 2 nights in Jun 2025
10/10
We had the most incredible stay at Highland! This property is perfectly set up for groups or families traveling together. With five separate houses/cabins, each couple (and their kids) had their own private space to relax and recharge—super comfortable and cozy, yet very clean and well-kept. It made the whole experience feel seamless and stress-free.At the same time, the shared space was perfect for gathering. We had the best time cooking and eating meals together, playing games, and just enjoying each other’s company in the inviting common areas. The setup gave us that rare mix of togetherness and personal space.The property has such a charming country feel—peaceful, quiet, and surrounded by nature. We especially loved the beautiful yard, which felt like our own private family estate. Whether we were sipping coffee in the morning sun or just sitting out and chatting while the kids played, it was the kind of place that makes you slow down and soak it all in.And the host was absolutely wonderful—kind, responsive, and clearly dedicated to making sure everything runs smoothly. It really felt like staying at a home away from home.The location was also ideal—so close to everything, but with a peaceful, tucked-away vibe that made us feel like we were far from it all.If you’re planning a group getaway, family reunion, or retreat, Highland is truly a gem. We made amazing memories and can’t wait to come back!