Holiday 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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Top guest favourite
Home in New Paltz
4.98 out of 5 average rating, 522 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. fireplace, 5 person hot tub short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village THE WHOLE PLACE IS YOURS- HOUSE, PROPERTY, POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

Top guest favourite
An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.
Home in Accord
5 out of 5 average rating, 103 reviews

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

BoHo Farm House is a luxe, modern 3BR/3BA retreat on 8 stunning acres in Accord, Hudson Valley with a large fully-fenced area for dogs & kids to roam safely. Featured in PureWow, this newly renovated Scandi farm escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. 5 minutes from Inness, Westwind, Arrowood, and the towns of Stone Ridge & Kerhonkson

Guest favourite
A tranquil outdoor pool is surrounded by colorful autumn trees, showcasing shades of yellow and orange. The three-story building, featuring a mix of warm colors, stands in the background with several balconies visible. Lounge chairs are arranged neatly around the pool area.
Apartment in Vernon Township
4.92 out of 5 average rating, 172 reviews

Lodge style getaway 50 miles from NYC patio 207

Welcome to the Appalachian! This 1 Bedroom 1 Valley View private unit sleeps 4 and is located within Mountain Creek Resort. A great spot to enjoy year round activities; Winter- true Ski-in/Ski-out hotel steps to the main lift! Summer-on site Waterpark, downhill/XC mountain biking, zip lining, horseback riding, wineries, farm stores, hiking the Appalachian trail as well as a beautiful state parks. 7 public golf courses. Fall-Pumpkin/apple picking, fresh cider donuts, beer and concert festivals!

Guest favourite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.85 out of 5 average rating, 626 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Guest favourite
A spacious bedroom features a large king bed adorned with a patterned quilt and decorative pillows. Soft lighting from a bedside lamp illuminates the area, while the en-suite bathroom is visible through an open door. Neutral tones and artwork add a touch of elegance.
Apartment in Vernon Township
4.8 out of 5 average rating, 302 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

The Appalachian is a true 4 season resort overlooking Mountain Creek Ski Resort/ Waterpark and other activities such as farms, mountain biking, multiple golf courses, horseback riding, and ziplining! NEAR LEGOLAND (25 min drive) Hike the Appalachian Trails, tour the wineries and enjoy Octoberfest/Spas/Pumpkin and Apple picking. This is a true 4 season resort with a heated(in winter) year-round OUTDOOR pool/hot tubs/Suana. Ski-in/out right to the main lift from the building

Top guest favourite
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.
Flat in Vernon Township
4.95 out of 5 average rating, 122 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

Top guest favourite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring
4.95 out of 5 average rating, 177 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Guest favourite
A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.
Flat 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 10 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 favourite
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.
Apartment in Vernon Township
4.93 out of 5 average rating, 181 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 favourite
A modern kitchenette is displayed, featuring white cabinetry and stainless-steel appliances. A comfortable brown sofa is positioned near a wooden coffee table. A dining area with a white table and chairs is also visible, alongside large windows allowing natural light into the space.
Flat in Suffern
4.92 out of 5 average rating, 154 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

Top guest favourite
A spacious living area is styled with cozy seating arrangements, including a dark sofa and a light blue patterned armchair, situated on a decorative rug. Bright natural light floods through large windows, highlighting the warm wood flooring and the open layout, including the visible stairway.
Chalet in East Stroudsburg
4.96 out of 5 average rating, 227 reviews

Near Camelback · Hot Tub · Skiing · Hiking · Games

Welcome to the Luxury Sanctuary, your serene retreat in the heart of the picturesque Pocono Mountains. Stay minutes from Camelback Mountain in a cozy house with a private hot tub and peaceful mountain surroundings. Perfect for ski trips, hiking getaways, couples, and families looking for comfort, location, and relaxation year-round.

Guest favourite
A spacious two-story house features a covered porch with white railings, providing a welcoming outdoor area. Lush green grass surrounds the property, and the backdrop includes rolling hills and a clear sky with clouds, emphasizing the serene location near the water.
Villa in Sterling Forest
4.97 out of 5 average rating, 101 reviews

Hillside villa with 9-mile lake views

Views, views and more views, this luxury getaway embraces the outdoors from every angle. Dine alfresco on the expansive deck, kick back and relax in the outdoor hot tub and spend nights with friends and family shooting pool, sitting by the fire or cooking in the gourmet kitchen. STR Permit#: 21-7747

Popular amenities for Greenwood Lake rentals with a pool

Quick stats about holiday rentals with a pool in Greenwood Lake

  • Nightly prices starting at

    Greenwood Lake holiday rentals start at £497 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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