Vacation rentals in Rhinebeck

4.96 out of 5 average rating, 362 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

4.99 out of 5 average rating, 203 reviews

A well-equipped kitchenette showcases wooden cabinetry with a dark countertop. A microwave and refrigerator are visible alongside a sink. A small tray holds beverages, with water bottles arranged nearby. A blue door and decorative wall piece add to the inviting ambiance.

Apartment in Rhinebeck

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.

4.99 out of 5 average rating, 523 reviews

A charming cottage is framed by trees and illuminated by warm outdoor lights. A winding path with steps leads up to the entrance, showcasing cozy decorations and inviting ambiance as dusk settles over the landscape.

Cabin in Rhinebeck

Acorn Hill Cottage -A mid century farmhouse gem

No list of chores. Just relax! We are 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.

4.91 out of 5 average rating, 468 reviews

A welcoming entrance pathway leads to a single-story home framed by lush greenery. The house features a front porch with white railings and accents, while a bright red door adds a pop of color. The surrounding lawn is well-kept and inviting.

Guest suite in Rhinebeck

Contemporary Rhinebeck Private Village Retreat

Quarters covid sanitized.Huge bedroom,CalKing bed.(twin bed avail.upon request,$30/day xtra for 2 people,$55 for 3 people w/extra bed)bathroom,(NO Kitchen)has coffeemaker, fridge,TV,Wifi,A/C, private patio & garden. No pets.PLEASE NOTE:Pic shows front of house so guests can find it,quarters on lower level to private entrance,*See Pics.Close to hiking, shops,26 restaurants,Omega, Bard College, Dutchess Fairgrounds *babies ok. No toddlers or kids under 7. June/July,Aug/Oct-wknds 2 day minimum

4.99 out of 5 average rating, 158 reviews

An open-concept space features wooden beams and large windows, filling the area with natural light. A dining table with six chairs is positioned centrally. A cozy seating area includes a sofa and armchair, while a staircase leads to the loft bedroom above.

Cottage in Rhinebeck

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.

4.98 out of 5 average rating, 128 reviews

The exterior of the house features a curved metal roof and large glass doors, allowing natural light to fill the interior. The surrounding area includes vibrant greenery and well-maintained landscaping, with a wooden deck extending in front, providing an inviting outdoor space.

Cottage in Rhinebeck

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!

4.93 out of 5 average rating, 164 reviews

The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.

Cottage in Rhinebeck

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.

Superhost

A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.

Cabin in Rhinebeck

4.88 out of 5 average rating, 388 reviews

Sunset Bungalow-Mt views on 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, and comfortable bedroom- learn more at cascadafarm.com

An airy room is highlighted by wooden beams and large windows that overlook greenery. A spacious bed with a patterned duvet is positioned beside a cozy bed. A round table and chairs are situated in one corner, complemented by a woven rug and a decorative basket.

4.96 out of 5 average rating, 183 reviews

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.

4.92 out of 5 average rating, 133 reviews

A spacious studio apartment is highlighted by a large bed adorned with neutral bedding and vibrant throw pillows. A kitchenette with red accents is visible in the background, featuring modern appliances. A work bar with high chairs offers additional seating, while warm wood flooring complements the overall decor.

Apartment in Rhinebeck

Private Studio Close to Downtown Rhinebeck

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!

The exterior of Long Pond Cottage is featured, showcasing a charming Victorian design surrounded by lush greenery. A welcoming porch with seating invites relaxation, while vibrant flowers add a touch of color to the landscape. The tranquil setting is enhanced by the surrounding trees.

4.98 out of 5 average rating, 164 reviews

Long Pond Cottage, Country Retreat in Rhinebeck

Nestled down a quiet, country road, you’ll find this charming, idyllic retreat. Less than 15 minutes from the village of Rhinebeck, Long Pond Cottage captures the best of the Hudson Valley. This two bedroom, one bathroom Victorian sits on just under an acre of land, offering ample outdoor space to enjoy the warmer months, and is the perfect cozy spot when the weather turns colder. Self check-in at 4pm and check-out 11am. Pet friendly.

A spacious outdoor area is highlighted by a circular pool surrounded by a sun deck and lounge chairs. Adjacent, a covered bar area is visible near flowering plants. Lush greenery and trees frame the property, enhancing the tranquil setting.

4.95 out of 5 average rating, 192 reviews

On The Hill in Rhinebeck

Perched on a hill, this 1930’s cape with a facelift sits just over a mile from the center of Rhinebeck. The first floor is open between the kitchen, dining area and living room. Two private bedrooms and one full bath are also on the first floor. The master suite is up on the second floor with a huge master bathroom featuring a jacuzzi and glass shower. On the hill you’ll experience tree top views and a wonderful countryside experience.

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Popular amenities for Rhinebeck vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Pet-friendly vacation rentals in Rhinebeck

4.93 out of 5 average rating, 162 reviews

A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

Home in Saugerties

Upstate Waterfront Saugerties Retreat-Near HITS

Surrounded by vibrant autumn foliage, a house is nestled among colorful trees. A pathway leads to the entrance, while a cozy fire pit and chairs are positioned in the lawn, creating an inviting outdoor space for relaxation.

4.92 out of 5 average rating, 242 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

4.85 out of 5 average rating, 182 reviews

The exterior of a rustic cottage is presented, featuring large windows that allow natural light to fill the interior. A wooden deck leads to a glass-paned door, framed by light-colored siding and contrasting trim. Trees and greenery are visible in the background.

Apartment in Salt Point

Arcady - Modern, 1br cottage

4.98 out of 5 average rating, 322 reviews

A modern tiny house is framed by lush greenery, featuring a wooden exterior and large windows that invite natural light. A spacious deck with a full-size dining table is visible, surrounded by a well-maintained landscape of plants and grass.

Tiny home in Saugerties

Modern Catskills Cabin

4.94 out of 5 average rating, 348 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

4.97 out of 5 average rating, 346 reviews

Home in Germantown

Private Cottage/Mountain Views/Trails/Fire pit

4.99 out of 5 average rating, 334 reviews

A cozy bedroom features a spacious bed with a textured brown throw, complemented by a plush area rug. A gas fireplace is framed by wooden shelving, while large windows with blue shutters allow natural light to illuminate the room.

Home in Germantown

Private Hudson Valley Loft on 200 Acre Horse Farm

4.92 out of 5 average rating, 186 reviews

A bright living area features a cozy seating arrangement with light-colored furniture and wooden accents. Shelves display various decorative items, while a large window allows natural light to fill the space. The entrance showcases a beautifully carved door and soft greenery adds a touch of nature.

Home in Woodstock

Serene Retreat w/ Cedar Hot Tub & Fire Pit

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Other great vacation rentals in Rhinebeck

4.94 out of 5 average rating, 261 reviews

A light-filled living space features rustic white walls and wooden floors. A cozy soapstone stove stands beside a small seating area with a wicker chair and a couch. The doorway leads to a wooden-paneled area with hanging coats and boots, inviting a sense of home.

Guesthouse in Tivoli

Light-filled guest cottage

The historic colonial farmhouse is flanked by lush greenery and flowering plants. A stone pathway leads to the inviting covered porch, where deep green columns support the upper deck. The metal roof glistens under the bright blue sky scattered with fluffy clouds, creating a peaceful country scene.

5 out of 5 average rating, 16 reviews

All-Season Rhinebeck Modernized Colonial Retreat

5 out of 5 average rating, 38 reviews

The exterior of a charming post and beam barn is showcased, featuring a wooden facade and large windows that allow natural light to illuminate the interior. The entrance includes a double door with a decorative x-design, set amidst a tranquil wooded landscape.

Barn in Rhinebeck

Applebarn

4.99 out of 5 average rating, 95 reviews

The exterior of the guest house displays a blue wooden façade with multiple windows. A wooden deck, equipped with a couple of white chairs, extends from the house. Surrounding greenery and a grassy area complement the inviting outdoor space.

Guesthouse in Rhinebeck

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

A light-filled living area features a comfortable gray sofa adorned with yellow and white pillows. A clear coffee table is positioned on a patterned area rug. A side chair and lamp provide additional seating, with large windows framing views of the surrounding greenery.

4.93 out of 5 average rating, 60 reviews

Rhinebeck Blue Door Cottage

5 out of 5 average rating, 54 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

4.99 out of 5 average rating, 137 reviews

A cozy sleeping area is presented with a spacious bed adorned with soft linens and decorative pillows. A warm lamp on a bedside table provides gentle illumination, while natural light filters through a nearby window, offering a view of the wooded surroundings.

Cabin in Saugerties

Sweet Saugerties A-Frame - 10 mins from Woodstock