Vacation rentals with a pool in Durham

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.

Value · Family · Heating

Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room

A spectacular six-bedroom estate offering refined luxury and comfort. Nestled within the exclusive Dingley Dell Estate, it's just a six-minute drive to Windham town and about 25 minutes from Hunter Ski Resort. The property features expansive, beautifully landscaped grounds, inviting outdoor seating areas, a prime location, and exceptional privacy. Completely renovated for ultimate guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain views.

Family · Value · Getting around

Daydream Mountain Art-Chateau | Hot Tub & Pool

Perched on a hill, with a rare Catskill Mountain view, our home is a special nature escape. Designed for relaxing, creativity, and fun. It's perfect for hiking, swimming, skiing, and exploring. A short drive to Catskill Town, Hudson, Woodstock, and other beautiful towns. Stocked with instruments, toys, books, games, a ping-pong table, and basketball. Great for families and friends. Enjoy the 50 ft. pool during the Summer or soak in the hot tub all year-round, you're in for a magical stay!

Location · Value · Hiking

Secluded Catskills Retreat w/ Hot Tub & Views

Escape to a renovated Catskills country home with modern comforts and classic charm—perfect for a relaxing getaway or outdoor adventure. Nestled in the heart of the Catskills, this retreat is just minutes from Hunter Mountain, Windham Mountain, and Kaaterskill Falls, with endless opportunities for skiing, hiking, swimming, and exploring. The home features a fenced-in yard, a stocked kitchen, and modern amenities. After a day outdoors, unwind by the firepit or soak in the hot tub.

Location · Family · Sleep quality

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 · Condition

Catskills Retreat-Pool, Hottub, Bar, Shuffleboard

Welcome to Blue Heaven! A true paradise retreat with 2 houses, your own private inground pool, outdoor shower, pool house, playground, a Speakeasy bar room with billiards, darts, and shuffleboard! Located in the heart of the Catskills just 3 minutes away from Zoom Flume water park and 15-20 minutes away from Hunter/Windham Mountains. Enjoy swimming, roasting smores in the firepit, hiking, skiing/snowboarding, snowshoeing, or soaking up the stars in our hot tub.

Family · Location · Condition

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.

Location · Family · Hot tub

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.

Family · Location · Hiking

Farmhouse • Secluded • Under 10 mins to Hudson NY

Welcome to Blue Hill Farmhouse. Circa 1857, this tastefully restored, historic farmhouse includes a separate, free standing designer guest house only minutes from Hudson, NY. Privately situated on 8 + acres featuring pasture, woods, a pond, and mountain views in the distance. The three-bedroom main house provides updated comforts like high-end appliances and central air conditioning, without compromising any of its historic charm.

Value · Location · Hospitality

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

⛰️This private modern haven is the place to be to take a break from our everyday busy lives and get away from it all. Enjoy a relaxing soak in the hot tub while indulging yourself with a glass of fine wine. The space is designed for family & friends to get together, have a good time, and enjoy each others company. Activities include hiking in the summer, skiing in the winter, barbeque and fresh air all year round!

Family · Value · Pool

Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse

A cozy townhouse 3 bdrm /2.5 bath in the center of the Catskills (Windham Mountain Village), this retreat is perfect for families, celebratory events or just a quiet nature getaway. From wineries to breweries, to zip lining and hiking, to admiring the many waterfalls, this area has something for everyone! PLEASE NOTE: POOL AND HOT TUB WILL BE CLOSED FROM SEPTEMBER 2 to NOVEMBER 27, 2025

Location · Value · Laundry

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.

Family · Value · Pool