38 Rhinebeck Holiday Rentals

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Compare Rhinebeck holiday rentals from 7 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $44 to $4950 a night.

Information about Rhinebeck

About Rhinebeck

Welcome to this Dutchess County beauty, a historic little town nestled in the Northern New York Hudson Valley region that boasts majestic views of the Catskill Mountains and the Hudson River—it also has just the right dose of city sophistication to make for any nice weekend getaway! This one’s definitely a four-corner town that takes pride in its Dutch History. All around, subtle influences of earlier times can be seen in the array of Victorian, Greek Revival, and colonial architectural treasures scattered throughout the Village, including an early Dutch-style post office, which is one of more than a dozen sites listed on the National Register of Historic Places.

Nearby, however, it’s easy to find up-to-the-minute unique specialty shops, restaurants, and theaters that continue to bring new life onto the old tree-lined streets. Rhinebeck has also been touted as one of America’s best Gourmet towns. So with numerous fine dining options and a thriving locavore movement, foodies of all sorts will be living the dream in a quieter East Coast space that’s also super accessible to New York City, rural upstate New York, the Berkshires, and even Connecticut.

Things to Do in Rhinebeck

There’s tons to check out in and around town. Why not take a peek at automobiles and motorcycles from the golden era of aviation, or watch an air show of sky-high twists at the Old Rhinebeck Aerodrome? Kiddies will love watching those planes swoop around in circles—they’ll also likely adore checking out Wilderstein, an immense Queen Anne style country house-turned-museum that’s surrounded by numerous walking trails. Adults will also like the wholly historic site for its photo-ops and stellar views! In the summertime, there’s also the annual Dutchess County Fair, an extravaganza of fried dough and rides, or Bard College's SummerScape series, which offers a fantastic mix of opera, dance, theater, and film. For even more culture, head towards Upstate Films Theater, a cultural hub for everything about film that shows documentaries, independent films, classics, and animation. There's also a sister cinema in Woodstock, as well as a large red barn about three miles east of the Village center that houses the always-busy Center for Performing Arts at Rhinebeck. The ongoing series of Saturday children's shows are especially popular.

With all that hiking, bicycling, horseback riding, and mansion viewing, it’s safe to say that the best activity in Rhinebeck by far is still eating. The proximity of the Culinary Institute of America, in Hyde Park, to the area has provided Rhinebeck with first-class chefs and many restaurants, such as the Ironwood Grille at the Dinsmore Golf Course. What’s more is that antique lovers will discover heaven on earth by scouring the over thirty antiques dealers at the Beekman Arms Antique Market. There’s also the bi-annual Rhinebeck Antiques Fair, which showcases more than a couple hundred dealers in four large exhibition halls, the Blue Cashew Kitchen Pharmacy, a high-end specialty kitchen boutique that’s been lauded by most cookbooks, and Hummingbird Jewelers, a local store offering one-of-a-kind creations by local and international artisans. Those wanting to get a taste of the wild side can even rent a mountain bike from Rhinebeck Bicycle Shop to ride north to the heavily wooded River Road, or to pedal on out to the Montgomery Place Orchards Farm Stand, a mecca for purchasing fresh produce. Kayakers can also venture through the tall reeds and purple loosestrife of the nearby Tivoli Bays. Book a sunset tour and admire dusk from the river!

Rhinebeck Day Trips

Tourism plays a vital role in the town of Rhinebeck as well as in the surrounding areas. There are a variety of historic sites all across the region, plenty of wine tours through the Millbrook Vineyards, and plenty of food adventures to satisfy any hungry belly courtesy of the Culinary Institute of America. Naturalists will love enjoying a stroll through the Innisfree Gardens, where a 150-acre public garden featuring a 40-acre glacial lake sits, while spiritualists often head over to the Omega Institute, a 195-acre educational retreat, holistic wellness center, and spa near Rhinebeck Village that is the perfect spot to relax and unwind at.

The countryside setting of the Hudson Valley region is no doubt a visual and culinary experience like no other, with winding trails, grassy horse pastures, and vibrant fruit-filled orchards all around. In wintertime, families can also check out Burger Hill Park for the ultimate sleigh riding adventure.

Rhinebeck Accommodations

Nestled comfortably in the beautiful Hudson Valley, Rhinebeck is a true retreat where city folk of all sorts can relax in everything from historic inns and mansions, to spiritual retreats and camps. Whether you’re staying in Rhinebeck for a night, a weekend, or all season long, you’ll find rest at the various small but truly special establishments in town such as the centrally located Beekman Arms and Delamatter Inn, America's oldest operating inn. For those wanting even more sophistication, try Rhinecliff Hotel, a beautifully restored boutique hotel that’s set in a quaint hamlet overlooking the Hudson River.

There’s also the Olde Rhinebeck Inn, a beautifully preserved circa-1745 inn offering country decor that mixes rustic pieces with finer furnishings, or the Whistlewood Farm Bed and Breakfast, which provides refined, contemporary-country guest rooms along with hearty pancake or egg dishes to fuel up on before exploring one of the many trails on the grounds.

Rhinebeck Transportation

Go all out country in Rhinebeck by ditching that car! Try pedaling or paddling through this pastoral Dutchess County town, or simply by venturing in via the town’s personal Amtrak station. The train runs from Penn Station to Rhinecliff-Kingston in Rhinebeck, and once you arrive, cabs can easily be called to get around.

If you really cannot pull away from that steering wheel however, there are several driving route options to choose from, with the most-direct route being the Taconic State Parkway—it’s a couple hour drive from Manhattan. Another alternative would be traveling Interstate 87 North through New Jersey, which offers a way more scenic ride. Flyers can enter in through Stewart International Airport or Albany International Airport. Get going!

Vacation Rentals in Rhinebeck

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Rhinebeck offers 250 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $402 a night, or a long-term rental for an average price of $25 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 218 of Rhinebeck’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 75 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 175 cozy homes.

Traveling with pets? Choose from 101 pet-friendly rentals in Rhinebeck for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 7 rental sites in Rhinebeck where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 160 HomeAway rentals, 47 TripAdvisor short term rentals and 22 Booking.com vacation rentals.