Pet-friendly holiday rentals in West Point

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.

4.99 out of 5 average rating, 112 reviews

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 spacesPetsDecor

Home in Cornwall-on-Hudson

A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.

4.99 out of 5 average rating, 125 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

WalkabilityPetsHospitality

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.

4.81 out of 5 average rating, 134 reviews

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Outdoor spacesPetsQuiet

The exterior of the house is surrounded by trees, with a welcoming front porch featuring chairs. A circular stone fire pit area is visible in the yard, complemented by a gravel surface and wooden adirondack chairs. The driveway is paved and leads to the garage.

4.97 out of 5 average rating, 112 reviews

West Point Mountain House

Welcome to West Point! Enjoy early check-in in and late check out at our beautiful mountainside house overlooking the village on its own private hill. Spacious and cozy, this home is great for large families or groups of friends coming to explore West Point, Bear Mountain, Storm King, or the Hudson Valley at large. Just 1 hour from NYC and minutes away from restaurants and local attractions. This 3500 Sq Ft home features fun for everyone in a private setting, but still close to all the fun!

Outdoor spacesWalkabilityCheck-in

4.85 out of 5 average rating, 372 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!

WalkabilityOutdoor spacesParking

Home in Cornwall-on-Hudson

The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.

4.93 out of 5 average rating, 190 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

WalkabilityPetsRiver

Apartment in Cornwall-on-Hudson

A wooden porch leads to a vibrant purple door, framed by light-colored trim. Potted red flowers add color to the entrance, while natural light filters through the nearby trees, highlighting the rustic charm of the space.

4.98 out of 5 average rating, 246 reviews

Charming Efficiency

Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

Outdoor spacesWalkabilityIndoor spaces

Farm stay in Fort Montgomery

A circle of bright orange Adirondack chairs surrounds a fire pit, which is highlighted by flickering flames. Lush green grass extends beneath the chairs, complemented by scattered yellow wildflowers. In the background, tall trees create a natural border under a clear blue sky.

4.93 out of 5 average rating, 288 reviews

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

Outdoor spacesPetsHiking

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, 209 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.

WalkabilityPetsQuiet

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.

5.0 out of 5 average rating, 105 reviews

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

Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

PetsOutdoor spacesValue

The living room features a combination of a black sofa and a light gray couch, adorned with red accent pillows. A wooden coffee table is positioned in the center, and light from a nearby window illuminates the space, complemented by a ceiling fan and wall-mounted television.

4.8 out of 5 average rating, 138 reviews

Lovely 3BR Home with parking-Walk to WP Gate!

Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

WalkabilityPetsBreakfast

4.97 out of 5 average rating, 245 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

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Outdoor spacesWalkabilityLaundry

Popular amenities for West Point pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.82 out of 5 average rating, 107 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

WalkabilityPetsHiking

5.0 out of 5 average rating, 105 reviews

Home in New Windsor

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

PetsOutdoor spacesWi-Fi

4.92 out of 5 average rating, 145 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

Outdoor spacesWalkabilityHeating

4.99 out of 5 average rating, 189 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

WalkabilityOutdoor spacesParking

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

PetsOutdoor spacesValue

A private hot tub sits on a cement pad, surrounded by greenery and trees. In the background, lounge chairs are arranged in a clearing, adding to the serene outdoor setting.

4.93 out of 5 average rating, 108 reviews

Charming Getaway 16mi to West Point!

Outdoor spacesPetsQuiet

4.84 out of 5 average rating, 264 reviews

Escape NYC! Spacious Withers Mansion Hudson Valley

PetsOutdoor spacesWi-Fi

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 spacesPetsCheckout

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 135 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

PetsOutdoor spacesValue

4.96 out of 5 average rating, 141 reviews

A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.

Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Outdoor spacesWalkabilitySleep quality

4.97 out of 5 average rating, 224 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

PetsOutdoor spacesKitchen

4.94 out of 5 average rating, 102 reviews

Cabin in Montgomery

Historic Cabin with Pool and Fire Pit

Outdoor spacesPetsHiking

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)

PetsOutdoor spacesValue

4.98 out of 5 average rating, 547 reviews

The exterior of a Mid Century Mod house is showcased at night, illuminated by soft outdoor lights. The building features large windows that reveal glimpses of the interior, while the surrounding lawn is landscaped with grass and scattered fallen leaves.

Home in New Paltz

midcentury mod hot tub*walk out trail R2R/Mohonk

Outdoor spacesPetsHeating

4.89 out of 5 average rating, 208 reviews

Cabin in Kerhonkson

Hot Tub - Sauna - Arcade- Fireplace - Pool Open

PetsOutdoor spacesLaundry

4.92 out of 5 average rating, 155 reviews

An aerial view captures a stylish retreat surrounded by lush greenery. A wooden deck outlines a rectangular saltwater pool, accompanied by lounge chairs and large umbrellas. A shaded seating area is positioned nearby, promoting outdoor relaxation.

Home in Kerhonkson

Mid Century Mod 5-Bed, Pool OPEN!, Dogs Welcome

Outdoor spacesPetsAmenities

Private, pet-friendly home rentals

4.97 out of 5 average rating, 225 reviews

A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.

Cottage in Philipstown

Modern Country Cottage by Bear Mountain

WalkabilityPetsComfort

4.96 out of 5 average rating, 388 reviews

Townhouse in Beacon

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

Outdoor spacesWalkabilityIndoor spaces

4.98 out of 5 average rating, 120 reviews

Apartment in Newburgh

Centrally Located in the Heart ❤ of Newburgh

PetsWalkabilityHeating

4.98 out of 5 average rating, 129 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

Outdoor spacesPetsCheckout

Guest suite in Fort Montgomery

A sweeping view of the Hudson River framed by vibrant autumn foliage. The landscape showcases a mix of red, orange, and yellow trees with hills in the background, creating a tranquil natural setting. Mist softly blankets the distant mountains.

4.94 out of 5 average rating, 492 reviews

West Point - Mountain Top Suite

WalkabilityPetsCheckout

4.89 out of 5 average rating, 415 reviews

An inviting front porch features a comfortable bench and potted plants. The view captures a gravel path leading to a barn and lush greenery, with a gentle rain enhancing the tranquil atmosphere.

Farm stay in Goshen

Bright Farm House- Tranquil setting

WalkabilityOutdoor spacesSleep quality

4.97 out of 5 average rating, 125 reviews

A single-story home in a vibrant pink hue showcases a unique oval front door, flanked by dark shutters. A concrete pathway leads to the entrance, surrounded by a well-maintained green lawn and partial wooden fencing in the background.

Home in Peekskill

Charming Home in Peekskill NY

Outdoor spacesWalkabilityBackyard