Vacation rentals with a pool in Claverack

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

4.96 out of 5 average rating, 179 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

4.89 out of 5 average rating, 187 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

4.99 out of 5 average rating, 117 reviews

A bright, modern kitchen features white cabinetry and stainless-steel appliances, including a refrigerator and microwave. The dining area includes a small table with clear chairs and a potted plant, while natural light filters through two windows, highlighting the clean, airy design.

Guest suite in Hudson

Le Soleil Suite - Pool, Mtn Views Near Hudson

A charming one-bedroom suite in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private, independent unit next to the main house. It has a full kitchen, bathroom, electric fireplace and a private backyard with a grill, firepit and pool (June to Sept.). If we are around, we give you privacy. Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 fold-out twin upon request. Close to Hudson, hiking, skiing, Olana and Art Omi.

4.96 out of 5 average rating, 378 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 end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

4.83 out of 5 average rating, 117 reviews

Two framed art pieces featuring feathers are displayed on a weathered wood wall. Above the artwork, a mounted skull adds a rustic touch to the design. The arrangement showcases natural elements that blend seamlessly with the cottage's decor.

Cottage in Hudson

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

1 minute off Warren St - salt water pool and hot sauna respite! No expense spared reviving this Historic 18th century 80 acre estate - heated pool, cedar barrel sauna, heated bathroom floors, original wood finishes, french door patio under stain glass windows from NYC’s iconic Chelsea Hotel. You’ve found the perfect combination of transcendentalist oasis with modernity providing a most comfortable stay. Enjoy a dip, steam, rolling meadows, goat petting, cocktail by fire on your patio!

4.95 out of 5 average rating, 230 reviews

An elevated back deck is adorned with comfortable outdoor seating and overhead lights, creating an inviting space. Below, a landscaped yard features lush greenery, flower beds, and stone pathways. The scene is framed by a charming wooden fence and illuminated by warm evening light.

Townhouse in Hudson

Palazzo Hudson: Luxury Home w/Pool, Hot tub, Sauna

Welcome to Palazzo Hudson! The only private vacation home in Hudson proper with a deluxe sauna, cedar hot tub, seasonal in-ground pool, chef's kitchen, & a pool-side lounge with a fireplace & art library! A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street & the Upper Depot District.

5 out of 5 average rating, 112 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

4.99 out of 5 average rating, 168 reviews

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

5 out of 5 average rating, 109 reviews

The kitchen showcases wooden cabinetry and a central island with two bar stools. A black refrigerator and stainless steel stove are visible. Natural light filters through a window, illuminating the warm wooden flooring and countertops.

Apartment in Catskill

Little Farm Stay Catskill

Rustic first floor apartment on quiet, private horse farm. Private entry, suitable for single adult or couple. Great location at the foothills of the Catskill Mountains! 6 miles to HITS Saugerties, minutes from the village of Catskill and just a short ride to historical Woodstock. Enjoy hiking, bike trails and local shopping! Full Kitchen Bedroom: Queen, small single futon Living area: Cable TV & Foosball Table Back patio: seating, grill, hot tub and pool(seasonally) Fire pit Wi-Fi

5 out of 5 average rating, 103 reviews

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter. Columbia County STR Registration #: COP-2025-015

A spacious living area features a large sectional sofa with dark cushions, complemented by a wooden chair with patterned fabric. A modern ceiling fan hangs above, and a sleek fireplace is positioned nearby. Large windows invite natural light, providing a view of the greenery outside.

4.92 out of 5 average rating, 257 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

4.97 out of 5 average rating, 173 reviews

A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.

Home in Woodstock

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Popular amenities for Claverack rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

The glass house is presented in a serene natural setting, surrounded by tall trees. Its modern design features large glass panels that provide an unobstructed view of the lush landscape. The open lawn is neatly maintained, offering a tranquil outdoor space.

4.77 out of 5 average rating, 66 reviews

Modern Glass House

4.92 out of 5 average rating, 12 reviews

Home in Richmond

Classic New England Home, Direct trail access

4.98 out of 5 average rating, 110 reviews

Home in Woodstock

Woodstock Family Home w/ Tree House + Heated Pool

4.94 out of 5 average rating, 144 reviews

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

Home in Saugerties

Bluestone Escape - Where everyone is at home.

4.98 out of 5 average rating, 93 reviews

A spacious backyard is showcased with a wooden playset featuring a slide and swings. Adirondack chairs surround a fire pit on the lush green lawn. A shed and a dining area under a canopy are visible in the background, along with the house framed by trees.

Home in Catskill

Catskill Village Ski Hike Lake Pet Main St Pool

A charming two-story farmhouse is surrounded by lush greenery, featuring a mix of green and yellow siding. The front porch is adorned with white railings and steps, inviting guests to enjoy the tranquil setting. Gabled roofs and large windows enhance its quaint character.

4.95 out of 5 average rating, 43 reviews

Charming Upstate Escape | Fire Pit & Starry Skies

The two-story farmhouse features a white exterior with dark shingles and light-colored shutters. A welcoming front entrance is highlighted by a small porch. Lush green grass and trees surround the home, enhancing its serene setting.

4.95 out of 5 average rating, 20 reviews

Kees Cottage

4.98 out of 5 average rating, 113 reviews

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

Home in Saugerties

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Condo rentals with a pool

4.89 out of 5 average rating, 104 reviews

A cozy bedroom features rustic wooden walls with decorative hearts. A spacious bed is dressed in light linens, accompanied by a bedside lamp and a small dresser. A guitar leans against the wall, adding a touch of character to the room.

Condo in Hunter

Cozy Gem with Mountain Views

A bright living area is featured, showcasing a cozy arrangement of gray sofas around a circular coffee table. A modern ceiling fan circulates air above while large windows reveal stunning valley views, allowing natural light to fill the room. An electric fireplace adds warmth to the space.

5 out of 5 average rating, 29 reviews

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Superhost

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

4.67 out of 5 average rating, 123 reviews

Windham Condo

4.9 out of 5 average rating, 233 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

The living area features a pair of patterned armchairs and a comfortable brown sofa, positioned around a wooden coffee table. A television is mounted on the wall, and a doorway leads to a balcony. Natural light enters through large glass doors.

4.92 out of 5 average rating, 12 reviews

Luxury 3-bedroom Condo on Windham mountain

A modern kitchen area is presented, featuring stainless steel appliances, including a refrigerator and microwave. A bar counter with three dark wooden stools provides seating. Soft lighting is emitted from pendant fixtures above, illuminating the warm wood cabinetry and granite countertops.

4.92 out of 5 average rating, 62 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

A spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.

5 out of 5 average rating, 6 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.

5 out of 5 average rating, 8 reviews

Luxury Ski in Ski out Condo + Amenities

Other vacation rentals with a pool

5 out of 5 average rating, 10 reviews

A sleek black barn structure is presented, featuring a simple yet elegant design with wooden vertical slats. The large doors are framed by neatly trimmed boxwood plants on either side. Soft gravel pathways lead up to the entrance, surrounded by lush greenery under a bright blue sky.

Barn in Sharon

Black Barn

4.98 out of 5 average rating, 83 reviews

A charming white farmhouse is framed by tall trees and lush greenery. The home features dark green shutters and a covered front entrance. Surrounding gardens with blooming flowers contribute to a serene outdoor setting, making the property inviting and spacious.

Home in Germantown

Columbia County Farmhouse with Pool

4.92 out of 5 average rating, 37 reviews

The exterior of the ranch-style cottage features a spacious front porch with steps leading to a decorative door. Flower boxes adorn the windows, and a well-maintained yard with grass and landscaping surrounds the home. A gravel driveway provides access to the entrance.

Cottage in Athens

White Bunny Cottage

4.99 out of 5 average rating, 74 reviews

Home in Catskill

Catskill Mountain View Home with Hot Tub

4.99 out of 5 average rating, 89 reviews

A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.

Home in Great Barrington

Stunning luxury home with fire pit

4.96 out of 5 average rating, 53 reviews

A warm and inviting living space features wooden walls and a high ceiling lined with beams. A modern wood stove stands in the corner, alongside neatly stacked firewood. Comfortable armchairs with soft throws are arranged on a colorful area rug, enhancing the cozy ambiance.

Cabin in Athens

Lake Cabin

4.95 out of 5 average rating, 20 reviews

A two-story lake house is presented under a clear blue sky, featuring a brown wooden exterior and a spacious front yard. The driveway leads to a two-car garage, with double garage doors that add to the home's charm. Surrounding greenery enhances the peaceful setting.

Home in Athens

Mountain-view Escape