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Pet-friendly vacation 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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Rental unit in East Haddam

4.78 out of 5 average rating, 274 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guesthouse in Southbury

4.94 out of 5 average rating, 309 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).

Home in North Haven

5 out of 5 average rating, 134 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Cottage in Westbrook

4.88 out of 5 average rating, 127 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Home in East Haddam

4.94 out of 5 average rating, 157 reviews

Romantic Getaway at The Lake!

Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located, 30 minutes from Hartford, 30 minutes from the Mohegan Casino.

Cabin in East Haddam

4.89 out of 5 average rating, 627 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.*

Cottage in Hebron

4.89 out of 5 average rating, 113 reviews

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

Guesthouse in Portland

4.99 out of 5 average rating, 149 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Home in Bristol

4.91 out of 5 average rating, 150 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.

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.

Rental unit in Middletown

4.82 out of 5 average rating, 154 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.

Home in Cheshire

5 out of 5 average rating, 128 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

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Popular amenities for Middletown pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in South Windsor

4.92 out of 5 average rating, 124 reviews

Spacious 3 Bedroom Ranch With Office

Home in Woodbury

4.99 out of 5 average rating, 121 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Home in East Lyme

4.97 out of 5 average rating, 122 reviews

Walk to the beach at Black Point, Niantic, Ct

Home in Mansfield

4.88 out of 5 average rating, 24 reviews

Stunning Mansfield Getaway near UConn & ECSU

Home in Bloomfield

4.95 out of 5 average rating, 109 reviews

Spacious Charming New England Cape

Home in New Haven

4.97 out of 5 average rating, 159 reviews

WaterviewsTakeWedding pics,CollegeTours Yale&Beach

Home in Simsbury

4.98 out of 5 average rating, 106 reviews

Nature House, water view, gazebo. 2 large decks

Pet-friendly home rentals with a pool

Home in Simsbury

5 out of 5 average rating, 11 reviews

An Oasis Where Nature & Comfort Unite

Villa in Killingworth

5 out of 5 average rating, 14 reviews

1-of-a-kind Estate w/ Pool, Spa, Tennis & Pond

Guesthouse in Rocky Hill

4.92 out of 5 average rating, 13 reviews

Camellia Springs - Solace & Rest

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Rental unit in Burlington

4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

Home in Bethlehem

5 out of 5 average rating, 34 reviews

Lakeview Expanse

Home in Montville

4.95 out of 5 average rating, 128 reviews

Casino Stay & Play House

Home in Litchfield

4.93 out of 5 average rating, 177 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Private, pet-friendly home rentals

Rental unit in Killingworth

4.88 out of 5 average rating, 33 reviews

Life on the Farm

Rental unit in Manchester

4.98 out of 5 average rating, 41 reviews

Cozy 1 bedroom clean and quiet

Guest suite in Northford

5 out of 5 average rating, 29 reviews

Private Bright Studio Retreat with kitchen

Home in East Hampton

4.98 out of 5 average rating, 60 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

Cottage in Windsor

4.9 out of 5 average rating, 172 reviews

In-law apartment in Farmington River Cottage

Guesthouse in East Hampton

4.87 out of 5 average rating, 52 reviews

Your Own Barn Loft Suite Among the Treetops

Rental unit in Middletown

4.85 out of 5 average rating, 20 reviews

Cozy 2BR/1BA Apt | 5 Mins from Wesleyan & CT River

Guest suite in Glastonbury

4.79 out of 5 average rating, 89 reviews

The Hospitable Homestead-Kid Friendly & Pets too!

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

Total rentals
30 properties
Nightly prices starting at
R725 ZAR 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