Family-friendly holiday rentals in Town of Philipstown

4.91 out of 5 average rating, 254 reviews

The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.

Apartment in Philipstown

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Guest suite in Wappingers Falls

The living area features a comfortable black leather couch positioned near a wooden coffee table. A large television is mounted on the wall opposite the seating. Light-colored walls and wood flooring create a spacious ambiance, with a door leading outside visible in the background.

4.83 out of 5 average rating, 126 reviews

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. Br/full bath/large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen. Car suggested.

4.89 out of 5 average rating, 661 reviews

The exterior of the Little Yellow Cottage features a charming yellow facade with white trim. A round window and a cupola add character to the roof. Surrounding greenery provides a natural setting, while a small white statue of a goat sits in front of the entrance steps.

Cottage in Highland

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Guest suite in New Windsor

The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.

4.96 out of 5 average rating, 257 reviews

Artistic Loft Private Home baked goodies

Features - 2 Super comfy queen sized beds. 2 Twin - Huge bathroom - Tub - Seated shower -Coffee/Tea/Snacks/Morning Muffins - Kitchenette - Private driveway. Parking at door. - Dedicated work desk. Wifi -Single traveler discount - Extra guest fee over 2 guests - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -35 min Bethel -Must be 25 years or older to book. No parties or gatherings. -6 guest maximum (inquire) -No 3rd party bookings

4.84 out of 5 average rating, 602 reviews

A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.

Loft in Mountainville

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

4.84 out of 5 average rating, 344 reviews

A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.

Apartment in Newburgh

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

4.97 out of 5 average rating, 330 reviews

A cozy room with a small kitchenette and a dining area featuring a round table and two chairs. Natural light fills the space through a glass door, which leads to the side yard. A minimalist wall art piece adds a touch of character to the room.

Guest suite in Beacon

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

4.96 out of 5 average rating, 356 reviews

A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.

Guest suite in Chester

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

4.94 out of 5 average rating, 149 reviews

A charming cabin with a red exterior is nestled among tall trees and autumn foliage. The building features multiple windows and a staircase leading to the entrance, while a rock border surrounds the lush ground cover and fallen leaves.

Cabin in Putnam Valley

Sweet, stylish cabin in the woods- hiking & more!

Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Guesthouse in Cold Spring

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

4.99 out of 5 average rating, 195 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Guest suite in Mountainville

A cozy studio space includes a queen bed with a light-colored coverlet. A kitchenette features essential appliances, complemented by a dining area with wooden table and black chairs. A flat-screen TV is mounted on the wall, and natural light brightens the room.

4.94 out of 5 average rating, 136 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

Guesthouse in Philipstown

A cozy sitting room features exposed wooden beams and a brick fireplace. Two comfortable leather chairs are arranged around a wooden coffee table. Natural light enters through multiple windows adorned with sheer curtains, illuminating the space, which is enhanced by decorative touches like artwork and plants.

4.99 out of 5 average rating, 119 reviews

Historic 1 bedroom home in Cold Spring, NY

This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

Popular amenities for Town of Philipstown family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 116 reviews

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.

Home in Newburgh

Lovely home in town of Newburgh

4.96 out of 5 average rating, 265 reviews

A hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.

Cottage in Bethel

Hot Tub, Playground, 3 Acres, and Much More!

4.87 out of 5 average rating, 134 reviews

A bright living room features high ceilings and large windows, providing natural light and views of the surrounding trees. Stylish designer furniture, including two armchairs and a dark sofa, complements a geometric artwork on the wall. A textured area rug enhances the space.

Home in Wallkill

Modern Upstate Gem Surrounded by Trees | Hot Tub

4.95 out of 5 average rating, 348 reviews

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.

Home in Cold Spring

Hilltop Hideaway Forest Villa on 13 acres!

4.95 out of 5 average rating, 407 reviews

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

Guesthouse in Beacon

Cozy Mountainside Suite - Minutes from Beacon

4.95 out of 5 average rating, 151 reviews

A serene cabin is nestled among trees, overlooking a private pond. The exterior features a mix of corrugated metal and wood, blending harmoniously with the natural surroundings. A spacious outdoor area includes a fire pit and seating, offering a tranquil retreat.

Cabin in Mountain Dale

Private lake cabin w/hot tub, views and fruit

4.9 out of 5 average rating, 484 reviews

Natural light floods a living area through large glass doors, which provide views of the garden and mountains. A comfortable couch faces a wooden coffee table, and a fireplace is situated beside a bookshelf filled with books. Decorative art enhances the space.

Chalet in Cold Spring

Mountain View Retreat

4.94 out of 5 average rating, 263 reviews

Two wooden Adirondack chairs are positioned on a grassy area, facing a serene landscape dotted with trees displaying autumn foliage. A small side table is set between the chairs, providing a space for refreshments. A shed is visible in the background among the greenery.

Apartment in Newburgh

Countryside Couples Suite

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 108 reviews

The exterior of the home is framed by green grass and colorful landscaping, featuring a stone wall and blooming yellow flowers in the foreground. Tall trees provide shade, while a clear sky with fluffy clouds creates a bright and inviting atmosphere.

Home in Highland Falls

Bear Mountain, Westpoint, & Hikers Retreat

4.96 out of 5 average rating, 622 reviews

An entrance to the barn loft is framed by rustic wooden walls and overhanging greenery. A glass-paneled door with a white frame offers a glimpse into the space, while a light-colored curtain is visible through the door, suggesting a warm interior.

Barn in Accord

Unique Barn Loft on Century Old Farm

4.94 out of 5 average rating, 106 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.89 out of 5 average rating, 379 reviews

The studio apartment is furnished with a Queen size bed dressed in neutral bedding, complemented by a cozy reclining chair. Brick walls and wooden accents create a warm environment. A small television is positioned for viewing, and a kitchenette area is visible in the corner.

Guest suite in Beacon

Cozy retreat, centrally located in Beacon NY

4.99 out of 5 average rating, 331 reviews

A tiny house with large windows is nestled among the trees, offering a secluded retreat. A wooden deck with stairs leads to the entrance. An outdoor dining space with an umbrella and a propane grill is visible alongside a gravel area, complemented by a playful dog on the lawn.

Tiny home in Wallkill

Get Away to "Hygge" Tiny House on 75 Private Acres

4.88 out of 5 average rating, 406 reviews

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

Sunset Bungalow-Mt views on 130acre forest & falls

4.91 out of 5 average rating, 783 reviews

A spacious bedroom is shown with a queen bed adorned in floral bedding. A cozy fireplace is built from natural stone, surrounded by decorative elements. A small breakfast table with black chairs is positioned near windows draped in bright yellow curtains, allowing natural light to fill the room.

Farm stay in New Paltz

The 1772 Lefevre Stonehouse Suite

Guest suite in Cold Spring

A serene sleeping area features a spacious bed covered with a patterned gray blanket. Nightstands are situated on either side, each equipped with lamps. Soft blue walls and a landscape painting enhance the calming ambiance. Natural light filters in through a window adorned with light drapes.

4.79 out of 5 average rating, 541 reviews

Cozy getaway in Cold Spring

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 245 reviews

An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

4.98 out of 5 average rating, 141 reviews

A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.

Apartment in Chester

Private Country Getaway

Apartment in Wappingers Falls

5 out of 5 average rating, 231 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

4.97 out of 5 average rating, 267 reviews

An outdoor area features a large swimming pool surrounded by a spacious patio, equipped with multiple lounge chairs. Colorful trees with autumn foliage outline the building, which showcases a triangular roof and multiple balconies. The sky is clear, reflecting the vibrant environment.

Condo in Vernon Township

Appalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony

4.93 out of 5 average rating, 367 reviews

A spacious main area is highlighted by a large bed covered with a floral quilt. A comfortable sofa is positioned nearby, while a wooden café counter with four chairs overlooks natural light coming through the three windows. A coffee bar and kitchen appliances are integrated into the space.

Apartment in New Paltz

Peaceful and Private Boutique Apartment *Pool*

Guesthouse in Pound Ridge

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

4.94 out of 5 average rating, 103 reviews

A Lovely Cottage in the Woods

4.92 out of 5 average rating, 294 reviews

A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.

Apartment in Brookfield

Peaceful apartment on 3.5 acres w/ Artist studio.