Vacation rentals with a pool in Monticello

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

This cape cod style cottage is situated at the end of a gravel strewn driveway lined on both sides by giant pine trees offering shade and privacy from the road. We love how the backyard opens directly to a small forest that you can explore and hike around in as well as the proximity to shops, restaurants, hiking, and kayaking in the Delaware River. Don’t be surprised to hear a woodpecker or two as you enjoy your morning coffee or a deer or two to stop by on a lazy afternoon barbecuing and hanging out in the pergola. The new jacuzzi offers the ideal spa experience while enjoying all of what nature has to offer. Sitting around the fire pit is the perfect activity to enjoy under the twinkling night sky and solar powered string lights

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.

9BR Log Cabin Home w/ Hot Tub & Swimmable Pond

~Completely renovated and newly furnished~ Enjoy this spacious 9 bedroom log cabin home for large gatherings on 30 acres w/ a swimmable 1 acre private pond and a new hot tub. Perfect for multiple families and large groups with a total of 23 beds! No frat parties or other excessive parties allowed. There are multiple places to gather- The main floor open concept living room, the second living room on the main floor, the basement lounge area, the arcade, and wrap around porches with seating.

Enchanted Forest Escape | Hot Tub | Movie Screen

A truly unique stay in the Pocono Mountains, home to rolling mountain terrain, breathtakingly beautiful waterfalls, thriving woodlands, + 170 miles of winding river. Created with the “ultimate night in" themed experience, guests can sip wine under the stars in a private hot tub, + enjoy movies on their own 135" movie screen equipped w/ the world's first LED 4K gaming projector. Enjoy themed bedrooms and experience a stay where the forest takes you away as you stay in ultimate comfort + luxury.

3BR/2BA • Private Pool & Hot Tub Near Bethel Woods

A modern 3BR/2BA Catskills retreat with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's shops and restaurants as well as Delaware River access for swimming and hiking. 15 mins to Bethel Concerts. Perched on a hill, offering scenic views and serenity- a true getaway destination. Enjoy modern decor, premium bedding, AC, fast Wi-Fi, and purest water that you’ll find. Swim, grill, play ping-pong, darts, star gaze. Pool season ends 9/14th. Hot tub is always open.

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!

Dog friendly, heated pool & Hot Tub w/ fenced yard

Escape to a modern mini barn 7 mins from Narrowsburg with a heated pool, hot tub, fire pit, high-speed Wi-Fi, Ev charger, backup generator and a fully fenced yard for your pups! Set in the gorgeous Hamlet town of Narrowsburg, my home is a 5 min drive into Narrowsburg Main Street! Bethel, Callicoon, Barryville, Livingston manor, are all 25 mins away. If you're looking to ski Big BEAR Mountain is close by! High speed internet 500mps. 7 day bookings and monthly bookings receive discounts!

Secret Getaway Nestled in a Woodland Setting

Welcome to our Pocono Mountain escape!! Perfect for families, couples & friends! Less than 1 mile from pools, restaurant, tiki bar & skiing!! Our cozy home provides surroundings of nature while staying close to fun. Located in Masthopes' amenity filled four-season community - Lake and beach access just a short drive!! If it's a need to disconnect & recharge or if you are seeking adventure here in the beautiful Poconos, let our happy spot be your home away from home too! :)

Luxe modern A Frame, Hot tub and new heated pool

Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

Livingston Manor Pool and Lake Retreat

🛎️ Bookings require an Airbnb account with previous host reviews. Thanks for understanding! Escape to our stylish modern chalet in the heart of Livingston Manor — a Catskills favorite! Relax in your private pool, unwind by the wood-burning fireplace, and recharge in the cozy zen loft. The home also features a pool table and three comfortable bedrooms, making it the perfect retreat for families or friends.

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.