Holiday 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, 172 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!

4.88 out of 5 average rating, 172 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, 113 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 - Fire pit, Views 10 Min To 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, 375 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.

4.83 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!

4.85 out of 5 average rating, 185 reviews

A bright and modern kitchen features white cabinetry and a stylish backsplash. An island with four wooden stools provides seating. Appliances include a refrigerator, dishwasher, and coffee maker, while natural light fills the space from overhead lighting and large windows.

Townhouse in Hunter

Gorgeous Mountain View | Ski/Fast Wi-Fi/Wood Stove

Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

4.95 out of 5 average rating, 137 reviews

A well-equipped kitchen features a central island with a spacious countertop. Modern appliances, including a stove, oven, and sink, are visible, along with ample storage cabinets. Large windows allow natural light to fill the space while providing views of the pool and surrounding landscape.

Home in Germantown

Hilltop modern with stunning mountain views

Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

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, 255 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

5 out of 5 average rating, 107 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.

Flat 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, double futon Living area: Cable TV & Foosball Table Back patio: seating, grill, hot tub and pool(seasonally) Fire pit Wi-Fi

4.98 out of 5 average rating, 103 reviews

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

5 out of 5 average rating, 100 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.

4.95 out of 5 average rating, 114 reviews

The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.

Cabin in Athens

Charming Lakefront Cabin with Hot Tub

Thoughtfully updated lakefront cabin, north of the Catskill mountains, in the Hudson Valley. Located inside the private, family-friendly Sleepy Hollow Lake community with guest access to pools, beach, tennis courts, & basketball (May-Sep). A peaceful retreat - come watch the hummingbirds from the porch or have your morning coffee looking out upon the lake! The cabin faces west over the lake so it's a wonderful spot to watch the sun set!

Popular amenities for Claverack rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 48 reviews

A bright living room showcases a comfortable gray sofa with colorful striped pillows, complemented by two green armchairs. A wooden coffee table with a striped blanket is centered on a vibrant area rug. Natural light filters through patterned window treatments, highlighting the wooden beams and stylish decor.

Home in Pine Plains

Stunningly Designed Luxury Home w/ Pool & Hot Tub

4.86 out of 5 average rating, 221 reviews

Home in Woodstock

Cozy Woodstock Retreat—Near Village & Fireplace

5 out of 5 average rating, 45 reviews

A spacious open-plan living area is showcased, featuring large windows that invite natural light. A modern sectional sofa in warm tones is arranged around a low table. A dining area with a long table and dining chairs is visible in the background, enhancing the inviting atmosphere.

Home in Egremont

The Catamount Ski Haus with Pool & Hot Tub

4.94 out of 5 average rating, 139 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.

4.91 out of 5 average rating, 33 reviews

A spacious outdoor area features a circular stone fire pit surrounded by a sectional seating arrangement. A gazebo and hot tub are visible in the background, along with scenic views of rolling hills under an expansive sky.

Home in Hillsdale

Hillsdale Escape | Pool, Hot Tub, Game Room

4.94 out of 5 average rating, 160 reviews

A charming farmhouse is framed by vibrant autumn foliage, with a wooden gate leading to a gravel path. Leaves strewn across the ground add to the seasonal ambiance, while the white exterior of the house is complemented by dark green accents.

Home

Spacious 5BR Catskill Retreat Near Saugerties Hike

5 out of 5 average rating, 58 reviews

A spacious living area is filled with natural light from large windows, offering views of the surrounding woodlands. A modern couch is positioned near a wood-burning stove, complemented by a contemporary dining table. Pendant lighting enhances the cozy atmosphere.

Home in Leeds

Birch & Buck - Stunning Views near Hudson & Hunter

4.95 out of 5 average rating, 109 reviews

A spacious living area features a hand-built stone fireplace adorned with decorative elements. Large windows allow natural light to fill the room, which includes a dining space with a long table set for guests. Comfortable seating is positioned around the fireplace on a well-defined area rug.

Home in Saugerties

MODERN FARMHOUSE in the WOODS

Apartment rentals with a pool

4.89 out of 5 average rating, 99 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.

Apartment in Hunter

Cozy Gem with Mountain Views

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, 122 reviews

Windham Condo

4.9 out of 5 average rating, 220 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

A spacious living area is illuminated by large windows showcasing mountain views. A comfortable sofa and two plaid chairs are arranged around a wooden coffee table. Warm light is provided by a standing lamp, and a flat-screen TV sits on a brick fireplace console.

Apartment in Lanesville

Hunter Mountain 2BR Penthouse | Vaulted Ceilings

A spacious living area is furnished with a plaid armchair, a wooden coffee table, and a comfortable sofa. A dining table with four chairs faces a kitchen equipped with modern appliances. Natural light enters through the window, and light-colored walls create an open atmosphere.

Apartment in Lanesville

Hunter Mountain 1BR Suite | Jacuzzi & Fireplace

Superhost

4.73 out of 5 average rating, 291 reviews

Cozy Condo w/wood burning fireplace

A cluster of two-story condos is set against a backdrop of lush greenery. The modern structures exhibit a combination of dark and light materials, with large windows that reflect the sunny sky. Neatly trimmed landscaping enhances the welcoming exterior.

Apartment in Hunter

Entire condo in Hunter NY, Gorgeous area- sleeps 6

A spacious sectional couch, upholstered in dark fabric, is arranged around a glass coffee table. The wall is decorated with three art pieces featuring deer antler silhouettes. Light cream curtains frame a window, and a lamp provides additional lighting in the cozy seating area.

4.8 out of 5 average rating, 15 reviews

Ski Windham Mountain ( Catskills, NY)

Other holiday rentals with a pool

4.96 out of 5 average rating, 25 reviews

A spacious living area features a large pool table with a vibrant red felt surface. A round dining table with four yellow chairs is positioned in front of a bright window. A cozy sofa and an armchair offer comfortable seating, complemented by artistic decor and wooden flooring.

Barn in Pine Plains

Stunning horse farm apt, hot tub

4.71 out of 5 average rating, 31 reviews

The kitchen features bright cabinetry and stainless steel appliances. An island countertop is centrally positioned, complemented by a spacious layout that allows for easy movement. Natural wood flooring adds warmth and continuity to the space, while ample natural light brightens the area.

Home in Athens

Peaceful, Low Toxin Haven

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, 64 reviews

Modern Glass House

4.94 out of 5 average rating, 51 reviews

A barn exterior is depicted, showcasing a large, partially open window with a cross-braced design. The soft grey wood siding contrasts with the light pink trim around the window. A circular vent is visible above, contributing to the barn's rustic charm.

Home in Germantown

Hudson Valley Barn Getaway - Germantown

Guest house in Great Barrington

The studio interior features a spacious layout with a plush queen bed dressed in crisp white linens. A cozy reading chair sits in the corner, while natural light fills the room through large windows. A ceiling fan offers added comfort, and wood accents enhance the warmth of the space.

4.9 out of 5 average rating, 10 reviews

Poolside Long Pond Bungalow!

4.98 out of 5 average rating, 49 reviews

A winding pathway leads through verdant greenery towards a striking red cabin, surrounded by trees. The cabin features large front windows and a welcoming porch, set against a bright blue sky. Sunlight filters through the foliage, creating a serene outdoor atmosphere.

Cottage in Athens

The Cabbage ~ A place to create/relax/restore.

4.92 out of 5 average rating, 96 reviews

Hudson River Sunset Getaway