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.

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

A modern oasis in the Hudson Valley near hiking, skiing, apple-picking, antiquing, and other fun seasonal activities only 1.5 hours from NYC. Enjoy swimming in a heated pool? Great! We have a beautiful pool (Opens 4/1) and pool house complete with an outdoor bar and hot tub. Lovely outdoor garden with a fire pit nestled in the middle. A patio with a gas grill and pizza oven is ready for all chefs. We feature a three-person sauna inside! Just secluded enough to be perfect for larger gatherings!

midcentury mod * POOL * walk out trail 2 mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 -Sept 30 HOT TUB YEAR ROUND

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!

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

Mid Century Mod 5-Bed, Pool OPEN!, Dogs Welcome

Experience the ultimate family vacation in this exquisite Kerhonkson retreat. This five-bedroom, three-bathroom home offers a blend of mid-century modern design and luxurious amenities. Enjoy a private, heated saltwater pool, a chef's kitchen, and a double-sided fireplace. The fully fenced backyard ensures a safe and enjoyable space for children and pets. Explore the beauty of the surrounding area and create lasting memories.

Hike & Sauna! Modern Mountain Escape

Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.

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.

Catskills Modernist Cabin Pool Hot Tub

Escape to a designer Catskills retreat 2 hours from NYC. This secluded mountain home on 10 private acres sleeps 10 and offers 360-degree views. Features a private heated pool, hot tub, and stylish modern interior with a wood-burning stove. Perfect for families and groups seeking a serene getaway with luxury amenities, surrounded by nature.