
Holiday rentals with a pool in Greenwood Lake
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Greenwood Lake
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without 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.

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing
A modern 3BR/2BA Catskills retreat on 6 private acres with a hot-tub, and fireplace. Perched on a hill, this single-level home offers serenity, scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Fireplace Hot Tub Spa Mini Ping-Pong Dart Board High-speed Wi-Fi Narrowsburg Offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

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

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

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.

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.

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.

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!
Location, location, location! This is a very unique, open concept unit. In lieu of a balcony, it has a huge picture window that allows breathtaking center building panoramic views of the slopes! It's also a top floor unit so extra height ceilings. That open concept continues inside where the walls were minimized leading to the master bedroom having an archway in lieu of a door. The result is a very spacious main living area perfect to gather in front of the fire.

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.

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
House rentals with a pool

TheGoshenGetawayPoolHotTubLegoLandArcade

Entire Home (private pool), Event Friendly

Scenic River View Escape | New Paltz

Private Dock/Indoor Pool/Sauna/Hot Tub - Sleeps 14

No Guest Fees, Lakefront Escape, Pets, Ski, Tubing

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Modern 5BR Pocono Cabin | Fire Pit, Hot Tub, Games
Condo rentals with a pool

Condo at Mtn Crk 1 Bdr 1 Bath sleep 4 Mtn view 234

Valley Overlook @ Mtn Creek Resort Park & Play

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

Cozy condo in Ski Resort. 2 bedroom/2 bath Unit226

Staycation Oasis! a unique Experience!

Deluxe 1 Bdr | Walkout Patio to Pool & Hot Tub! | Mountain Creek Resort @ Appalachian

Comfortable, chic, modern and sophisticated condo

âś° 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Other holiday rentals with a pool

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

Livingston Manor Retreat

Cozy Studio•Resort Stay•Mountain Creek Pool&Hiking

Chalet w/ Hot Tub, Bar & Game Room– 1 Hr from NYC!

4 bedroom house with pool (Kids & Dog Friendly)

Luxury Woodland Cabin Getaway near Warwick

Arkadia House Mid-century retreat with pool & view

Designer King 1BR Near NYC | Parking, Pool & Gym
Quick stats about holiday rentals with a pool in Greenwood Lake

Nightly prices starting at
Greenwood Lake holiday rentals start at $1,126Â NZD 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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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Grand Central Terminal
- Bronx Zoo
- Mountain Creek Resort
- Old Glory Park
- Ohel Chabad-Lubavitch
- Yankee Stadium
- United Nations Headquarters
- Chabad Lubavitch World Headquarters
- Empire State Building
- Citi Field
- Bethel Woods Center for the Arts
- Statue of Liberty
- Radio City Music Hall
- New York Public Library Main Branch
- Bushkill Falls
- Kingston-Throop Avenue Station




