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Pet-friendly vacation rentals in Middletown

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Middletown pet-friendly home rentals

Pet-friendly house rentals

Superhost
The exterior of the house features a two-story white façade with brown accents. A patio area includes a table and several chairs, alongside lounge chairs arranged on green grass. A tree provides partial shade, with two propane tanks visible on the side.
Home in North Branford
4.86 out of 5 average rating, 7 reviews

The Gait House at High Gait Farm

DaveRating, 5 stars6 days ago
We had to find a place last minute due to some unexpected circumstances, and Lori was incredibly accommodating. We only needed it for one night to fit five of us, and the three-bedroom setup was perfect. She went above and beyond by offering early check-in and late check-out, and even brought us muffins and coffee since she knew we had to hit the road early. The space was cozy, clean, and very comfortable. The Wi-Fi was a little spotty at times, but it didn’t cause any major issues. All in all, a great stay — we’ll definitely be back next time we’re in town!
Superhost
Home in Milford
4.84 out of 5 average rating, 55 reviews

Charming 2BR Home | Fast Wi-Fi & Outdoor Space

LindaRating, 5 stars3 months ago
Ritestay was a great place. We didn’t spend much time there because we were there to see our daughter. Would be perfect in the summer!!
Superhost
A red home is visible among the trees, surrounded by lush greenery. In the foreground, a hammock is strung between two trees. Bright red outdoor seating is seen on the patio, inviting relaxation in the natural setting.
Home in Coventry
4.73 out of 5 average rating, 40 reviews

Cabin Love at the Lake

JonRating, 5 stars2 months ago
I appreciated all the snacks and drinks that were included. Bathroom was stocked with everything you'd need and there was detergent for the washer too
Superhost
A cozy living area features a stone fireplace with candles, complemented by a modern flat-screen TV mounted above it. A plush armchair provides seating, while windows invite natural light, showcasing a peaceful outdoor view. A small bookshelf holds various books.
Home in Manchester
4.91 out of 5 average rating, 43 reviews

4BR House- Central Location

RaghuRating, 5 stars3 months ago
It's hard to find Airbnbs that can accommodate several people in central CT. Luckily, Caroline's listing came to the rescue! Good location in a quiet Manchester suburb, close to Main Street. Nice Ikea dishware, spacious fridge. Parking (no garage), was ample. The upstairs area has low ceilings, but the beds were fine. The main living room area was cozy and full of CT-related board games and books, and several candles. The dining table gets the job done, though we threw some pillows on the dining chairs to maximize comfort. Also, the listing clearly states this, but keep in mind that there is only one bathroom. Caroline was a great communicator. All questions were promptly answered. She also extended a complementary extended checkout, which came in handy.
Guest favorite
A scenic view of Ash Creek is captured, showcasing calm waters reflecting the clouds overhead. In the foreground, a grassy yard is bordered by a wooden fence, while a small red shed is positioned to the right, providing additional storage space.
Home in Black Rock
4.96 out of 5 average rating, 85 reviews

Cape on the Water

BethRating, 5 stars3 months ago
Jim’s home is lovely and tranquil. To look at the beautiful ash creek every day with the wonderful wildlife was amazing. The inside of the home was very well appointed … excellent attention to detail in the kitchen and bathrooms. Very comfortable and cozy !!
Guest favorite
A spacious wooden deck features a picnic table shaded by a striped umbrella. A gas grill stands nearby, and comfortable seating is arranged around the space. Lush greenery surrounds the area, creating a private and serene outdoor experience.
Home in North Fork
4.91 out of 5 average rating, 104 reviews

Cozy Farmhouse Retreat in North Fork, NY

MarisaRating, 5 stars1 week ago
This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!
Top guest favorite
A single-story expanded cape home is framed by lush greenery and colorful flowering plants. Bright blue skies provide a clear backdrop, while the welcoming front door enhances the inviting exterior. The landscaped yard includes well-maintained grass and various garden features that promote relaxation.
Home in Mystic
4.99 out of 5 average rating, 89 reviews

The Magnolia House, a Magical Vacation Rental in Mystic CT

JoeyRating, 5 stars1 week ago
Our recent stay at The Magnolia House in Mystic, CT, was delightful. The home comfortably accommodated our group of five adults and one infant. Its location provided easy access to Mystic's attractions, making our visit convenient and enjoyable. We highly recommend The Magnolia House to anyone visiting the area!
Guest favorite
A cozy living area features a green sofa adorned with colorful floral cushions. A coffee table with a light-colored surface is centered on warm wooden flooring. In the background, a dining area with dark chairs is visible, alongside an archway leading to the kitchen.
Home in Longmeadow
4.96 out of 5 average rating, 80 reviews

★Unique Suburban Retreat Cozy Comfy Pet Friendly★

Kristen AnneRating, 5 stars3 months ago
I really liked staying in this Airbnb and it’s prime location in Longmeadow, Massachusetts. It was convenient to my parents home, who I was visiting. There was a polar vortex and the home was so toasty warm and cozy! I really enjoyed getting back there at the end of my day. This AirBnB is one of the better stocked properties I’ve stayed at. They had plenty of towels, sheets, extra fleece blankets, and kitchen items. Many times when I stay at a place I will run out of things such as garbage bags and paper towels, and there aren’t any extra there. That wasn’t the case at Robert’s property. He was very, very thoughtful in setting up this home for guests! I’ll be back! Thank you.

Pet-friendly home rentals with a pool

Guest favorite
The outdoor area features a spacious backyard with a patio, outdoor dining set, and a barbecue grill. The wooden exterior of the house is complemented by lush greenery and a fenced perimeter, creating a serene environment for gatherings.
Home in East Hampton
4.88 out of 5 average rating, 106 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars2 weeks ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Superhost
An outdoor swimming pool is framed by a brick patio, with lounge chairs positioned nearby. A two-story house and a separate pool house are visible in the background, surrounded by lush greenery and mature trees, creating a serene outdoor escape.
Home in East Hampton
4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

LisaRating, 5 stars8 months ago
Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Superhost
The living room features a blend of modern and mid-century design with a wood-planked ceiling. A large flat-screen TV is mounted on the wall above a wood-burning fireplace. A comfortable seating area includes a black leather couch and two orange chairs, complemented by decorative accents.
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars7 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Guest favorite
Apartment in Burlington
4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

RebeccaRating, 5 stars7 months ago
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.
Guest favorite
An open floor plan reveals a studio space with hardwood flooring and an open beam ceiling. A spacious bed is placed against one wall, complemented by a light-toned nightstand. A circular fireplace is positioned near a blue accent chair and a dining table.
Cottage in Montauk
4.92 out of 5 average rating, 263 reviews

Montauk Oceanview Studio 6

RebeccaRating, 5 stars1 week ago
Ron’s cottage was at a perfect location and easily walkable to the beach. The cottage had plenty of space and everything you could need!
Guest favorite
The exterior of a spacious house is shown, featuring multiple windows and a large enclosed porch. Lush greenery surrounds the home, with vibrant flowers in shades of pink and purple adding color. A well-maintained lawn provides ample outdoor space, complemented by stone landscaping.
Home in Litchfield
4.93 out of 5 average rating, 185 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

TessaRating, 5 stars4 days ago
This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!

Private, pet-friendly home rentals

Superhost
A wooden deck overlooks a lush garden, surrounded by tall trees. Colorful flowers are visible along the garden path, while a natural, serene landscape creates a private and peaceful environment.
Apartment in East Hampton
4.75 out of 5 average rating, 20 reviews

Total Privacy in Springs.

SylviavRating, 5 stars6 months ago
The place is roomy and clean. The bed is comfy and the shower is great. There were juices and sodas and water in the mini fridge, a coffee maker with coffee and some wrapped snacks. A comfortable place to stay in a very pricy part of Long Island if you prefer a home over a hotel. We were only there for the 2 nights of our stay since we were out all day and for that it was perfect.
Guest favorite
The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.
Home in Shelter Island
4.88 out of 5 average rating, 26 reviews

Peaceful and Private 3 bedroom home in the woods

Robert,Donald JrRating, 5 stars8 months ago
Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!
Guest favorite
A modern kitchen features sleek cabinetry and a spacious island with a stone base. Three bar stools are positioned at the island, next to stylish pendant lights. A stainless steel refrigerator and a microwave are visible, along with various kitchen essentials arranged thoughtfully on the counter.
Guest suite in Wolcott
4.93 out of 5 average rating, 56 reviews

Modern cozy, pet friendly

MelissaRating, 5 stars1 week ago
Had a wonderful time at Altin’s place - perfect for a quick overnight near my in-laws. The space was gorgeous, clean & well-appointed. Had everything we needed and more!
Guest favorite
A two-story home is nestled among trees, featuring light-colored siding and a gray roof. A red patio umbrella provides shade over a seating area in the yard, while a gravel pathway leads to the front door, enhancing the natural surroundings.
Cottage in Newtown
4.93 out of 5 average rating, 240 reviews

Private and Serene home close to I-84 and shopping

SarahRating, 5 stars2 weeks ago
Rio was a really friendly and helpful host and his cottage was very cute in a lovely area surrounded by trees and great walks and hikes. We made s'mores over the fire pit, enjoyed the quiet, and explored a few towns nearby. Great weekend!
Guest favorite
A cozy bedroom features a spacious bed with comfortable linens, complemented by a decorative bench at the foot. Warm wood tones enhance the inviting atmosphere, while a ceiling fan provides airflow. An adjacent doorway reveals the fully equipped kitchen, adding functionality to the space.
Apartment in Wallingford
5 out of 5 average rating, 22 reviews

Eclectic 2 BR, 1 Ba apt w/Free Off-Street Parking

GiovanniRating, 5 stars1 month ago
Stayed here for about a month and felt right at home with spacious rooms and lots of amenities provided, being 20 degrees in winter the apartment stood very warm and clean and it was a wonderful place to call home for 30 days. Kisha was very helpful and responsive when I needed to communicate and she’s very kind. If I’m ever near the area in the near future I would definitely book here again no hesitation! Thank you!
Guest favorite
A sunlit living area features a light-colored sofa accented with blue pillows. A coffee table sits in front, and a ceiling fan adds comfort. Large windows provide views of greenery outside, while a side table with a lamp enhances the cozy ambiance.
Guesthouse in North Fork
4.91 out of 5 average rating, 57 reviews

Southold- Adorable 1 Bedroom Cottage

VictoriaRating, 5 stars1 month ago
Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.
Guest favorite
A dog stands on a wooden dock, facing a tranquil waterway at sunrise. The still water reflects trees and a gentle glow from the rising sun, creating a serene landscape. The peaceful atmosphere is enhanced by nature's sounds.
Cottage in Deep River
4.91 out of 5 average rating, 22 reviews

Serene Waterfront Cottage

RobertRating, 5 stars4 months ago
As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.
Guest favorite
A well-maintained deck is visible, featuring outdoor seating and an umbrella for shade. Planters with colorful flowers adorn the area, while a smooth gravel path leads to the yard, surrounded by trees. The space is designed for relaxation or social gatherings.
Apartment in North Haven
4.88 out of 5 average rating, 43 reviews

Charming Dog Friendly Suite On Scenic Property

RuthanneRating, 5 stars3 months ago
Nice place located in a beautiful secluded house in a safe neighborhood. Gorgeous property. Our dogs were allowed and they were very comfortable. The amenities were exactly as described. Extremely clean and well maintained. The place was easy to locate and easy to access. It is convenient to many local stores and restaurants. Great, responsive hosts!

Quick stats about vacation rentals that are pet-friendly in Middletown

  • Total rentals

    30 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore