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.

Contemporary Hudson Valley home

Our home is a 1970s architectural gem located in the convenient upstate NY town of Staatsburg. It has been thoughtfully modernized and designed to encourage maximum serenity and enjoyment of both the indoor and outdoor spaces. The floating staircase, huge picture windows, expansive deck and wooded outdoor space make this home perfect for an upstate getaway - while still being close to some of the major area attractions and towns. Our historic street also features 1700s homes and a farm/brewery.

Rhinebeck Guest House, 5 min. from town, King Bed!

Lovely Rhinebeck Guest House features large bedroom with king-size memory foam bed, large living/dining room with piano, full bath and kitchen. Lots of windows and light, plus a perfect deck for drinks overlooking the pond at sunset, or enjoying coffee/tea in the AM. Property adjoins beautiful 75-acre Burger Hill Park, all 5 minutes to Rhinebeck Village! 20 minutes to Kingston, 30 minutes to Millbrook, and 40 minutes to Hudson. Kitchen has full cooking pot/pans/knives etc. supplies

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.

Extra Large Rhinebeck Village Guest House

Large loft-like house located in historic Rhinebeck Village. An easy walk to fine and casual dining, shopping and the County fair grounds. The lower level has 2 huge rooms with large beds and living area in each. One side has a TV, stereo and vinyl collection, the other a kitchen area, dining table, couch, and wood burning stove. The loft (accessible by step-ladder) has 2 more beds. The bathroom (separate rooms for bathing and WC) is between the two lower level rooms. Truly a rare find!

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Rhinecliff on the Hudson

Welcome to our home, Rhinecliff on the Hudson. Our home located in Rhinecliff, 3-4 mins to Rhinebeck Village. Sleeps 8 total. 1st Floor: King Bedroom, Queen Bedroom 2nd Floor: Living Room and Kitchen 3rd Floor: Loft with 2 Queen Beds, Living Room, Office Amazing views of the Hudson River + steps from the train station. Home is spacious with high ceilings, incredible wood work, and outdoor deck with couch, table, chairs, and umbrella. You'll love the view and convenient location.

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.

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

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!

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.