
Vacation rentals with a pool in Greene County
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Top-rated rentals with a pool in Greene County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Mountain Views with a Cozy Fireplace In Townhome
Summer is here—Classic Townhome w/ Timeless Charm. Superhost Centrally located, spacious retreat blending clean contemporary style with classic comfort and stunning mountain views, hosted by Super host & NY native. Just a 2-min drive or 15-min walk to Hunter Mtn. Hike, bike, BBQ, and unwind or cozy up by two stone fireplaces or the outdoor fire pit. Steps from the boutique Scribner Lodge local dining. Bedrooms include A/C for summer. Perfect for a family escape or a relaxed getaway with friends.

Stunning Views • Bright 2BR • Pool • Near Farm • Lakes • Farm
A quiet mountain hideaway where the air feels soft and clean, and the view from the deck slows your whole spirit down. This cozy 2BR retreat sits between Windham and Hunter—perfect for families, solo wanderers, and anyone craving calm. Fast WiFi, a full kitchen, and short stays on selected days make it easy to escape, breathe, rest, and reconnect with yourself. Easy drive to charming little towns - Windham, Hunter , Tannersville . Swimming pool on premises , CD Lane Lake with beach and free boat

Gorgeous Mountain View | AC/Pool/Fast Wi-Fi/Hiking
Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

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!

Little Farm Stay Catskill
Rustic first floor apartment on quiet, private horse farm. Private entry, suitable for single adult or couple. Great location at the foothills of the Catskill Mountains! 6 miles to HITS Saugerties, minutes from the village of Catskill and just a short ride to historical Woodstock. Enjoy hiking, bike trails and local shopping! Full Kitchen Bedroom: Queen, small single futon Living area: Cable TV & Foosball Table Back patio: seating, grill, hot tub and pool(seasonally) Fire pit Wi-Fi

Luxury Manor Catskill | Pool, Hot Tub & Movie Room
A private six-bedroom estate offering refined comfort and luxury. Nestled within the 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 maximum guest comfort, the home also includes a pool, movie room, premium sound system, and breathtaking mountain surroundings.

Only Ski In Out on Mtn | Hike, Golf, Fish, Unwind
Slopeside 1 bedroom that fits 4! Enjoy the hiking within a 5 minute drive or just walk out onto the mountain from your porch. Access to seasonal community pool with unbelievable mountain views! Unbeatable location on Hunter Mountain, short drive to town picturesque colorful village of Tannersville, majestic Kaaterskill Falls with hiking trails, and renown fishing! Fully stocked kitchen/bathroom, full entertainment system with Netflix and all of your favorite streaming services.

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!

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.

Charming Lakefront Cabin with Hot Tub
Thoughtfully updated lakefront cabin, north of the Catskill mountains, in the Hudson Valley. Located inside the private, family-friendly Sleepy Hollow Lake community with guest access to pools, beach, tennis courts, & basketball (May-Sep). A peaceful retreat - come watch the hummingbirds from the porch or have your morning coffee looking out upon the lake! The cabin faces west over the lake so it's a wonderful spot to watch the sun set!

Catskills Farmstay: Pool, Sauna, Animals, Mt Views
Make the most of winter’s final weeks and take a break upstate. Escape the city bustle for a cozy, restorative stay at Napping Horse Farm! The Bird's Nest is a light-filled retreat nestled on 30 secluded acres at the foot of Overlook Mountain. Perfect for couples, solo travelers, and small families seeking wellness, stillness, and a memorable experience with rescue farm animals. Nature, comfort, and deep calm just 2 hours from NYC.

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!
Popular amenities for Greene County rentals with a pool
House rentals with a pool

Farmhouse • Secluded • Under 10 mins to Hudson NY

Private lakefront home, hot tub & resort amenities

Shaggerties Cozy Catskills Getaway

Birch & Buck - Stunning Views near Hudson & Hunter

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

Catskill Village Ski Hike Lake Pet Main St Pool

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

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub
Condo rentals with a pool

Cozy Gem with Mountain Views

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Windham Condo

Luxury 3-bedroom Condo on Windham mountain

4 Bedroom Condo, Close to Golf Courses and Biking

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Luxury Ski in Ski out Condo + Amenities

Entire condo in Hunter NY, Gorgeous area- sleeps 6
Other vacation rentals with a pool

Little House on the Hudson River

Excellent Comfort and Location

Modern Catskills Escape · Pool, Hot Tub, Play

Mountain View Condo • Windham

Catskill Mountain View Home with Hot Tub

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

New! Gemini House 1892 Farmhouse w/ Pool - Hudson

Modern Chalet w/Cedar SAUNA, HOT TUB & Outdoor TV!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Jiminy Peak Mountain Resort
- Howe Caverns
- Catamount Mountain Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- June Farms
- Plattekill Mountain
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Hunter Mountain Resort
- Mohonk Preserve
- Bousquet Mountain Ski Area
- Peekamoose Blue Hole
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Naumkeag
- Benmarl Winery
- Norman Rockwell Museum
- Things to do Greene County
- Nature and outdoors Greene County
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