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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

Guest favorite
The entrance to the private suite features a wooden deck leading to a purple door. Large windows on either side allow natural light to illuminate the entryway. Surrounding greenery and a gravel pathway create a welcoming approach to the suite.
Home in Feeding Hills
4.89 out of 5 average rating, 974 reviews

Farm Fresh Feeding Hills

MichaelRating, 5 stars2 weeks ago
This was our second stay and again it was a very pleasant experience. Mornings are beautiful as the sun lights up farm and the hillside. The sounds of the animals are soothing to the soul. We hope to stay again on our next visit.
Guest favorite
A bright bedroom features a spacious bed adorned with a blue plaid blanket. Two windows allow natural light to illuminate the room, complemented by matching bedside lamps on either side. A round mirror hangs on the wall, enhancing the room's open feel.
Home in Middletown
4.96 out of 5 average rating, 24 reviews

Middletown Loft

EdRating, 5 stars2 weeks ago
Booked this property for Wesleyan Reunion/Commencement weekend. Was well worth it to stay in a clean, comfortable, and totally private space. All instructions were totally clear and David was very accommodating. Would totally stay here again for future visits!
Top guest favorite
Home in North Haven
5 out of 5 average rating, 144 reviews

Luxury Stay in Expansive Historical Home

Rebecca Rating, 5 stars1 week ago
The house was wonderful! We stayed for my daughter’s graduation and it couldn’t have been more perfect. The special touches like having the kitchen so well stocked and toiletries in all of the rooms was especially nice, and the house had plenty of room for everyone to relax and spread out. We thoroughly enjoyed our stay!
Guest favorite
A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.
Home in South Windsor
4.9 out of 5 average rating, 147 reviews

Spacious 3 Bedroom Ranch With Office

AbbyRating, 5 stars1 week ago
We had a great stay while in town for a family wedding. The house had everything we needed for our family, which included two toddlers and a dog. The deck was a great feature and they even had extras for pets (like a dog bed) at the home. Would recommend!
Superhost
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.79 out of 5 average rating, 125 reviews

The Dragon Fly Garden

DeannaRating, 5 stars3 weeks ago
We had a marvelous stay with our friends and dogs. The location and grounds were perfect for getting to our daytime event and the Dragonfly Garden was serene for relaxing in the evening enjoying tasty delivered dinners. Thanks, Todd. We will definitely stay there again when we are in the area!
Guest favorite
The cottage exterior is framed by lush greenery, featuring a welcoming entrance with a white door accented by a wreath. Blue hydrangeas bloom in pots beside the steps, leading to a stone pathway that invites guests to explore the property.
Home in East Hampton
4.94 out of 5 average rating, 17 reviews

Lake House, Pet-Friendly

KivieRating, 5 stars2 weeks ago
My wife, friends, and I had an awesome time, and Thomas is very thoughtful. Second time renting from him, and last time I mentioned we made smores. For my wife, it was her first time. Guess what? He left us a smores kit! Thanks again, Thomas!
Guest favorite
A vibrant backyard features a spacious pool with clear blue water, complemented by a wooden deck and a shaded seating area under an umbrella. The two-story house stands in the background, surrounded by greenery, creating a peaceful outdoor environment.
Home in Montville
4.95 out of 5 average rating, 151 reviews

Casino Stay & Play House

NurisRating, 5 stars1 week ago
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you
Top guest favorite
A serene view of the Long Island Sound showcases several sailboats gently drifting on the blue water. The scene is framed by a simple fence and grassy area, with a clear blue sky above, creating a peaceful coastal atmosphere.
Home in New Haven
4.98 out of 5 average rating, 174 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

LaurrenRating, 5 stars1 week ago
Cannot say enough good things about this charming home! The house had beautiful bay windows with a spectacular view, large bedrooms with plenty of room, and was very clean. Directly across the street was a waterfront park with trails along the coastline that were a blast to explore. And it was close to everything. Highly recommend!

Pet-friendly home rentals with a pool

Guest favorite
A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.
Guesthouse in Southbury
4.93 out of 5 average rating, 322 reviews

Charming Guest Cottage with Modern Amenities

YelizaRating, 5 stars1 week ago
This place is absolutely gorgeous. I spent quite a bit of time just exploring the grounds with my dog. It was too cold to use the pool but it was still beautiful to look at and a nice view while I was cooking/washing dishes. I appreciate the tour I received when I arrived to show me around. I would definitely recommend this place and hope to book again in the future.
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 stars9 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
A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars3 weeks ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them 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, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favorite
An above-ground swimming pool is featured in a spacious outdoor area, surrounded by a wooden deck adorned with colorful lounge furniture. Lush greenery provides a tranquil backdrop, enhancing the peaceful rural setting. A paved patio offers additional outdoor space for relaxation.
Guest suite in Brooklyn
4.93 out of 5 average rating, 189 reviews

Affordable In-Law Apartment in Brooklyn, CT

KathyRating, 5 stars1 month ago
We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.
Guest favorite
A clear blue pool is surrounded by a stone patio, featuring colorful floatation devices in the water. A diving board extends over the edge, while lounge seating and cabana beds are visible in the background. The pool area is enclosed by a white fence.
Apartment in Burlington
4.85 out of 5 average rating, 110 reviews

Charming apartment with breathtaking view!

AshleyRating, 5 stars2 weeks ago
Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!
Guest favorite
The exterior of a cottage is presented, featuring natural wood siding and a gabled roof. A solid front door is centered, with a small overhang extending above. A stone pathway leads to the entrance, framed by well-maintained landscaping and grass.
Cottage in Montauk
4.91 out of 5 average rating, 598 reviews

Montauk Oceanview

SusanRating, 5 stars3 weeks ago
Always love staying at Ron’s. It’s so peaceful. Perfect location and beautiful Ocean views with a short ride if you need to go to town. Montauk Music Fest is a must. Amazing talent and great way to see all Montauk venues. Ron so great to have as a host!
Guest favorite
A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.
Home in East Hampton
4.93 out of 5 average rating, 153 reviews

Large heated pool, games room, near private beach

KarlaRating, 5 stars1 week ago
A beautiful house to always spend time with important people.

Private, pet-friendly home rentals

Guest favorite
An aerial view of the farm showcases expansive green grounds interspersed with tree cover and pathways. Several fenced areas and horse barns are visible, along with well-maintained fields. The surrounding nature creates a serene environment, inviting a sense of peace and relaxation.
Apartment in Killingworth
4.89 out of 5 average rating, 47 reviews

Life on the Farm

BrooklynRating, 5 stars1 week ago
We loved our stay here for when we visited New Haven! The place was clean and worked perfect for our dog! We loved the farm outside and the peaceful and private area outside. Would stay here again!
Guest favorite
A spacious living area features a light-colored sectional sofa with various decorative pillows. A circular coffee table sits on a patterned area rug, accompanied by a small potted plant. The sloped ceiling adds to the room's unique character, with soft lighting creating a warm environment.
Apartment in East Rock
4.97 out of 5 average rating, 29 reviews

Cozy East Rock apartment

JanetRating, 5 stars2 weeks ago
Immaculate space. Comfy couch and bed. Soft linens. Easy check in. Nice, historic neighborhood. Highly recommend!
Top guest favorite
A spacious living area features a large sectional sofa adorned with red cushions, complemented by a coffee table and side tables. Bright light floods the room through the sliding glass doors, opening to the outdoor deck. A staircase leads to a lofted area, enhancing the open feel.
Apartment in Guilford
4.96 out of 5 average rating, 83 reviews

Cozy Private Lake Q Retreat

JenniferRating, 5 stars2 weeks ago
Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.
Top guest favorite
The exterior of a two-story house is illuminated at night, showcasing modern architectural features. Large windows allow warm light to spill outside, and two outdoor chairs are positioned on the lawn, providing a welcoming space. Nearby vehicles are parked on the driveway.
Guest suite in Northford
5 out of 5 average rating, 43 reviews

Private Bright Studio Retreat with kitchen

ChuksRating, 5 stars2 weeks ago
This place is one I highly recommend when visiting this area. Everything was amazing and the host is very respectful of the space. I will definitely be booking this place again.
Top guest favorite
A two-story cottage is visible in the background, with a cozy gazebo covering a private hot tub on a red deck in the foreground. A warm sunset casts a golden hue over the scene, illuminating the surrounding trees and the inviting exterior of the cottage.
Cottage in Plymouth
5 out of 5 average rating, 19 reviews

Lakefront Summer Escape | Cool Tub | Fire Pit

AllysonRating, 5 stars1 week ago
Absolutely stunning views and peaceful vibes at this sweet cottage!!! Totally exceeded my expectations. Book now or you’ll regret it!!!
Guest favorite
A scenic driveway is framed by mature trees showcasing autumn foliage in shades of orange and yellow. The gravel path winds through a well-maintained grassy area, leading towards a serene landscape highlighted by a mix of evergreen and deciduous trees.
Guesthouse in East Hampton
4.84 out of 5 average rating, 56 reviews

Your Own Barn Loft Suite Among the Treetops

ChristineRating, 5 stars2 months ago
This is a fabulous place to stay! Beautifully decorated and all the comforts of home. Andrew and Jessica were gracious hosts and great communicators. We will definitely stay again!
Guest favorite
A combined living and dining area features a dark wood dining table with white chairs and a vase of flowers. A comfortable sofa sits alongside a light armchair, with a standing lamp providing soft illumination. Natural light filters through a nearby window.
Guest suite in Glastonbury
4.81 out of 5 average rating, 98 reviews

The Hospitable Homestead-Kid Friendly & Pets too!

AprilRating, 5 stars1 week ago
Leah’s place was perfect for our little family… we needed a place to stay with our 3 dogs while we refinished the flooring at our house. We love Glastonbury and were excited to stay for a few days. The house was close to the highway to get to work but still had a country feel. The dead end street made it feel safe to walk our dogs. The house was clean and had everything we needed to be comfy while away from home. There were a few things marked to be renovated while we were there however, it didn’t affect our stay. Leah was so responsive and sweet to our family. I would definitely stay there again!
Top guest favorite
A spacious outdoor area features a private dock along the lake, with multiple lounge chairs positioned for relaxation. Lush greenery surrounds the well-maintained yard, and a series of steps leads to the cabin. Soft lighting enhances the serene environment at dusk.
Cabin in East Haddam
5 out of 5 average rating, 18 reviews

Lakeshore Cabin with boat dock

IrenaRating, 5 stars3 weeks ago
We spent a long weekend at Dennis’ place and it was nothing short of amazing. Our aim was to relax and enjoy the lake, and we did just that. The house was exactly as described, matched and exceeded our expectations; furnished and the kitchen had everything we needed and more. If we’re back in CT, we won’t hesitate to book the house again! Thanks for being wonderful hosts!

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$6,274 GYD 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

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