Pet-friendly holiday rentals in Philipstown

4.99 out of 5 average rating, 152 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Outdoor spacesPetsAmenities

4.9 out of 5 average rating, 276 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.

PetsOutdoor spacesHeating

4.99 out of 5 average rating, 109 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 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

Outdoor spacesWalkabilityTV

4.99 out of 5 average rating, 185 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

WalkabilityOutdoor spacesHeating

4.99 out of 5 average rating, 373 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

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

PetsWalkabilityTV

4.88 out of 5 average rating, 324 reviews

A striking wooden wall showcases a large bank of windows offering panoramic views of Lake Oscawana and surrounding foliage. The vaulted ceiling emphasizes the spaciousness of the room, inviting natural light to fill the space.

Cottage in Putnam Valley

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

PetsWalkabilityDecor

4.98 out of 5 average rating, 287 reviews

A serene outdoor seating area features two wooden chairs positioned beside a stone platform. A fire pit with a crackling flame is set in front of the chairs, overlooking a gently flowing creek and lush greenery, creating a tranquil nature retreat.

Cabin in Millrift

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

Outdoor spacesWalkabilityCheckout

4.94 out of 5 average rating, 137 reviews

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

PetsOutdoor spacesDecor

4.95 out of 5 average rating, 131 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

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Outdoor spacesPetsHeating

4.95 out of 5 average rating, 367 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!

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.

Outdoor spacesWalkabilityGetting around

4.81 out of 5 average rating, 102 reviews

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.

Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Escape the hustle and bustle of city life and unwind in the peaceful surroundings of this luxurious retreat. With a sauna, steam room, and pool, our home offers something for everyone. Whether you are enjoying the spa like amenities or cozying up by the wood-burning stove you will have an incredible time staying with us. Don't wait, book your perfect getaway now and recharge your mind, body, and soul at our idyllic oasis!

WalkabilityPetsAccuracy

4.9 out of 5 average rating, 512 reviews

Chalet in Cold Spring

Mountain View Retreat

15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

PetsOutdoor spacesBathroom

Popular amenities for Philipstown pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5.0 out of 5 average rating, 103 reviews

The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.

Home in Highland Falls

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

PetsWalkabilityLocation

4.94 out of 5 average rating, 144 reviews

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.

Home in Philipstown

Creekside Home Near Cold Spring & West Point

Outdoor spacesPetsCheck-in

4.96 out of 5 average rating, 109 reviews

Home in Kerhonkson

Luxe modern A Frame, Hot tub and new heated pool

Outdoor spacesPetsSleep quality

4.95 out of 5 average rating, 366 reviews

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

PetsOutdoor spacesBiking

4.96 out of 5 average rating, 281 reviews

A functional kitchen features wooden cabinetry with a warm finish and a light-colored countertop. A stainless steel refrigerator is positioned alongside a compact microwave. The tile flooring adds practicality to the space, while a window with a lace curtain allows natural light to enter.

Home in Beacon

Mt hikes, city strolls river walks

Outdoor spacesWalkabilityHiking

4.92 out of 5 average rating, 141 reviews

An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.

Home in Putnam Valley

Crystal Wave LakeHouse

PetsOutdoor spacesGetting around

4.84 out of 5 average rating, 168 reviews

The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.

Home in Ossining

Lower Hudson Valley Idyllic Retreat

PetsOutdoor spacesAccess

4.94 out of 5 average rating, 246 reviews

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

Creekside cottage on 65 acres

PetsWalkabilityQuiet

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 178 reviews

Home in Beacon

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

Outdoor spacesWalkabilityCleanliness

4.96 out of 5 average rating, 143 reviews

A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.

Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Outdoor spacesPetsBarbecue

5.0 out of 5 average rating, 102 reviews

Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Outdoor spacesPetsBarbecue

4.8 out of 5 average rating, 132 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 Indoor Pool

PetsOutdoor spacesDecor

4.88 out of 5 average rating, 226 reviews

A spacious living area exhibits warm wooden floors and large windows adorned with decorative curtains. A cozy futon is positioned on a textured rug, complemented by a decorative welcome sign on the wall. A spiral staircase leads to the upper level, enhancing the open layout.

Apartment in Stony Point

E and T Getaway LLC

PetsOutdoor spacesCheckout

4.97 out of 5 average rating, 221 reviews

A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.

Guest suite in Holmes

Huge eclectic space w/ private pool. 1.5hr to city

WalkabilityPetsLocation

5.0 out of 5 average rating, 187 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 salt pool/sauna

Outdoor spacesWalkabilityAccess

4.99 out of 5 average rating, 328 reviews

The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.

Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

WalkabilityOutdoor spacesIndoor spaces

Private, pet-friendly home rentals

4.97 out of 5 average rating, 242 reviews

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

WalkabilityOutdoor spacesBathroom

4.89 out of 5 average rating, 270 reviews

Apartment in Newburgh

Special Nest w Private Entrance River View Porches

Outdoor spacesWalkabilityQuiet

4.96 out of 5 average rating, 452 reviews

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

PetsWalkabilityAmenities

4.96 out of 5 average rating, 102 reviews

A spacious studio features a comfortable bed with a decorative throw blanket. A dining table is surrounded by patterned chairs. The kitchen area is visible in the background, and a staircase leads to a loft space. Natural light brightens the room, enhancing the wooden details.

Guesthouse in Beacon

Spacious Trailside Studio

PetsOutdoor spacesBiking

Farm stay in Fort Montgomery

A charming house trailer is shown with white trim and multiple windows, surrounded by trees. An outdoor wooden deck features a grill, purple chairs, and a small pumpkin. Steps lead up to the entrance, offering access to the inviting outdoor space.

4.97 out of 5 average rating, 249 reviews

Secluded overlook cottage near West Point

PetsWalkabilityHospitality

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.

4.8 out of 5 average rating, 568 reviews

Cozy getaway in Cold Spring

PetsOutdoor spacesWi-Fi

4.96 out of 5 average rating, 382 reviews

Townhouse in Beacon

Pet-Friendly 3BR Retreat – Walk to Shops & Cafe

PetsOutdoor spacesAccuracy