Highland Cabins Estate! Huge Hotub, 5 Private Units! Gameroom; 40+ guests

Monticello, New York
$1046 avg/night Minimum Stay 1 Nights
Bed 12

Bed

Bath 7

Bath

Home Private Vacation Home

Property Type

Sleep 46

Max Sleeps

Night 1 nights

Min Stay

The Highlands - Private 5-Unit Estate perfect for extended families or groups – your exclusive retreat in the heart of the Catskills!

Read the description, before you book for description and terms:

✔ 5 Private Units (2 houses + 3 cabins**)
✔ Sleeps 36+ – Great for big families & groups
✔ Huge Hotub, 9+ People -open all year round
✔ Private Pool, Game Room, Open Spaces
✔ Near Kosher Dining, Shul & Local Attractions
✔ Fresh mountain air, privacy & room to relax

Enjoy the entire estate just to yourselves – perfect for reunions, holidays, or peaceful getaways. Escape to fresh air!

Escape to Your Own 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 36+
^ 2 Country Homes + 3 Cottages**
^ 2 Fully Equipped Kitchens + Modern Dining Area (seats 40 guests)
^ Game Room with pool table, ping pong & foosball
^ Outdoor Fun – Pool, Hotub, 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 [It is one group at a time, even if not booking all units].

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.

These are cozy country homes and cabins—comfortable, inviting, and exactly as pictured, with the amenities and condition shown in the listing. If you’re looking for a relaxed country-style getaway, you’re in the right place. If you’re expecting red-carpet luxury, the Waldorf may be a better fit.

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!

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**Guest access
Exclusive Property Booking Details:
For bookings up to 16 guests: Only the 2 front houses are included in your basic booking.

For 16-36 guests (or if you have 16 or fewer guests but would like all 5 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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Close To Skiing
  • PETS

    3 Total (up To 20 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    12 Bedrooms Bed Sheets Provided
  • GENERAL

    Humane Treatment Of Captive Wild Animals Locally-owned & Organized Tours & Activities Recycling Uses Some LED Lighting Water-efficient Showers Only
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Microwave Oven Paper Towels Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Garden Outdoor Furniture Patio
  • POOL/SPA

    Hot Tub Outdoor Pool Private Pool
  • BATHROOMS

    7 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English French Russian Spanish
  • THINGS TO DO

    Fishing Nearby Fitness Facilities Nearby Golf Nearby Hiking Nearby Kayaking Nearby Mountain Biking Nearby Mountain Climbing Nearby Power Boating Nearby Sledding Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Foosball Table Games Pool Or Billiards Table Table Tennis Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Games Children's Toys Highchair Playground Travel Crib
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village In The Mountains Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 46

Map Map

School District Rates & Availability

Review Review

  • Shripad U.

    Submitted Jan 11, 2026

    Stayed Dec 30, 2025

    We booked this property as our 31st eve gate-away for 7 families (including kids and toddlers) and paid very hefty price for this below average property)This house is pretty much dated and old so it has a typical foul smell in all the units especially the one main ones where you have kitchen and living room.This property has 5 different units as rightly listed.We checked in around 4 pm on Dec 30th.To our surprise pathways were full of Black Ice (snow turned into ice) as snow was not removed at all from pathways, It was very slippery if you are walking from one unit to another. It was never cleared through out our check out despite several calls, messages to the Host (Shira). We had several accidents during our stay due to that. The water/drain pipe was frozen in one of the unit (2 bedrooms) and had no water so we were unable to use that. In another unit toilet flush was not working so that was also unusable. The response time is very poor & these issues were not resolved until check out. Nails protruding from doors and walls which is very risky especially if you have kids. Heater panels and controls were broken. Extremely poor lights in the bedrooms so at night it is almost dark in the bedrooms.we shared everything on email via photos/videos and asked for refund but no response from Host/Shira.

  • Nancy D.

    Submitted Oct 6, 2025

    Stayed Oct 4, 2025

    We had the BEST time staying here with our sorority sisters! The property is absolutely perfect for groups — so many private bedrooms that gave everyone their own space, plus the cutest houses and cabins that made it feel like a little village just for us. The dining hall was super chill and such a great hangout spot for meals and late-night laughs.We loved how close it was to everything — food, fun activities, and plenty of outdoor space to enjoy the yard. It made planning so easy since everything we needed was right there or just minutes away.This spot was the perfect mix of comfort, charm, and convenience. We’re already talking about making this our annual getaway location. Highly recommend for any group looking for a fun, private, and memorable place to stay!

  • William F.

    Submitted Aug 28, 2025

    Stayed Aug 22, 2025

    Dirty pool , broken chairs , broken steps , no hot water pictures says 1000 words

  • Kristian M.

    Submitted Jun 20, 2025

    Stayed Jun 6, 2025

    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.

  • Chana B.

    Submitted Apr 9, 2025

    Stayed Apr 7, 2025

    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!

Your dates are Available!

Total

Includes taxes and fees
$1,046+
View details