Holiday rentals with a pool in Monticello

Bella Cottage w/Pool, BBQ - Catskill Getaway

** Pool opens May 8 weekend! It is an above ground heated pool, the temp preset to 84 Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Cozy Cottage w/ Pool+Jacuzzi+Sauna+ Reading nook!

This lovely cottage sitting on almost 3 acres of wooded land is nestled perfectly in the gateway to the Catskills region. It’s a wonderful getaway from the city to recharge, relax and enjoy the nature that is readily available. The pool, hot tub and the newly installed sauna are the perfect setting to enjoy the serenity of a relaxing day or evening. You can enjoy cooking, reading in our cozy reading nook, bbqing, hiking or many other activities that the Catskills region is famously known for.

Experience The Zen House

Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

Hike & Sauna! Modern Mountain Escape

Welcome to a brand-new custom-built A-frame nestled in the heart of the Catskills. Set in the slopes of Pakatakan Mountain and surrounded by protected forest. Inspired by traditional A-frame designs, every detail has been carefully considered. From the curated home away from home experience to the high-end finishes and modern amenities. Enjoy a wraparound deck overlooking the forest, beautiful stone landscaping, a fire pit, outdoor grill, and plenty of space to relax and unwind outdoors.

Luxury Retreat: Indoor hot tub, Glow Mini Golf.

Book now and experience the magic of Lux Cabaña, a retreat designed for unforgettable group getaways in the Mt. Pocono mountains. Indoors enjoy a cozy fireplace living room, chef-ready kitchen, stylish bedrooms, indoor sauna + hot tub, game room, and gym. Outdoors glow-in-the-dark mini golf, outdoor movie theater under the stars, outdoor Sauna and a fire-pie. Minutes from skiing, hiking trails, lakes and city attractions. Perfect for family gatherings, birthdays and friends’ weekends.

15 mins from skiing - secluded cabin with hot tub

This 3 acre hidden gem is tucked away in the woods of the Catskills. It's a wonderful getaway from the city or any bustling lifestyle. The outdoor fire pit and hot tub are both the perfect settings for serenity. When you come up here you can enjoy hiking, leaf peeping, cooking, swimming or simply lounging & listening to our record collection and watching nature exist around you. Our house is about 20 minutes from Big Bear mountain which is a great (small) mountain for skiing and tubing.

Summer Secluded Getaway + Hot Tub+Swim Hole+Trails

🏡 Luxury 3,200 sq.ft Log Cabin on 15 Private Acres 🛏️ 4 Bedrooms + 3 Bathrooms | Perfect for families & groups 🌲 Secluded forest retreat with breathtaking Delaware River views 👙 7-seat hot tub open year-round and professionally maintained 🏞️ Private hiking trails, waterfall + creek + natural swim hole 🔥 Outdoor fire pit + indoor wood-burning fireplace 🐾 Pet friendly (up to 2 low-shedding pets allowed) 📺 Smart TVs, cable service & strong Wi-Fi

Spacious Catskills Farmhouse on over 5 acres!

Spring into fun in the Catskill Mountains! Our outdoor pool will open Memorial Day weekend! Enjoy a hike at one of our local trails or nature preserves. Try your luck at the casino, spend a day at the indoor water park, or play a round of golf at one of the local courses. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.

Condé Nast featured A-frame. Hot Tub. Lake. Pools

Sink into the hot tub and let the Poconos do the rest. This Condé Nast-featured mid-century A-frame is nestled among the trees, just minutes from the lake — a beautifully curated escape two hours from NYC with everything you need to completely unwind. Soaker tub with a tree-top view, chef’s kitchen, fire pit, community pools, and a bathroom so good it’s been featured in Condé Nast, Houzz and West Elm. This is the one you’ve been saving on Pinterest

Design Scandi Retreat, Heated Pool, Dogs Welcome

BoHo Farm House is a luxe, stylish 3BR/3BA retreat on 8 scenic acres in Accord, Hudson Valley—with a fully fenced area for dogs to roam safely. Featured in PureWow, this Scandi-style escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. Dog-friendly luxury meets fall and winter serenity!

6-Acre Narrowsburg Estate: Private Pool, Hot-Tub

A modern 3BR/2BA Catskills retreat on 6 acres with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's Town Center with shops and restaurants, this house is perched on a hill, offering serenity and scenic views. Enjoy modern decor, premium bedding, AC, and fast Wi-Fi. Pool season for 2026: May 22nd - Sept 14th. Hot tub is always open.