Family-friendly vacation rentals in Greenwood Lake

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Top-rated family-friendly rentals in Greenwood Lake

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Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 422 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Apr 12 – 19

G$26,946 GYD per night

Guest favorite

Guesthouse in Warwick

4.96 out of 5 average rating, 249 reviews

Bellvale Guest House on Solar Powered Mini-estate

Town of Warwick Short Term Rental Permit #32553 Come spend a relaxing week-end on our 4 acre mini-estate in beautiful Warwick, about one hour from NYC. Our detached 2 bedroom guest apartment is in a secluded setting, yet boasts spectacular views of the Warwick Valley. There are numerous attractions for all tastes including craft breweries and wineries. Close to home, Mt Peter Ski Area is within walking distance and further up the mountain is the nationally famous Bellvale Farms Creamery.

Mar 9 – 16

G$40,543 GYD per night

Guest favorite

Cottage in Highland Lakes

4.97 out of 5 average rating, 268 reviews

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

Jan 8 – 15

G$80,815 GYD per night

Guest favorite

Home in Greenwood Lake

4.91 out of 5 average rating, 123 reviews

Casa del Lago, Boating, Hiking & Grilling!

Welcome to GWL! This 108 year old Arts & Crafts home is charming with high ceilings & beams, trim moldings, porch and original hardwood floors. There is plenty of outdoor space including back yard, a deck, patio & lake deck. Plenty of nooks for you to relax, grill, sip wine from the enclosed porch or watch TV. House faces the lake but you must cross a low traffic street for lake / dock access. Plenty of parking driveway & lakefront. Short walk to the Village, close to all! PERMIT #18-07697

May 18 – 25

G$75,965 GYD per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Dec 13 – 20

G$23,889 GYD per night

Guest favorite

Cabin in Greenwood Lake

4.96 out of 5 average rating, 388 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Sep 21 – 28

G$46,503 GYD per night

Superhost

Cottage in Vernon Township

4.93 out of 5 average rating, 164 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Sep 3 – 10

G$38,015 GYD per night

Guest favorite

Cottage in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Aug 14 – 21

G$25,711 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 744 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 10 – 17

G$22,961 GYD per night

Guest favorite

Apartment in Chester

4.96 out of 5 average rating, 336 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Jan 11 – 18

G$33,001 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 680 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Nov 27 – Dec 4

G$27,491 GYD per night

Superhost

Cabin in Greenwood Lake

4.89 out of 5 average rating, 104 reviews

Log cabin and Greenwood Lake

Our chestnut log cabin was built in the 1930s. The views of the lake from the hot tub are great. Roast marshmallows around the fire pit on the deck or play games with the family in the main room. We are close to family friendly skiing and tubing. A great getaway only an hour from Manhattan! Please note: No more than 4 adult guests per booking, or families larger than 6.

Aug 17 – 24

G$60,294 GYD per night