Pet-friendly vacation rentals in Sleepy Hollow

Find and book unique pet-friendly homes on Airbnb

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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Top guest favorite

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

4.93 out of 5 average rating, 129 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, Fahnestock State 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.

Top guest favorite

An inviting outdoor patio area is featured, shaded by a wooden structure. Decorative string lights hang overhead, while a variety of seating options are provided. Lush greenery and orange lilies enhance the landscaped garden, creating a peaceful and tranquil setting.

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

A serene river view is framed by tall trees, creating a natural canopy overhead. In the foreground, two Adirondack chairs are positioned on the grassy bank, inviting relaxation while overlooking the calm water surrounded by lush greenery.

Home in New Milford

4.97 out of 5 average rating, 106 reviews

Idyllic retreat on the water <1.5 hrs to NYC.

Private getaway on 3+ acres on the river with no visible neighbors, sit by the river or in the enclosed patio with view of the water, walk the trails in the area. Great for short escapes or longer discounted stays enjoy great restaurants, antiquing, swimming, hiking, and access to all New England has to offer. In spring, summer and fall lots of open air activities to be had. Fishing, boating, farmers markets and flea markets. In winter many nice walks to be had, skiing is not too far away.

Guest favorite

A panoramic view captures two distinct cottages nestled among autumn foliage. The left cottage features a light-colored facade and multiple windows, while the right cottage has a modern design with a dark exterior and skylights. A stone pathway leads through lush greenery.

Cottage in Cornwall

4.93 out of 5 average rating, 148 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Guest favorite

A serene view of Long Meadow Pond is presented, bordered by sandy areas and lush trees. The calm waters reflect the bright blue sky and distant foliage, offering a tranquil setting for outdoor activities. The scene captures a peaceful lake environment ideal for swimming and kayaking.

Cottage in Bethlehem

4.98 out of 5 average rating, 101 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Top guest favorite

A view of the bungalow from the garden, showcasing a well-maintained lawn. A swing with potted flowers hangs from a tree branch, while a stone pathway leads to the entrance. The exterior of the bungalow features a mix of windows and a porch with steps.

Bungalow in Hurleyville

5 out of 5 average rating, 134 reviews

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

Spend some time in a classic Catskill Bungalow! Beautifully renovated and nestled in the quiet yet all-inclusive Hamlet of Hurleyville; this clean space offers a great place to rest your head and bones. In the cooler months enjoy a beverage by the fireplace or in the warmer months have one on the porch and look out at all the green there is around. Walk to town for dinner, shopping, or a movie at the PAC (VisitHurleyville.org). Please see below for more information on our pet policy.

Top guest favorite

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.

Apartment in Cornwall-on-Hudson

4.98 out of 5 average rating, 214 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.

Top guest favorite

A wooden deck extends beside the house, featuring potted plants with vibrant greenery. Bicycles are parked nearby, and steps lead up to the entrance. The surrounding trees add to the serene outdoor environment.

Cabin in New Paltz

4.97 out of 5 average rating, 151 reviews

New Paltz dog friendly retreat w/salt water POOL

New Paltz dog friendly retreat is a wonderful place to explore the Hudson Valley. 7min drive to downtown New Paltz. 10min to Minnewaska state park & Mohonk preserve. Our very large fenced yard & heated 27ft salt water pool is for your private use during your stay. A signed pool waiver will be required. Heating pool fee is $20 daily. Dog fee $100 per dog. Carolyn whom lives on site in a completely separate studio is there to trouble shoot any issues & keep the pool sparkling clean.

Superhost

A serene backyard is surrounded by tall trees adorned with vibrant autumn leaves. A small shed stands along a brick pathway, flanked by neatly trimmed shrubs and an evergreen tree. The scene captures the peacefulness of nature during the fall season.

Home in Monroe

4.85 out of 5 average rating, 144 reviews

Winter Home near Legoland, West Point & Outlet

Great cozy getaway for your family near West Point, Legoland and Shopping. You have full access to the entire property. The upstairs portion includes three bedrooms, bath, kitchen and living room. TV with access to Netflix and other apps is in the living room and another television with access to Netflix in two of the bedrooms. The downstairs portion includes a private bath as well as access to a Peloton bike, elliptical, washer&dryer & pull out sofa bed.

Guest favorite

This exterior view showcases a modern two-story cabin surrounded by trees. An expansive deck features comfortable seating and a hot tub, while a stone chimney accents the home. Warm lights outline the deck, creating a welcoming ambiance at dusk.

Home in High Falls

4.94 out of 5 average rating, 127 reviews

Mossybrook Hideout: Private Creek Oasis w Hot Tub

Welcome to your High Falls getaway: a dog-friendly 3bd/3bath home complete with a hot tub, outdoor shower, chef's kitchen, wood stove, fire pit, and propane grill for entertaining your friends and family. Sonos Bluetooth speakers are provided throughout the house, a Smart TV with all of your favorite streaming apps, a large collection of board games, and laundry facilities are all available for you to use during your stay.

Superhost

A cozy reading nook is featured, with a leather armchair adorned with a soft white fur throw. A vintage-style lamp stands beside the chair, illuminating the space. A colorful area rug lies underneath, adding warmth to the neutral-toned room.

Cottage in Kerhonkson

4.9 out of 5 average rating, 183 reviews

*spring-ready* Pet-friendly private cabin!

Welcome to the Cherrytown Cottage. This cozy mid-century modern bungalow in the woods is the perfect home for a solo traveler, a couple friends, a couple, or a small family looking for a comfortable stay that’s conveniently located to some of the region's best hikes AND some of the most popular restaurants, orchards, and breweries in the area! (Or simply stay cozied up at home and play board games by the fireplace!)

Guest favorite

A peaceful farmhouse is set amidst lush greenery, featuring a stone pathway leading to the entrance. Tall trees provide a natural backdrop, and sunlight filters through the branches, creating a serene outdoor atmosphere.

Home in Napanoch

4.92 out of 5 average rating, 103 reviews

400Mbp | Firepit | Fireplace | Power Backup

Relax with the whole family at this peaceful place to stay. Super private, pet-friendly farmhouse, 2 hours from NYC in Catskills. ✔ Backyard w/ firepit ✔ Dogs allowed** ✔ 400Mbps Wifi ✔ 50” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Baseboard heating + Window Acs ✔ Onsite parking 20 mins → Minnewaska State Park 30 mins → Mohonk Preserve