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Pet-friendly holiday rentals in Sleepy Hollow

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Sleepy Hollow

  • Nightly prices starting at

    Sleepy Hollow holiday rentals start at $305 NZD per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sleepy Hollow rentals

  • 4.8 Average rating

    Sleepy Hollow stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Sleepy Hollow

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

PetsWalkabilityLocation

4.91 out of 5 average rating, 144 reviews
Guest favourite
Townhouse in White Plains

Charming 3BR Home - Quiet Stay, Close to NYC

Welcome to your White Plains retreat- a beautifully renovated townhouse designed for convenience and a relaxing stay. Perfect for families or small groups, the home features a modern kitchen, three cozy bedrooms, and inviting spaces that truly feel like home. Just a 12-minute walk to North WP Station, you can reach Manhattan in about 45 minutes while still enjoying the restaurants, shops, and charm of Westchester. As Airbnb Superhosts, we’re dedicated to making every stay seamless and memorable.

WalkabilityPetsFamily

4.95 out of 5 average rating, 138 reviews
Superhost
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

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

PetsWalkabilityGetting around

4.84 out of 5 average rating, 168 reviews
Top Guest favourite
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

PetsOutdoor spacesQuiet

4.99 out of 5 average rating, 190 reviews
Top Guest favourite
A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.
Home in Norwalk

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

Outdoor spacesPetsBathroom

4.98 out of 5 average rating, 141 reviews
Guest favourite
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.

Outdoor spacesPetsAccess

4.94 out of 5 average rating, 138 reviews
Top Guest favourite
Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Outdoor spacesPetsComfort

4.98 out of 5 average rating, 130 reviews
Top Guest favourite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

Outdoor spacesPetsSleep quality

4.96 out of 5 average rating, 557 reviews
Top Guest favourite
Apartment in Yonkers

Sweet & Cozy Home | Free parking

Public transportation just minutes away—bus steps from the home and train very close. Sweet & Cozy Home only 30 minutes from Manhattan. Welcome to your home away from home in Yonkers, NY. This two-floor apartment is perfect for families or groups, offering three comfortable bedrooms, a fully equipped kitchen, a cozy living room with Smart TV, and a private porch for morning coffee or evening relaxation. Easy commute to Manhattan, Bronx Zoo, Yankee Stadium, and other NYC attractions.

PetsWalkabilityCondition

4.99 out of 5 average rating, 112 reviews
Guest favourite
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 spacesPetsHospitality

4.95 out of 5 average rating, 135 reviews
Top Guest favourite
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

PetsWalkabilityBackyard

4.97 out of 5 average rating, 247 reviews
Top Guest favourite
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

Enjoy this stylish home located less than a 10 minute drive from many walking/biking trails and tons of restaurants and local entertainment. It is also a 2 minute drive from the NY Presbyterian Hudson Valley Hospital perfect for Traveling Nurses and other short-term healthcare professionals. The neighborhood is quiet and situated at the end of a cul-de-sac, so there is no through traffic, suitable for walking your dog.

WalkabilityPetsQuiet

4.97 out of 5 average rating, 126 reviews

Popular amenities for Sleepy Hollow pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
A modern kitchen is equipped with stainless steel appliances and granite countertops. Upper cabinets with illuminated displays complement the warm-toned backsplash. A vase filled with fresh flowers enhances the countertop space, while the polished wood flooring stretches across the area.
Home in Mamaroneck

Entire 4BR House, Walk to Train! Yard + Parking

Outdoor spacesWalkabilityCleanliness

4.99 out of 5 average rating, 113 reviews
Superhost
Home in Stamford

5BR Beach House, Game Room + Huge Backyard

PetsWalkabilityLong stay

4.94 out of 5 average rating, 108 reviews
Top Guest favourite
A rustic wooden house is set amidst lush greenery, featuring a fieldstone chimney that rises prominently from the side. Large windows allow natural light to enter, and a doorway leads to the outdoors. The sloped grass yard leads up to the residence, enhancing its country charm.
Home in Mount Kisco

Incredible barn in country setting

Outdoor spacesPetsCondition

4.94 out of 5 average rating, 159 reviews
Top Guest favourite
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!

WalkabilityOutdoor spacesCheckout

4.95 out of 5 average rating, 368 reviews
Top Guest favourite
A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.
Home in Carmel Hamlet

Lux Bungalow on the Lake

WalkabilityOutdoor spacesView

4.93 out of 5 average rating, 230 reviews
Top Guest favourite
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!

WalkabilityPetsKitchen

4.99 out of 5 average rating, 114 reviews
Superhost
A spacious backyard features a heated pool surrounded by a stone patio, overlooking the scenic lake. Vibrant fall foliage adorns the landscape, and the serene water reflects the clear sky. A cozy home is visible, nestled against the lush greenery.
Home in Greenwood Lake

Luxury Villa w Lake View & Private Heated Pool

PetsOutdoor spacesCondition

4.91 out of 5 average rating, 116 reviews
Guest favourite
A modern kitchen is featured with wooden cabinetry and a white countertop. A stainless steel gas stove is positioned next to a microwave. A small cart holds kitchen supplies, while a window above the sink allows natural light to enter into the space.
Home in Yonkers

Cozy 2 Bedroom Lower Level Apartment

PetsWalkabilityCheck-in

4.76 out of 5 average rating, 357 reviews

Pet-friendly home rentals with a pool

Guest favourite
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

PetsWalkabilityCheck-in

4.97 out of 5 average rating, 224 reviews
Guest favourite
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 spacesPetsGetting around

4.96 out of 5 average rating, 145 reviews
Guest favourite
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

WalkabilityOutdoor spacesTV

4.82 out of 5 average rating, 107 reviews
Guest favourite
Home in Beacon

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

Outdoor spacesPetsAccess

4.92 out of 5 average rating, 180 reviews
Top Guest favourite
Home in New Windsor

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

Outdoor spacesPetsBackyard

5.0 out of 5 average rating, 105 reviews
Top Guest favourite
A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.
Farm stay in Redding

Charming Historic Cottage in the Redwoods

WalkabilityOutdoor spacesCondition

4.98 out of 5 average rating, 102 reviews
Top Guest favourite
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

PetsOutdoor spacesGetting around

5.0 out of 5 average rating, 187 reviews
Top Guest favourite
Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

WalkabilityPetsSolo travel

4.99 out of 5 average rating, 186 reviews

Private, pet-friendly home rentals

Guest favourite
The sleeping area contains two full beds with patterned bedding. A small couch is positioned beside the beds, accompanied by a side table and a kitchenette area in the corner. Natural light enters through glass doors leading to the outdoor space.
Guest suite in Hastings-on-Hudson

Adorable 1 Bedroom 2-Bed suite near NYC

PetsWalkabilityHiking

4.91 out of 5 average rating, 148 reviews
Guest favourite
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

WalkabilityOutdoor spacesBarbecue

4.97 out of 5 average rating, 227 reviews
Top Guest favourite
A spacious bedroom is presented, featuring a sizable bed dressed in soft white linens and accented by numerous decorative pillows. Two lamps provide gentle illumination on either side, while artwork adorns the walls. A wooden bench is positioned at the foot of the bed.
Apartment in New Rochelle

Woven Winds Retreat

Outdoor spacesPetsSleep quality

4.99 out of 5 average rating, 199 reviews
Top Guest favourite
Apartment in Yonkers

Spacious 3BR • Sleeps 12 • Near NYC Train + Parkin

Outdoor spacesWalkabilityBathroom

4.93 out of 5 average rating, 174 reviews
Guest favourite
Chalet in Cold Spring

Mountain View Retreat

WalkabilityOutdoor spacesAccuracy

4.9 out of 5 average rating, 516 reviews
Guest favourite
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

PetsOutdoor spacesCleanliness

4.88 out of 5 average rating, 329 reviews
Top Guest favourite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Greenwood Lake

Cabinessence -on Greenwood Lake, NY #34370

PetsWalkabilityLaundry

4.96 out of 5 average rating, 497 reviews
Top Guest favourite
A scenic view of the river is framed by lush greenery and trees. Nearby buildings can be seen, with one featuring a sloped roof and another brick structure. The calm water reflects the blue sky and surrounding hills.
Apartment in Hastings-on-Hudson

Spacious apartment in Hastings-on-Hudson near NYC

WalkabilityPetsBathroom

4.98 out of 5 average rating, 157 reviews

Destinations to explore