Family-friendly holiday rentals in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Rhinebeck Ridge - A Woodland Studio Retreat

Nature surrounds this tranquil space nestled within a heavily wooded scenic ridge district, far off the road. Near Omega, Rhinebeck Village, Bard, Walkway over the Hudson, hiking, parks, wineries, swimming, antique stores, farmers markets. Newly constructed & lovingly designed by its builder owner, great attention has been given to quality details designed to soothe your soul. Ideal for singles or couples of any orientation wishing to elegantly commune with nature with all the comforts of home.

Blue Cottage in Rhinebeck

* private and quit with few minutes walk to a lake ( unfortunately not for swimming). * walking trails around the property. * 5 minutes drive to the Dutchess County fairground. * 5 minutes drive to Kingston-Rhinecliff bridge. * Seven minutes drive to the village of Rhinebeck. * twenty to twenty five minutes drive to Woodstock * Twenty minutes drive to the Omega institute. * twenty to twenty five minutes drive to the Culinary Institute of America. * ten minutes drive to Bard College.

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Acorn Hill Cottage -A mid century farmhouse gem

No list of chores. Just relax! Now accepting dogs on a case by case basis. Must inquire PRIOR TO BOOKING. Minutes to historic Rhinebeck Village, this quaint abode makes for the perfect romantic or mind clearing get away. Located directly off Route 9 tucked in the trees. Enjoy our completely separate art filled cottage. The open 550sq/ft studio floor plan will cheerfully accommodate couples & close friends. 4 persons MAX. Best suited for adult guests as the space is not child proofed.

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

15% off, fireplace, workcation spot, private pond

"Pictures understate this well-appointed home. The beds were so comfortable and the pond is so tranquil!" -Kate, May '24 Newly renovated, perfect for groups of friends, couples, and families. Large (1,700+ sq. feet), quiet, 3-bedroom home 4 min to the Village and a 7-min Uber to Rhinecliff train station (2h to Penn Station). Close to hiking, skiing, grocery stores, shops and restaurants. Back yard features a tear-drop pond, BBQ, firepit, and large dining area.

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Hibiscus Suite - Priv. Studio - Rhinebeck Village

This modern studio apartment is ideal for a weekend retreat or remote working base. Just 17 minutes from Omega, we offer a Queen-size bed, free WiFi, and a Smart TV. The fully-equipped kitchenette and work/eating bar make meal prep and productivity easy. The bathroom features a rain shower head and Bluetooth speaker. With its own entrance and ample street parking, it ensures privacy and convenience. Give it a try – you won’t be disappointed!