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!

Design Scandi Retreat, Heated Pool, Dogs Welcome

Escape to BoHo Farm House, a Japandi-inspired retreat on 8 private acres in Accord, in the Hudson Valley. Spend sunny afternoons beside the pool, grill local finds, and stargaze around the firepit. The screened porch offers the perfect setting for relaxed meals on warm days next to nature. Stroll the property and pick fresh seasonal herbs and veggies from the garden. Featured in PureWow's list of pet-friendly escapes near NYC, BoHo Farm House was designed for effortless year-round living.

Secluded Cool Summer Cabin with mini pool

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.

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

Fenced & Salt Water Pool | Cozy Catskills Cottage

The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

Private Dock/Indoor Pool/Sauna/Hot Tub - Sleeps 14

Luxurious Lakefront home with a private dock, indoor heated pool, sauna, hot tub, game room, and so much more. Ideal for large groups, it sleeps 14 people and has 3 King beds, 1 Queen, 2 Full and 4 Twins. ✓Lakefront home w/ Private dock ✓Indoor heated pool & Sauna ✓Wood-burning fireplace (living room) ✓Covered hot tub ✓Game Room ✓Driveway for 6 cars ✓Playground ✓BBQ ✓Free coffee ✓Washer/Dryer ✓Private dock (summer's only)

Au Bon Orchard - Hot Tub - 56 Private Acres

Au Bon Orchard is nestled between some of the Catskills most popular destinations like Roscoe, Liberty and Livingston Manor; you will find Au Bon Orchard. - 2 Hours from NYC - Infiniti Pool (May, Post Memorial Day - Mid September) - Hot Tub - EV Car Charger - 56 Private Acres - Private Waterfall - Catskill Mountain Views - Close to: Neon Croissant, The Smoke Joint, Livingston Manor, Liberty - 3 Beds 2 Bath

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

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.