House holiday rentals in Town of Philipstown

A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.

4.95 out of 5 average rating, 350 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station. From here, you can get to Manhattan in an hour and 10 minutes. Occasionally our two small hypoallergenic dogs are with us in the house — one toy poodle and one shih tzu. If you'd like to bring your dog(s), this is a pet friendly home! Our dogs will not stay here when you visit, of course.

4.94 out of 5 average rating, 364 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

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.99 out of 5 average rating, 161 reviews

A modern living area features a gray sofa with tufted seating, positioned near a wooden coffee table. Exposed wooden beams span the ceiling, while a cozy rattan chair adds warmth. Natural light streams through windows, creating a bright and airy ambiance.

Home in Beacon

NEW! Stylish Home in the Heart of Beacon

This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

4.99 out of 5 average rating, 141 reviews

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

A wooden exterior house is surrounded by trees displaying autumn foliage. A pathway of stones leads to the entrance, where a deck with white railings is visible. Lush shrubs and decorative rocks enhance the natural landscaping.

4.94 out of 5 average rating, 139 reviews

Cozy 3 bedroom house on quiet private road

3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahenstock St Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay. I live close by so I’m available for help or assistance during your stay.

4.99 out of 5 average rating, 310 reviews

The entrance of the cottage is framed by lush greenery and vibrant foliage. A stone pathway leads to a welcoming front door, accentuated by an overhanging roof and outdoor lighting. The architectural details are complemented by the surrounding natural landscape.

Home in Kerhonkson

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature. Hosted by The Reset Club, a member of 1% for the Planet.

4.99 out of 5 average rating, 108 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

The exterior of a cottage is presented, featuring a gravel driveway and a single garage. Surrounding trees showcase autumn foliage while a small wooden deck is visible above the garage. The mountains can be seen in the distance beneath a partly cloudy sky.

4.86 out of 5 average rating, 136 reviews

Bear Mtn Haus near hiking trails

Welcome to our cozy and thoroughly cleaned Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, just 60min from NYC, 15 min to Cold Spring shops and restaurants, 8 min drive from the Garrison train stop. Set on the mountainside, we have lovely partial views of the Hudson river. Short drive to Woodbury Commons Premium Outlet mall and close to Storm King, and Beacon. Our house is suitable for 6 people, but can accommodate 8 at an extra charge.

4.98 out of 5 average rating, 131 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

4.86 out of 5 average rating, 119 reviews

A charming two-story house is featured with a light yellow facade and white trim. A welcoming front porch with a bench overlooks the neatly landscaped yard, filled with greenery and flower beds. The inviting entrance is flanked by large windows and decorative shutters.

Home in Newburgh

Lady Montgomery

Enjoy our trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that the Hudson Valley has to offer like shopping, hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes to help you explore. Everyone will enjoy their time in this comfortable artistic home!

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

4.95 out of 5 average rating, 175 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

4.93 out of 5 average rating, 261 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Popular amenities for Town of Philipstown house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 199 reviews

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

Private Hudson Valley Country Retreat

4.98 out of 5 average rating, 514 reviews

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

4.83 out of 5 average rating, 110 reviews

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home (private pool), Event Friendly

4.89 out of 5 average rating, 175 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

4.88 out of 5 average rating, 185 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

5 out of 5 average rating, 160 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

5 out of 5 average rating, 174 reviews

The exterior of a charming guesthouse is illuminated during twilight, with warm string lights hanging above a patio area. Large windows reveal the inviting interior, while tall trees frame the scene, creating a serene atmosphere in the evening.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

4.92 out of 5 average rating, 157 reviews

Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Weekly house rentals

The exterior of a wooden two-story house is framed by lush greenery and a landscaped garden. A prominent tree and rock-bordered flower beds are visible in the foreground. Large windows reflect soft light from within, contributing to a welcoming atmosphere.

4.96 out of 5 average rating, 56 reviews

Cold Spring Modern Country House

An evening deck scene is illuminated by soft string lights, offering a welcoming ambiance. A modern grill sits beside potted plants, with views of trees and distant hills captured against the twilight sky.

4.95 out of 5 average rating, 37 reviews

Tranquil Hudson Valley Retreat with Cedar Hot Tub

A spacious multi-story house is shown, featuring dark wood siding and large windows. A broad staircase leads to an inviting deck with outdoor seating. Lush greenery surrounds the property, while a gravel path guides visitors to a generous wooden table set in the yard.

5 out of 5 average rating, 7 reviews

Nordic escape among tree tops

A concrete pier extends over the tranquil water, featuring two lounge chairs positioned for relaxing views of the river and surrounding landscape. Lush greenery and distant homes are visible across the water, enhancing the peaceful outdoor setting.

4.73 out of 5 average rating, 170 reviews

Bungalow near West Point on Hudson River

4.98 out of 5 average rating, 41 reviews

A spacious living area is highlighted by large glass doors, offering views of the surrounding greenery. A wooden coffee table occupies the center, complemented by two comfortable sofas adorned with light-colored cushions. Natural light fills the room, enhancing the airy feel.

Home in Putnam Valley

Sunny house on Lake Oscawana

5 out of 5 average rating, 54 reviews

Home in Highland Falls

Billy Joel/JP Morgan Hudson Valley Home 1h to NYC

A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.

4.93 out of 5 average rating, 29 reviews

Arkadia House Mid-century retreat with pool & view

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

4.86 out of 5 average rating, 78 reviews

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More

Private house rentals

4.85 out of 5 average rating, 67 reviews

The spacious living room features high cathedral ceilings with large A-frame windows that provide abundant natural light. A cozy fireplace is positioned beneath a wall-mounted TV. Warm wood flooring complements the inviting atmosphere, creating a perfect space for relaxation and gathering.

Home in Carmel Hamlet

Dog & Family Friendly A-Frame - Private and Cozy

4.98 out of 5 average rating, 46 reviews

The kitchen features modern navy cabinetry and a large island with seating for four. Stainless steel appliances, including a fridge and oven, are complemented by quartz countertops. Natural light illuminates the space through a window overlooking the yard.

Home in Beacon

Central Beacon Retreat: Hot Tub & Chef's Kitchen

5 out of 5 average rating, 86 reviews

A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.

Home in Highland Falls

Modern Usma Home, Walk to West Point. Hot Tub!

A modern kitchen is presented with custom stainless cabinetry and a large gas range. Floating walnut shelves hold various kitchenware. The checkered floor features green and cream tiles. Windows allow natural light, creating a bright atmosphere within the space.

5 out of 5 average rating, 8 reviews

Cozy Modern Winter Retreat | Hudson Valley

A modern wooden home is surrounded by vibrant autumn foliage, featuring large windows that invite natural light into the interior. Two wooden chairs are positioned on a patio area, complementing the serene outdoor setting.

5 out of 5 average rating, 27 reviews

Cold Spring Hidden Gem: woods, walk to town, SAUNA

4.99 out of 5 average rating, 83 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

4.94 out of 5 average rating, 70 reviews

A stone patio is shown with six colorful chairs arranged around a fire pit. In the background, trees and a trampoline are visible, contributing to a serene outdoor setting, ideal for gathering and relaxation.

Home in Mohegan Lake

A nice place to getaway

A cozy bedroom features a spacious bed adorned with a colorful patterned quilt. Natural light enters through large windows, illuminating the wooden floors. A bedside table holds a lamp, while double glass doors provide access to a serene outdoor space.