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.

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

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, kayaks, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

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

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.

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

Welcome to our Stunning 5-Bedroom, 4-Bathroom Modern Farmhouse with Private Pool, Hot Tub, Game Room, and Amazing Views! - Newly Renovated - Tastefully Decorated, Modern Finishings - Amazing Mountainside Panoramic Views, Lots of Sunlight - Over 2,000 SqFt of Outdoor Patio Space (BBQ, Fire Pit, Games) - 5min to I-87 & Catskill Downtown, 15min to Hudson (Amtrak), 25min to Windham (Ski/Golf), 35min to Hunter Ski Area Perfect for Vacationing, Entertaining, Group Retreats and Family Gatherings!

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!

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.

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

A Very Cozy House With a Very Big Yard

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.

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.