Pet-friendly vacation rentals in Middletown

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Top-rated pet-friendly home rentals in Middletown

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

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Guest favorite

A custom-built cabin is surrounded by trees and landscaped greenery. It features natural wooden shingles on one side and large windows that invite light. A welcoming deck is adorned with seating, and garden lighting accents the path leading to the entry, enhancing the rustic charm.

Tiny home in Montgomery

4.96 out of 5 average rating, 266 reviews

Lux Cabin on Farm, River, Animals, Smart Projector

Take a break from your day to day and enjoy this serene and unique escape. The Trek is a custom built and designed cabin nestled in the heart of the Hudson Valley! It is a high class, off-the-grid experience. Come experience the escape for your self - Watch a movie, visit the animals on the farm, read a book, roast s’mores or enjoy a night under the stars around the fire pit, how ever you like to relax do it at The Trek. Located just 3 Minutes from cafes, local restaurants, hikes and much more.

Top guest favorite

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

4.99 out of 5 average rating, 178 reviews

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Guest favorite

A private deck area features a wooden chair beside a neatly stacked pile of firewood. The entrance displays a large sliding glass door, illuminated from within, revealing a warm interior. Soft outdoor lighting complements the natural surroundings of greenery.

Tiny home in Livingston Manor

4.97 out of 5 average rating, 126 reviews

Element House - Off Grid Hideout

Unwind and reconnect with nature in this rustic and comfortable retreat nestled at the edge of a blueberry field. Surrounded by serene Catskills countryside, you’ll feel a world away, yet still be just minutes from outdoor activities, a thriving food scene, and Bethel Woods just 35 min away. Inside, you’ll stay cool with AC, a cozy queen bed, kitchenette, dining table, reliable wifi, and full bath. Outside, relax by the fire pit or cook on the charcoal grill. We are an LGBTQ+ inclusive space.

Top guest favorite

A gravel pathway leads through a forest of autumn foliage, revealing a tiny house nestled among the trees. A small black and white dog stands on the path, surrounded by fallen leaves in vibrant orange and yellow hues.

Tiny home in Wallkill

4.99 out of 5 average rating, 301 reviews

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.

Guest favorite

Feet are seen dangling over a gently flowing stream, with a snowy landscape surrounding the banks. The cabin is glimpsed in the background, its vibrant green color contrasting against the natural elements and the soft glow of early sunlight filtering through the trees.

Cabin in Vernon Valley

4.96 out of 5 average rating, 422 reviews

Serenity Cabin, the historic waterfall cabin!

Escape to a magical paradise where the sound of a babbling stream & chirping birds create a symphony of serenity. Nestled on 18 acres of pristine wilderness, this secluded retreat offers endless opportunities for exploration & adventure. Wander along the streams and discover hidden waterfalls, all while immersing yourself in the breathtaking beauty of nature. Located 5 minutes from Mountain Creek, Warwick drive-in, Appalachian trail, & activities like goat yoga, horse riding, & TreEscape adv.

Guest favorite

A golden retriever sits on a wooden dock at sunset, reflecting on the calm lake. The sky features varying hues of orange, blue, and pink, mirrored in the water's surface. Nearby trees and distant houses are softly illuminated by the fading light.

Cottage in Monroe

4.99 out of 5 average rating, 160 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Guest favorite

A charming cabin nestled among tall trees features a screened-in porch with two green chairs. A fire pit surrounded by logs and stones sits in the foreground, providing a cozy gathering space. The cabin's rustic exterior is complemented by deep-set skylights.

Cabin in Kerhonkson

4.96 out of 5 average rating, 556 reviews

Cozy Cabin - pet friendly + near hiking

Take a leisurely walk under the towering trees in the quiet wooded acre surrounding our cozy, alpine-inspired cabin with contemporary bohemian touches. Sleep in upstairs under deep-set skylights, observe wildlife out our large picture windows, or curl up by the fire on the rustic screened porch. Daydream on our hammock or dine alfresco taking advantage of our barbeque. On a clear night, it is easy to stargaze up through the tall trees, perhaps while toasting marshmallows fireside.

Guest favorite

A dining area features a handmade wooden table surrounded by four multicolored chairs. Shelving above holds books and decorative items. On the walls, a collection of framed art pieces adds character. Soft lighting illuminates the space, creating a cozy atmosphere.

Apartment in Wallkill

4.89 out of 5 average rating, 408 reviews

Dream getaway apartment in the foot of Gunks Ridge

Beautifully decorated space full of original art located in the foot of Shawangunk Ridge on the side of a large farm field and a forest. Get together with friends at the handmade farm dining table, feel hygge next to a wood-fired place, enjoy nature tranquility, and recharge. We provide ALL you need: clean towels, cooking essentials, complimentary high-end loose tea /coffee, friendly atmosphere, and good local advice. Apartment is a half basement part of a house but has full privacy.

Guest favorite

A bright living area is highlighted by a sleek black couch and a stylish coffee table at its center. Natural light fills the space through multiple windows, while a vibrant area rug and a tall plant add warmth and character to the room.

Apartment in Newburgh

4.86 out of 5 average rating, 194 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top guest favorite

An aerial view of an outdoor space reveals a rustic cabin surrounded by a carpet of fall leaves. A large wooden dining table is set with chairs, while string lights create a warm atmosphere. A hot tub and fire pit invite guests to enjoy the natural setting.

Cabin in Cuddebackville

4.99 out of 5 average rating, 136 reviews

Sauna & Hot Tub Creekfront Oasis · Hikers Hollow

Tucked away in the small town of Cuddebackville, you will find a wonderful rough cut cabin with all the comforts and amenities for a relaxing stay. The cabin is situated on 3+ acres on a quiet dead end road with very minimal car activity. Enjoy the wonderful nature that surrounds you, with the calming sound of the stream in the background. The interior of the cabin has been updated to ensure an exceptionally comfortable stay while still holding true to its original 1940's charm.

Guest favorite

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.

Home in Newburgh

4.99 out of 5 average rating, 161 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.

Top guest favorite

Cabin in Yulan

4.98 out of 5 average rating, 158 reviews

Waterfront Cozy A Frame - Enchanting River Cabin

Enchanting River is a magical 2BR 1Bath A-Frame home secluded on 4 acres of serine forest nestled beside beaver brook running right below the house. This magical get away is just 2 hours from NYC & 2.5 hours from Philly. Only 20 minutes to SKI BIG BEAR, a great snowboarding/ski mountain! As dawn turns to daybreak, there’s nothing more pleasant than being drawn from slumber by the sound of gushing water echoing through each surface of the property.