
Pet-friendly holiday rentals in Middletown
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Top-rated pet-friendly home rentals in Middletown
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Popular amenities for Middletown pet-friendly home rentals
Pet-friendly house rentals

The Gait House at High Gait Farm
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!

Cabin Love at the Lake
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

4BR House- Central Location
Caroline was a wonderful host. We felt very welcome and appreciated the breakfast food, milk, and juice. I would definitely stay there again.

Cape on the Water
We had a wonderful stay at this beautiful home. Everything was just perfect – from the clean and cozy space to the peaceful surroundings. You can tell how much care and thought went into making guests feel welcome. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and charming place to stay.

Clean/Spacious 1 bedroom house. Kitchen, LR, DR.
Where do we start? Communication leading up to and during our stay was wonderful! Anything you could possibly need was readily available, down to the jerk sauce in the fridge. Lol. We always purchase our own cleaning products anywhere we stay and this was the 1st time we used none of it. Down to cups and even the beverages left for us. The home was so welcoming and comfortable that we slept longer than we intended to and missed an activity we planned for. Lol. This was a spectacular AirBNB experience! We honestly couldn’t have asked for more. A 10/10 experience by far.

Cozy Farmhouse Retreat in North Fork, NY
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!

The Magnolia House, a Magical Vacation Rental in Mystic CT
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!

Upland Meadow Retreat - 3 bedrooms/2 baths
Madeline was easily accessible and the well-stocked house was snug, warm, and comfortable during our stay in very wintry weather. The setting is quiet, but very close to town and all amenities. We had a thoroughly enjoyable stay.
Pet-friendly home rentals with a pool

Private & Pristine with Pool and Kid’s Playard
We had a great stay. Comfortable house with a big yard and pool. Located close to EH village and also the Springs bay beaches.

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

Pool House
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

Modern East Hampton Home w/ Heated Saltwater Pool
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Charming apartment with breathtaking view!
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.

Montauk Oceanview Studio 6
This place is amazing. The beach is a 3 minute walk through the dunes. The beach itself is in an area with less density. The space of the studio itself is bigger than comes through in the photos with high ceilings and perfect set up for a peaceful and relaxing beach get-away. Comfortable bed.

Explore the Water & Woods at a Relaxing Retreat
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
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

Total Privacy in Springs.
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.

Peaceful and Private 3 bedroom home in the woods
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!

Modern cozy, pet friendly
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!

Twin Pond Ocean View 2 Bedroom #4
We come to Montauk often & loved this spot. Walkable & convenient to town plus a beach pass. The accommodation had plenty of space for a family with convenient parking. Highly recommend!

Private and Serene home close to I-84 and shopping
We were looking for a last minute peaceful four day getaway and we found it here. We can’t stop talking about it. Although relatively close to everything we felt as if we were in the middle of a forest. The only sounds were the chirping of song birds and a woodpecker in the morning. Local restaurants are great and for us a trip to Yale University’s free museums and nearby antique shops rounded things out. The house is charming and Rio, our host , made sure we had everything. The few things we forgot from home were there! Wonderful experience all around.

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

Southold- Adorable 1 Bedroom Cottage
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.

Serene Waterfront Cottage
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.
Quick stats about holiday rentals that are pet-friendly in Middletown
Total rentals
30 properties
Nightly prices starting at
$47 AUD 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
Wi-Fi availability
30 properties include access to Wi-Fi
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- Beach
- Misquamicut State Beach
- Fairfield Beach
- Hammonasset Beach
- Ocean Beach
- Yale University
- Pleasure Beach
- Soundview Beach
- Watch Hill Beach Association Beach
- Dunes Park Beach
- Rocky Neck State Park Bathing Beach
- Stony Creek Beach
- Weekapaug Inn Beach
- Sea Bluff Beach
- Foxwoods Resort Casino
- Limewood Beach
- Esker Point Beach
- Maidstone Park Beach
- Halsey Neck Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Six Flags New England
- Quotonset Beach
- Walnut Public Beach