20 Best Catskills Vacation Homes with Pools

(5 / 5)

As the hustle and bustle of daily life takes its toll, escaping to a tranquil oasis becomes an irresistible idea. Nestled within the scenic Catskill Mountains, a hidden gem of natural beauty and serenity lies a collection of vacation homes that offer the ultimate retreat. What better way to relax and rejuvenate than by indulging in the luxury of your own private pool? In this article, we invite you to dive into the world of the Catskills and discover the best vacation homes with pools that combine comfort, elegance, and stunning surroundings.

The Catskills, renowned for their captivating landscapes and charming towns, have long been a favored destination for nature lovers and adventure seekers. However, amidst the picturesque beauty lies a secret treasure trove of exquisite vacation homes with pools, inviting you to unwind and create lasting memories. Imagine waking up to the sound of birds chirping, stepping outside onto a sprawling terrace, and immersing yourself in the crystal-clear waters of a private pool. Whether you’re traveling with family, and friends, or seeking a romantic escape, these vacation homes offer the perfect blend of luxury, privacy, and awe-inspiring views of the Catskill Mountains.

These vacation homes, meticulously designed to harmonize with the surrounding natural beauty, provide an idyllic retreat for those seeking respite from the demands of everyday life. Each property boasts its own unique charm, combining modern amenities with rustic elegance. From sleek and contemporary designs to cozy and traditional cabins, there is a vacation home to suit every preference. Whether you desire an expansive poolside deck for sunbathing or a covered patio for lounging in the shade, these accommodations cater to your every need, promising an unforgettable experience in the heart of the Catskills.

Beyond the boundaries of your private pool, the Catskills beckon a wealth of outdoor activities and attractions. Hike through breathtaking trails, explore cascading waterfalls, or immerse yourself in the vibrant arts and culture scene of the nearby towns. Enjoy a round of golf on picturesque courses, embark on a fishing adventure, or simply savor the tranquility and solitude of the mountains. The best vacation homes with pools in the Catskills offer a gateway to endless exploration and adventure while providing a serene haven where you can unwind and rejuvenate in the company of loved ones.

Escape the chaos of city life and discover the unparalleled beauty of the Catskills. Immerse yourself in the luxury of private pools and picturesque surroundings, where relaxation and adventure intertwine harmoniously. Dive into Serenity: Unveiling the Best Vacation Homes with Pools in the Catskills:

Step by step method

  • 1. Fern Leaf Farmhouse

    Fern Leaf Farmhouse is a stylish country retreat nestled in the heart of the Catskills, located less than 2 hours from NYC, and minutes from the hamlet of Narrowsburg. Set down a quiet road, the house has 4 BRs and 3 BA. The house features front and back porches, a fireplace, a heated swimming pool, firepit, 2 pickleball courts and a tennis court.

  • 2. Hudson Valley Vacation Rental w/ Private Pool

    Take in unbelievable views of the Sundown Wild Forest through floor-to-ceiling windows when you stay at this 3-bedroom, 2.5-bath vacation rental. Boasting a luxurious contemporary interior and a large yard fully equipped with a private pool, hot tub, and fire pit, this home has something for travelers of all ages! Although it may be tempting to spend all day lounging in the idyllic backyard, don't forget to explore the surrounding ski resorts, trails, and wineries that Kerhonkson has to offer!

  • 3. Quiet Getaway With Mountain Views and Heated Private Pool

    Nestled on a quiet road surrounded by trees and gorgeous mountain views, this comfortable home sits on 15 acres of land offering privacy and the convenience of a 15-minute drive to Hunter Mtn resort, or Windham Mtn. 20 feet high vaulted ceilings and a 2-sided stone fireplace lend unique grandiosity to the space. The house comes with a private in-ground heated swimming pool (in season from June 2023 - Sept 2023) and an office area for any WFH needs!

  • 4. 36 ACR Waterfalls with Pool & more

    House is only about 12 minutes away from the local grocery store and the center of friendly Saugerties, with all of its marvelous restaurants, antique stores, and HITS. In just 18 minutes, you can be in the center of Woodstock for a different kind of experience. The 40' pool is heated. It is open from Memorial Day through September 16. The hot tub seats six and is available all year round.

  • 5. Secluded Catskills Retreat - Heated Pool

    This secluded house boasts all elements of water the Catskills has to offer: a heated in-ground pool, a swimming pond for sweet water lovers, a hot tub for soaking up warmth and stars any time of year. The house has 4 bedrooms that comfortably sleeps 8 guests, some exceptions made for 10 people upon request. The bright living room with views of the Catskills opens up to a deck great for out door dining and grilling.

  • 6. SECLUDED POOL, SPA & STREAM on 7 Acres

    An amazing retreat in the woods, situated on 7 beautiful acres, but still only just 5 min from downtown Woodstock. Surrounded by mature trees and gently flowing stream, you will breathe deeply and relax. GREAT for kids: in addition to the heated pool -- open in season -- we have ping-pong, a basketball net, a doll's house with furniture!


    This vacation home has a 36 ft salt water pool for summertime enjoyment and a new hot tub for year round use. The location is minutes to Ski Windham and a short drive to Hunter Mountain both great mountains to ski and snowboard.

  • 8. Beautiful Hudson Valley Woodland Retreat with Swimming Pool

    A stylish vacation rental home with 2 acres of landscaped gardens and surrounding woodland, nestled at the end of a private road. It features a new chef’s kitchen, in ground pool, deck with outdoor grill and all the modern comforts needed to enjoy your stay in beautiful Hudson Valley whatever the season.

  • 9. MODERN FARMHOUSE, near Woodstock with Deck, Fireplace, & Pool

    This beautiful home is set in the middle of 3 acres. The brand new, heated pool, 18' x 36', is finished, and is being very much enjoyed by renters. The rest of the property is wooded and private, with plenty of yard for playing and a new gas grill for cookouts. Yet for all of the seeming seclusion, the property is exactly halfway between Woodstock and Saugerties

  • 10. Hamptons on the Hudson in South Saugerties

    This vacation home has four bedrooms, 3.5 bath, Livingroom, dinning room, kitchen, and a bar area leading in to the outdoor fireplace, heated pool and hot tub. You will be a 10mins ride way from the historic village of Saugerties, Adams Farmers Market will be your go to for groceries, and for dinning you will be close to Kingston, Rhinebeck, and Woodstock.

  • 11. The Camptons House - Swimming Pool, Sauna, IceTub & HotTub

    The Camptons House is a top getaway destination in the Catskill Mountains, UpState NY. Fully renovated 4500sf house sits on one acre and has everything that you might need during your stay; year-round saltwater swimming pool, 110V HotTub, Sauna, IceTub, 7 large bedrooms, 3 bathrooms, grill hut, gym, pool table and much more.

  • 12. Located in the heart of Hunter with Pool

    Recently renovated and professionally designed, The Lodge is the perfect vacation home for families or a group of friends looking to explore everything Hunter Mountain and Windham Mountain has to offer! Pool, hot tub, sauna, fire pit, grill, Cozy Earth linens, and more ++

  • 13. Upstate Getaway with Heated Saline Pool; Kid Friendly, Perfect Location

    Have fun at this stylish place sitting on 4 acres of private, wooded property that is beautifully landscaped with a heated/saltwater pool, small pond, fire pit, outdoor dining, and grill. This home is well stocked with everything you need to stay in and relax. It’s also close to many cute towns with fine dining restaurants, wine bars, farmers markets, orchards, skiing, hiking etc. There is even a local farm stand right on the corner of the street!

  • 14. Amazing Contemporary Family Home with Pool next to Nature Preserve

    private 24 acres abutting a nature sanctuary that is only 5 minutes to the bustling town of Catskill, NY. Our home has four comfortable bedrooms with four baths. Whether you want to celebrate your family reunion, relax with your kids or gather with friends, you will love the heated pool, walks through the fields, and basketball and pickle ball court in the front driveway.

  • 15. Luxurious, Private Mtn Estate- Close to Woodstock on 15 acres w Pool and Hot Tub

    Nestled in woodlands between Woodstock and Saugerties on fifteen private acres in Upstate New York, with stunning views of Overlook mountain overlooking your very own pond. Gorgeous blue stone walls wrap around the pool deck and complement the lit in-ground pool. In ground spa pool installed on the pool deck for year-round enjoyment.

  • 16. Stylish, modern barn with chef’s kitchen, heated pool, privacy

    This one-of-a-kind converted barn is conveniently located between Woodstock and Phoenicia, 2 hours north of NYC. With four bedrooms and three full bathrooms the house sleeps up to 6 people and is ideally suited for families, with a maximum of two couples (plus kids).Dine al fresco on the deck or in the spacious screened-in porch. Relax on a poolside lounger surrounded by manicured gardens. Take a dip in the heated pool.

  • 17. High Above It All In Woodstock

    Beautiful and welcoming home, perched high above the Ashokan Reservoir, is spacious, well appointed, sun filled, and all new. The property offers stunning 180 degree views of the southern Catskills Mountains and of the Mohonk Mountain preserve. Besides the view, the property offers a luxurious in ground pool, fenced-in, one acre yard, another acre of lawn and gardens to the side of the house.

  • 18. Birch & Buck - Stunning Views near Hudson & Hunter

    Birch & Buck is a stunning escape in the heart of the Catskills, located 2.5 hours from NYC. Set on 13 private acres with unmatched views of the Catskills, surrounded by woodlands, the lodge has 4 bedrooms and 4 en-suite luxe baths. Amenities include a heated swimming pool, wood burning stove, firepit, and access to the best hiking and dining in the region.

  • 19. Romantic Luxury Chalet with Private Pool

    This rustic, warmly appointed, 625 square foot second story chalet features 18’ cathedral ceilings, a magnificent stone fireplace with realistic electric element, wide plank floors, a private balcony overlooking the private pool... and a super comfy four-poster queen size bed to ensure your restful weekend in the country. Also included are high speed Internet, 200-channel satellite TV and a robust iPod-compatible Bose stereo system.

  • 20. The Summer Situation

    The Pool House Cottage is a country cottage nestled within beautiful gardens, surrounded by woods and wildlife yet only 10 minutes from the heart of avand-garde Woodstock or the trendy vibe of the Kingston area. Enjoy your morning coffee outside in the hot tub or inside in front of the crackling propane fireplace.


Lost Password