Holiday rentals with a pool in Catskill

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Family · Location · Sleep quality

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Value · Family · Walkability

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

Family · Location · Getting around

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Value · Family · Condition

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge

Experience Catskills luxury at The Swan Home, a modern retreat designed by MPM Designs LLC. Newly renovated with high-end furnishings and curated outdoor living, it offers a private escape with heated pool, hot tub, cold plunge, sauna, open-air shower, and outdoor fireplace under the stars. Just 9 minutes to Hunter Mountain and 2 hours from NYC, with access to Woodstock, Rhinebeck, and Windham. Enjoy high-speed Wi-Fi, a home theatre, and designer finishes—perfect for a refined weekend getaway.

Value · Family · Comfort

Hudson River Sunset Getaway

With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Family · Location · Hiking

Catskill Village Ski Hike Lake Pet Main St Pool

Welcome to our cozy retreat in historic Catskill village, just a block from Main Street's vibrant cafés, breweries, art galleries, and historic sites. Outdoor enthusiasts will appreciate our proximity to skiing, zip-lining, hiking, and golf. Enjoy water activities like kayaking, paddleboarding, and boating on the nearby Hudson River. We're conveniently located 10 minutes from the Hudson Amtrak station and about a 2 to 2.5-hour drive from NYC, making it an ideal getaway.

Family · Location · Quiet

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Family · Value · Hospitality

Upstate Getaway btw Rhinebeck+Hudson

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

Location · Family · Pets

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Location · Family · Nearby

Hudson Valley Lake · Hot Tub · Dock · Games · View

Welcome to my lakefront getaway nestled on the shores of picturesque Sleepy Hollow Lake! Grab the kayak and explore the lake or lounge the day away in the hot tub. ✔ Private Hot Tub, BBQ, Fire Pit ✔ Lake Access (Dock, 2 Kayaks, Paddleboard) ✔ Pool Table ✔ High-Speed Wi-Fi ✔ Community Amenities (Seasonal Pools, Sports) Perfect for families and groups looking to relax. Not suitable for parties.

Location · Family · Air conditioning

Catskills Retreat | Heated Pool & Hot Tub

Tucked away in the Catskill Mountains, our private cabin feels like you’re a world away while still being just minutes from hiking, restaurants, skiing, and charming mountain towns. It’s one of those places where mornings start with coffee surrounded by nature, afternoons are spent by the pool, and evenings end in the hot tub or around the fire pit under the stars.

Value · Location · Comfort