Holiday rentals with a pool in Monroe

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

**Dates blocked? Send us a message. We haven't opened most of our 2026 calendar yet & many days are actually available.** 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

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Scenic River View Escape | New Paltz

Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Light-Filled Upstate Home, Perfect Location

Located just south of the Catskills in the beautiful Rondout valley, under 2 hours away from Midtown Manhattan, The House On Smith Lane was built in the modern farmhouse style. Striking the perfect balance between classic and comfortable, our home is equipped with fully modern amenities, including state-of-the-art kitchen and appliances, nest thermostat heating system, and an in-ground pool with bluestone coping (pool is open from Memorial Day to Labor Day). @thehouseonsmithlane

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Your Summer Escape - Cozy Forest with Deck & Views

Welcome to our peaceful sanctuary, tucked away in nature's embrace! This delightful home fuses modern amenities with the beauty of the wild, ideally located near a vibrant forest filled with towering trees. Outside, nature’s wonders await. Step onto the expansive deck, where cozy seating invites you to relax and take in the mesmerizing forest views. You might catch sight of birds flitting through the canopy or glimpse wildlife roaming freely in their natural habitat.

The Harvest Guest House~ Hidden Gem with Pool

Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.

Luxury Retreat with pool in historic Kingston

This historical brick building turned into a private residence on the Hudson River is your luxury retreat with top-notch amenities and finishes; perfect for a getaway weekend and longer stay. The house is 7 min walk from the marina and restaurants in the historic district of Kingston and seconds from the Hudson River. Perfect location for hiking lovers, boat lovers, and nature lovers.

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.