Pet-friendly holiday rentals in Middletown

Find and book unique pet-friendly homes on Airbnb

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 favourite

Home in East Stroudsburg

4.97 out of 5 average rating, 170 reviews

Dog Friendly🐶 Lakefront🎣 Hot Tub🔥 Newly Renovated🤩

This newly renovated 3000 sqft lakefront property features close to 1000 sqft of lakefront decking/patio space, ample driveway parking for guests, direct lake access for kayaking or fishing, a BBQ grill, hammocks, 6 person hot tub, & much more! The ground floor features 2 bedrooms, a full bath, family room, game room, & laundry area. The 2nd FL has a full kitchen, 4 bedrooms, living & dining rooms and 2 full baths. The house has central air heating & cooling. FREE access to community amenities!

Top guest favourite

Cottage in Roscoe

4.98 out of 5 average rating, 103 reviews

Roscoe Cottage Pet Friendly

Welcome to Roscoe, Trout Town USA! Escape 2 the mountains with your family & pets 4 a rustic getaway. At Roscoe Cabin Pet Friendly, we provide a complimentary bottle of wine with your booking. Enjoy strong WiFi, big fire pit, bbq & a stocked kitchen. Our property is nestled in the woods at the top of the mountain very peaceful offering access hundreds of trails, lakes, and brooks for endless adventures. Only 14 miles to Bethel Woods Concert Venue. We look forward 2 hosting you & your 🐶soon!

Top guest favourite

Home in Coolbaugh Township

4.97 out of 5 average rating, 144 reviews

Lakefront retreat w/rowboat & suana. Dogs allowed.

Lakefront retreat in the Poconos with Boat & Sauna! Dog-friendly. - Spacious 3BR/2BA home with stunning views of Pocono Summit Lake. - Dog-friendly and conveniently located near popular attractions like Kalahari, Camelback, Jack Frost, Mt. Airy Casino, grocery and the Outlets. - Relax and enjoy the beauty of the Poconos on the deck overlooking the lake. - Enjoy all the watersports and fishing the lake has to offer with rowboat, electric motor, 2 kayaks, paddleboard, firepit and charcoal grill.

Guest favourite

Home in Saugerties

4.87 out of 5 average rating, 126 reviews

Le Petit Cottage - French Country in Saugerties

Le Petit Cottage is a cozy renovated farmhouse retreat in the heart of the scenic Hudson Valley, located 2 hours from NYC, Saugerties, NY Set on a spacious corner lot across from a waterfall, the house has gorgeous mountain views, with 3 bedrooms and 2 baths, and comfortably sleeps 6 people. The house features a high-end kitchen, a wood-burning stove, and luxurious amenities. This property is extremely dog-friendly! Centrally located to Woodstock, Kingston, and under 25 minutes to Hunter Mtn.

Superhost

Home in East Stroudsburg

4.84 out of 5 average rating, 102 reviews

Waterfront, Mountain Views, Dog Friendly, Fire Pit

Escape to your private waterfront retreat, where breathtaking mountain views and tranquil surroundings await. Unwind in comfort with a plush king bed, perfect for restful nights, and enjoy peaceful evenings by the fire pit. This secluded, dog-friendly haven offers direct access to the river, ideal for outdoor exploration or quiet reflection. Whether you're seeking relaxation or adventure, this serene paradise is your perfect getaway. Book now for an unforgettable experience in nature’s embrace!

Superhost

Home in Lake Ariel

4.87 out of 5 average rating, 129 reviews

Lakeview Chalet - Pool & Lake/Beach - Kayaking

Perfect getaway with lake views. Large deck, BBQ & fire pit in a safe family-friendly community with lots of amenities! Steps away from the pool - close to beach/lake area. HOME HAS AIR CONDITIONING and Fans! Community has 2 Lakes and pools with beach/BBQ area. All you need for a fun-filled and relaxing getaway. Basketball & Tennis Courts, Kayak rentals and more... Winter -The Hideout offers snow tubing and skiing. Guests are responsible for lift tickets, rentals and any other fees for use.

Superhost

Cottage in Shohola

4.83 out of 5 average rating, 153 reviews

Modern Forest Retreat on a Tranquil HilltopSAUNA

Tucked away on the hilltop, overlooking tall pine trees and beautiful forest - Shohola Cottage welcomes you. And you will want to stay. For a while :-) Enjoy exceptional comfort of this house. Every detail of interior was created with thoughts of You, our guests, our friends and our family. To give you unforgettable experience. Exceptional Interior Design , Comfortable Couches, Inviting Dining Table ,Wrap around Terrace , Fireplace and Fire Pit. Lots of Sunlight and Air. Crispy Clean Air.

Superhost

Cottage in Tobyhanna

4.92 out of 5 average rating, 164 reviews

Lakefront-w/ PRIVATE HOT TUB-near all Attractions!

Welcome to our Pocono Mountain Lakefront home. We are located in the heart of the Poconos, in a full amenity, secure gated community. Our cozy-waterfront home has everything you need for a relaxing stay in the Pocono Mountains. Our modern lake house is the perfect retreat for families and friends, offering 4 seasons of fun where you’ll create endless memories. We want you to feel relaxed while you are here, so we have made every effort to ensure your comfort during your stay!

Guest favourite

Chalet in Stroudsburg

4.95 out of 5 average rating, 422 reviews

Dog-Friendly Chalet in the Heart of the Poconos

This comfortable home with a fully fenced yard is located in the heart of the Pocono Mountains. It is minutes from Camelback Mountain, The Crossings Premium Outlets, the Pocono Raceway, indoor and outdoor water parks, the Appalachian Trail, and some of Pennsylvania's best fishing and hunting. The property features a 1/3 acre fully fenced yard with deck access including a smaller fenced area for letting dogs out in a more contained space than the larger fenced yard.

Guest favourite

Home in Palenville

4.96 out of 5 average rating, 164 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Superhost

Cottage in Kerhonkson

4.91 out of 5 average rating, 182 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!)

Top guest favourite

Home in Saugerties

4.99 out of 5 average rating, 142 reviews

Saugerties Village Retreat

Charming Village home located 5 minutes from Hits. Walking distance to village restaurants & shopping. Front porch, Private backyard with deck and patio. Large eat in kitchen with separate dining room. Spacious Living room with 2 couches and daybed. Cable TV & Wifi Driveway & street parking for up to 3 cars. washer, dryer, dishwasher . Fully fenced in yard for up to 2 dogs with pre approval from host.