House holiday rentals in 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, 354 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.

5 out of 5 average rating, 126 reviews

A cozy living area is presented, featuring a soft beige sofa and a light armchair beside a wooden coffee table. A green plant adds a natural touch, and a light fixture hangs from the ceiling, while soft light filters in from a nearby window.

Home in Beacon

Beacon Creek House

Welcome to our serene oasis in Beacon, NY. If Gilmore Girls and Schitt’s Creek had a baby, it would be Beacon. Nestled beside a tranquil creek, our home features 2 cozy bedrooms, a stylish bathroom, and an open living space with a daybed. Designed with wabi-sabi aesthetics and eco-friendly materials. Just steps from Main Street and less than a 5 min drive from the train station, with scenic trails, shops and restaurants nearby. Book your stay and experience our artfully designed home and city!

4.88 out of 5 average rating, 935 reviews

Home in Kerhonkson

Forest Retreat in the Gunks | Cozy Mountain Escape

Set on the side of the Gunks and surrounded by quiet forest, this warm, cozy home is designed for guests who love nature and simple comfort. Just minutes from Minnewaska and Stony Kill Falls. Enjoy wood-burning stove, a handmade L-couch, premium queen mattresses, a forest-view kitchen stocked with high quality coffee, tea, and essentials. Thoughtful touches include incense, essential oils, Puracy toiletries, and a meaningful library. Two porches facing the woods create a warm, peaceful escape.

4.99 out of 5 average rating, 149 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, 141 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, 113 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.

A charming cottage is framed by trees, with a welcoming yellow door nestled among the greenery. A stone pathway leads to the entrance, bordered by well-maintained grass. Natural light filters through the surrounding foliage, enhancing the peaceful ambiance of the setting.

4.94 out of 5 average rating, 154 reviews

Peaceful Yellow Door Cottage

Yellow Door Cottage is a quiet family getaway nestled in the woods, but close to the historic Village of Cold Spring. Large backyard, ideal for afternoon lunch on the deck or an evening around the fire. Located on a lovely country road, great for walking and biking. 3 comfy bedrooms with linens supplied. Wi-Fi, TVs, washer/dryer, close to amazing hikes and the beautiful Hudson River! Rent alone or pair with my cottage next door: Cheerful Private 3 Bedroom Cottage in Cold Spring on Airbnb.

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.

4.86 out of 5 average rating, 123 reviews

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. Enjoy shopping, farms,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, 177 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.

A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.

4.99 out of 5 average rating, 183 reviews

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

A charming two-story house features a combination of red siding and stone accents. A welcoming porch with white railings leads to the front door. Lush greenery surrounds the entrance, enhancing the inviting exterior. Nearby, a well-maintained lawn adds to the home's appeal.

4.99 out of 5 average rating, 131 reviews

The Little Red House

Located in a quiet neighborhood just off the Hudson River, yet only a 10 min drive from the bustling town of Beacon and within walking distance to the Newburgh action where you will find restaurants, coffee shops, galleries local shopping, and nightlife. With countless hiking spots, farms, breweries, and wineries, your stay in Hudson Valley will be memorable. The house was also a filming & staging location for the movie “Adults” starring Michael Cera

A spacious living room features a soft, light-colored couch and a small wooden coffee table. A flat-screen TV is mounted on the wall, while decorative shelves display greenery and art. Natural light streams in through windows dressed with sheer curtains.

4.92 out of 5 average rating, 124 reviews

Lovely home in town of Newburgh

PLEASE READ FULL DESCRIPTION PRIOR TO BOOKING! Welcome to our cozy and stylish home located in the town of Newburgh. This modern space offers comfort and convenience with a fully equipped kitchen, comfortable beds, washer & dryer, and a central location close to shops and restaurants. Perfect for both business and leisure travelers.

Popular amenities for Philipstown house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 517 reviews

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

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.

4.83 out of 5 average rating, 113 reviews

Entire Home (private pool), Event Friendly

4.98 out of 5 average rating, 101 reviews

A spacious living area features large windows that provide natural light and views of the surrounding trees. Comfortable leather furniture includes a sofa and an armchair, arranged around a rustic coffee table on a textured area rug. A potted plant adds a touch of greenery.

Home in Bantam

Hilltop House w/POOL/SPA- HOST & Co.

4.89 out of 5 average rating, 182 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, 192 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, 103 reviews

An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.

Home in Accord

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

5 out of 5 average rating, 161 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, 177 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Weekly house rentals

Superhost

An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.

Home in Spring Glen

4.95 out of 5 average rating, 217 reviews

Creekside cottage on 65 acres of land

5 out of 5 average rating, 17 reviews

Mountainside Home (Beacon/Cold Spring)

4.96 out of 5 average rating, 792 reviews

A spacious living area showcases rich wooden paneling and high, sloped ceilings. A large leather sectional is arranged around a central wooden coffee table. Natural light streams through multiple windows, with a stylish fan overhead adding to the cozy ambiance.

Home in New Paltz

Victorian Haven

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 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.

4.94 out of 5 average rating, 32 reviews

Arkadia House Mid-century retreat with pool & view

A charming home nestled among trees features a spacious front porch adorned with planter boxes. Lush greenery and colorful flower beds surround the property, and a large boulder adds a natural element to the landscape.

5 out of 5 average rating, 75 reviews

Home in Cold Spring- Farm Stay!

4.93 out of 5 average rating, 75 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

5 out of 5 average rating, 18 reviews

Modern, sun-filled farmhouse retreat

Private house rentals

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, 39 reviews

Tranquil Hudson Valley Retreat with Cedar Hot Tub

Superhost

A living room features vibrant green walls and hardwood flooring. A yellow sofa is set in front of a fireplace, while a glass coffee table occupies the center. Shelving displays artwork and photos, complemented by a television on a stand and two accent chairs in the corner.

4.86 out of 5 average rating, 22 reviews

The Cardinal

A well-lit bedroom features a spacious white bed, complemented by light green curtains that frame a large window. A simple ceiling fan is installed for ventilation. The adjacent hallway leads to a cozy living area, showcasing a neutral color palette and decorative elements.

4.92 out of 5 average rating, 60 reviews

Welcome to Newburgh's Cozy Cove

A rustic cabin is nestled among lush greenery, featuring a screened-in porch with a staircase leading up to it. Stone steps are visible at the entrance, with a small garden area surrounding the base. The cabin blends with its natural surroundings.

4.9 out of 5 average rating, 49 reviews

Cabin with a View

4.93 out of 5 average rating, 73 reviews

Winter by the Fire in Cold Spring

4.98 out of 5 average rating, 42 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

4.89 out of 5 average rating, 64 reviews

Home in Beacon

Cozy Studio in a Great Location!

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.