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

Guesthouse in Southbury

4.93 out of 5 average rating, 314 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).

Guest favourite

Home in Old Saybrook

4.97 out of 5 average rating, 119 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Guest favourite

Home in Bloomfield

4.95 out of 5 average rating, 111 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods near Wintonbury Hills Golf course. Neighborhood setting and on a private corner lot. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails too! Close to Ski Sundown, Mt Tom, MGM Casino, tons of golf courses, beaches.

Superhost

Cottage in Branford

4.86 out of 5 average rating, 222 reviews

Cozy Home In Short Beach Community

A cozy home in a beach community which is in a central location with easy access to many outdoor activities(private beach access) & local restaurants. The location is also 5 minutes from the Branford Train Station, Stony Creek Brewery, Branford's town center. New Haven the home of Yale University, Yale Hospital and other colleges in the New Haven area are a short drive The house is across the street from Farm River. across the street in opposite direction is a short walk to Johnsons beach.

Superhost

Cabin in East Haddam

4.89 out of 5 average rating, 660 reviews

Postcard Cabins Machimoodus - NYC/Boston

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favourite

Cottage in Plymouth

4.95 out of 5 average rating, 100 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

Come stay @cozyoasisct for sunset hour and enjoy dramatic views from the comfort of the living room, kitchen, or outdoor patio. Our private community lake is great for swimming, fishing, kayaking, bird watching and ice skating in the winter. Great for your next getaway, relaxing weekend, or just a place to work remotely. The property is equipped with kayaks, shuffleboard, fast WiFi, deskspace, Smart TVs, and a full kitchen. We can’t wait to host you! We're Pet Friendly

Guest favourite

Home in Winsted

4.99 out of 5 average rating, 110 reviews

Cheerful 2 Bedroom Home at Highland Lake

Welcome to the Uncorked Cottage, a fun and relaxing space for you and your family to retreat to. Comfort meets style in this updated home with a cozy remote gas fireplace, 55” smart TV and high speed WiFi. The kitchen is fully equipped cook up your favorite recipes. Located across the street from Highland lake and walking distance to Resha Beach. Just minutes from downtown where you’ll find restaurants and activities for all. Just a short drive to ski mountains.

Guest favourite

Home in Bristol

4.92 out of 5 average rating, 156 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Guest favourite

Cottage in Middlefield

4.92 out of 5 average rating, 244 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Guest favourite

Cabin in Coventry

4.86 out of 5 average rating, 154 reviews

Guest favourite

Home in Litchfield

4.98 out of 5 average rating, 228 reviews

Storybook Cape...HOST & Co.

A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where you can enjoy antiquing, dining, shopping, and relaxing in the picturesque town center. If hiking and outdoor activities are more your thing we are also minutes from White Memorial Foundation and Topsmead National Forest is right around the corner. Mohawk Mountain Ski Area is 12 miles away.

Guest favourite

Tiny home in East Lyme

5 out of 5 average rating, 122 reviews

Luxury Tiny Home Near Rocky Neck

Home away from home at our chic hideaway! Create a culinary masterpiece in the fully-appointed kitchen. Pamper yourself with heated floors in the bathroom, outdoor fire pit and heater. An elevated platform perfect for camping or yoga. Nestled just minutes from the picturesque Rocky Neck and McCooks beach, this is the ultimate small family romantic retreat or solo experience!