Family-friendly vacation rentals in Sleepy Hollow Lake, Greene County, New York

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Top-rated family-friendly rentals in Sleepy Hollow Lake, Greene County, New York

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Guest favorite

Home in Ghent

4.87 out of 5 average rating, 271 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

Jan 27 – Feb 3

R4,281 ZAR per night

Guest favorite

Farm stay in Kinderhook

4.85 out of 5 average rating, 206 reviews

Barn House: isolated sheep farm Hudson area

April lambing season is not to be missed. A century-old brick barn, eclectic style with art everywhere, 10 miles from Hudson, near Kinderhook, now a quiet, secluded, unique residence. Gardens, sheep, and ponies are set off a country road, with a converted jungle shower, loft, and woodstove. Waterfall swimming area nearby. E-bikes are available to enjoy the nearby gorgeous Empire Trail. Easy drive to Columbia County and Berkshire spots. The farm shares space with nature as it is - country life.

Nov 10 – 17

R3,342 ZAR per night

Guest favorite

Home in Hudson

4.85 out of 5 average rating, 427 reviews

Pied-A-Terre | City of Hudson Entire Apartment

Entire Apartment in a gorgeous Queen Anne Victorian House located 2 blocks from Warren Street. Elegantly appointed with all the amenities one could need on their stay. Toasty warm. This is a sweet apartment located on the street level of my Queen Anne Victorian home. You have keyless access with your own front and back doors, access to the garden, laundry and all amenities. The apartment is cozy and full of charm and magic. * I am discouraging wedding party reservations during Covid*

Oct 19 – 26

R2,898 ZAR per night

Guest favorite

Home in Athens

4.83 out of 5 average rating, 158 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Jan 18 – 25

R2,954 ZAR per night

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 231 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Jul 19 – 26

R2,120 ZAR per night

Superhost

Home in Athens

4.78 out of 5 average rating, 222 reviews

Creative Refuge - Victorian Cottage in Athens

This guest favorite has been proud to host novelists, musicians, and their families. It is a place to recuperate, read, and reflect, on a quiet residential street, with a bucolic backyard and trees near central Athens Village, which has been described by the NY Times as "the perfect blend of old and new." Sunlit bedrooms, airy living room, equipped kitchen, and plenty of peace. There is a special energy here. You can see more at @knollhouseathens on IG. We look forward to your visit!

Jul 23 – 30

R3,117 ZAR per night

Guest favorite

Home in Hudson

4.96 out of 5 average rating, 341 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

Complete renovation with privacy. Rural mill worker's cottage is upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a rural paved road and AHET Rail Trail. Minutes to Hudson and Kinderhook. You may see Carolina Wrens, Cardinals, Chickadees, Woodpeckers, Goldfinches and Hummingbirds. The creek to the front attracts Bald and Golden Eagles, Osprey, Blue Herons, Red Tail Hawks, Ducks and Geese. ABSOLUTELY NO PETS ALLOWED.

Sep 19 – 26

R3,491 ZAR per night

Guest favorite

Cottage in Craryville

4.91 out of 5 average rating, 482 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking.

Mar 31 – Apr 7

R2,185 ZAR per night

Guest favorite

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 583 reviews

Magic Forest Farm's Mountain View Suite

Our 225 acre farm is predominantly forested, with miles of hiking trails and incredible views. Nestled in the foothills of the Catskills near Albany, we are the last home on a dead end road and have multiple secluded rentals. We are a homestead devoted to the principles of organic farming and self reliance. We grow much of our own food and forge many types of wild mushrooms. You will be sure to enjoy friendly animals around the farm and a private fenced Koi pond.

Aug 31 – Sep 7

R1,852 ZAR per night

Guest favorite

Apartment in Hudson

4.97 out of 5 average rating, 108 reviews

Spacious Retreat in the Heart of Hudson

Stay in this historic home right in the center of Hudson! This is the 2 bedroom, 2.5 bathroom owner's unit in a 3-family house, fully updated with modern amenities. Spacious living space on two stories, complete with a cozy living room, dining room table that can seat 10-12, farmhouse-style kitchen, butler's pantry, laundry room, and back porch. All within 1 block of the restaurants and shops on Warren Street, and a 12 minute walk to the Amtrak train station.

Mar 19 – 26

R8,701 ZAR per night

Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 306 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Aug 22 – 29

R8,597 ZAR per night

Guest favorite

Guest suite in Nassau

5.0 out of 5 average rating, 225 reviews

Country Two Bedroom Apartment with full breakfast

A ground floor, two bedroom apartment in host's house. Full breakfast provided. Located in New York's scenic Hudson Valley and convenient to Hudson, the Berkshires, the Catskills, Saratoga, Albany, and more. Full kitchen, separate dining room, private covered patio. Access to 23 acres of open and wooded property.

Feb 11 – 18

R2,487 ZAR per night