Vacation rentals with a pool in Greenwood Lake

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Top-rated rentals with a pool in Greenwood Lake

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 189 reviews

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

Top guest favorite
A spacious bed is centered against a soft green wall, adorned with pillows and a decorative fur throw. Two tall lamps with silver bases provide gentle lighting, while a floral artwork piece hangs above the headboard, adding a subtle touch of elegance.
Townhouse in Vernon Township
4.92 out of 5 average rating, 278 reviews

Country Chic Getaway at Black Creek Sanctuary

This Country Chic Getaway “The Angel House” is Private & Peaceful with Mountain Views. Now more than ever we need a place to escape to. “The Angel House” is located in Vernon Township at Black Creek Sanctuary, Mountain Creek's only gated community and is a quick trail walk to the slopes! Just 47 miles from Manhattan. This beautiful 2nd floor -two story/ 2 bedroom townhome offers an open floor plan w/gas fireplace,amazing views and can sleep up to 6 guests. 2 full bathrooms and a chefs kitchen.

Guest favorite
A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.
Home in Monroe
4.96 out of 5 average rating, 134 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Superhost
A spacious lounge area features a large corner couch with a mix of textures and colors. A round wooden coffee table sits centrally, surrounded by a cozy pouf and an armchair. Large windows provide natural light and views of the surrounding greenery.
Cabin in Vernon Township
4.78 out of 5 average rating, 286 reviews

Luxe 10 guest Ski Cabin Pools/Golf/Tennis/Gym/Hike

Gather your crew of 10 and escape to this stunning two-floor cabin, where adventure meets relaxation. Nestled in breathtaking scenery, this stylish retreat offers the perfect balance of comfort and outdoors. Whether you're hiking scenic trails, or simply unwinding, there's something for everyone. Enjoy year-round activities like skiing, snowboarding, mountain biking, wildlife spotting, or exploring the Appalachian Trail. This is more than a getaway it’s an experience you'll never forget!

Guest favorite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock
4.97 out of 5 average rating, 175 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Top guest favorite
A light-filled living area features a comfortable sofa and a blue armchair, complemented by a modern coffee table. Two framed images hang on the wall, with a large window providing views of the greenery outside.
Apartment in Vernon Township
4.95 out of 5 average rating, 129 reviews

Mountain Creek Appalachian Apartment Ski slope

Relax in the most convenient Condo in Appalachian Hotel with the whole family at this one bedroom apartment, peaceful place to stay. All amenities Resort just at walking distance to Mountain Creek Ski Slope!!, 1st Floor one bedroom apartment just in front of the pool , jacuzzi and sauna facilities! Ski lift Sugar quad is close to the condo’s backyard,let us pamper you with robe and slippers available for your comfy outdoor heated pool, hot tub and sauna open all year round

Guest favorite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester
4.98 out of 5 average rating, 146 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 15 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Guest favorite
A serene bedroom space features a spacious bed adorned with cozy linens and decorative throw pillows. Geometric wall carvings in dark tones create an artistic backdrop, complemented by bedside lamps providing soft lighting. Natural light fills the room through a nearby window.
Condo in Vernon Township
4.93 out of 5 average rating, 182 reviews

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Ski-In-Ski-Out ! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 118 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest favorite
A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.
Home in Kerhonkson
4.95 out of 5 average rating, 392 reviews

Fenced & Salt Water Pool | Cozy Catskills Cottage

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.

Guest favorite
Chalet in Warwick
4.93 out of 5 average rating, 136 reviews

Mountain Luxury: Pool, Theater & Outdoor Kitchen

Permit #P25-0121 Discover the perfect blend of mountain charm and luxury on several acres just minutes from Downtown Warwick. This serene retreat features stunning Hudson Valley views, a heated pool, covered outdoor kitchen with fireplace, and elegant indoor spaces including a Great Room and cinematic media room. Enjoy wineries, orchards, hiking, skiing, and more all within 15 minutes and just one hour from Manhattan.

Top guest favorite
Cottage in Eldred
4.98 out of 5 average rating, 129 reviews

Bella Cottage w/Cozy Fireplace, Winter Getaway

Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

Popular amenities for Greenwood Lake rentals with a pool

Quick stats about vacation rentals with a pool in Greenwood Lake

  • Nightly prices starting at

    Greenwood Lake vacation rentals start at ﺩ.ﺇ2,461 per night before taxes and fees

  • Verified guest reviews

    Over 90 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Greenwood Lake rentals

  • 5 Average rating

    Greenwood Lake stays are highly rated by guests—averaging 5 out of 5!

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