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Pet-friendly vacation rentals in Middlesex County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Middlesex County

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, 271 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.

Cottage in Guilford

4.93 out of 5 average rating, 263 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Cottage in Westbrook

4.88 out of 5 average rating, 125 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, 152 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, 611 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.*

Guesthouse in Portland

4.99 out of 5 average rating, 146 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.

Rental unit in Old Saybrook

4.97 out of 5 average rating, 119 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Cottage in Middlefield

4.92 out of 5 average rating, 243 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.

Barn in Essex

4.97 out of 5 average rating, 138 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Loft in Essex

4.94 out of 5 average rating, 427 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Rental unit in Middletown

4.82 out of 5 average rating, 152 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.

Cottage in Madison

5 out of 5 average rating, 102 reviews

Shabby Chic Retreat

NOVEMBER SPC’L - Mon thru Thru $200/night. Fri -Sun $250/night. Thinking ahead…the shoreline towns are great for magical Christmas experiences and unique boutique shopping. When in CT we stay in the studio apt on the lower level of the cottage. It has a separate entrance. PLEASE NOTE: The pet fee is $25/night, per pet (not per stay)

Vacation rentals for every style

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Apartments

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A space thats all yours, with room for everyone

Popular amenities for Middlesex County pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Old Lyme

4.98 out of 5 average rating, 55 reviews

Relax & Rejuvenate in this 1920s Riverfront Estate

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in Westbrook

4.94 out of 5 average rating, 17 reviews

Barnacle Bay Beach House

Home in Clinton

5 out of 5 average rating, 4 reviews

Boulder Lake House Retreat

Home in East Hampton

4.89 out of 5 average rating, 37 reviews

A Relaxing Getaway Lake House

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

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

Home in Clinton

4.96 out of 5 average rating, 113 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Home in East Hampton

4.98 out of 5 average rating, 60 reviews

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

Pet-friendly home rentals with a pool

Home in Sag Harbor

4.81 out of 5 average rating, 133 reviews

Halloween / Autumn special - Sag Harbor Gem

Home in Cheshire

5 out of 5 average rating, 126 reviews

Pool House

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Home in Manorville

4.98 out of 5 average rating, 241 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Bungalow in Montauk

4.9 out of 5 average rating, 570 reviews

Montauk Oceanview with Fireplace (2)

Home in Cutchogue

4.98 out of 5 average rating, 125 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Home in Southampton

4.92 out of 5 average rating, 110 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Home in Southampton

4.95 out of 5 average rating, 148 reviews

Waterview, Dogs StayFree! Kayaks, Ping-Pong

Private, pet-friendly home rentals

Barn in Madison

4.96 out of 5 average rating, 46 reviews

Cozy Restored barn near beaches

Guesthouse in Chester

5 out of 5 average rating, 58 reviews

Delightful Cottage in Charming Chester

Rental unit in Middletown

4.84 out of 5 average rating, 19 reviews

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

Guesthouse in Essex

5 out of 5 average rating, 34 reviews

Adorable 2 bedroom guesthouse in Essex village

Rental unit in Deep River

4.63 out of 5 average rating, 46 reviews

Flat on the River

Guesthouse in Guilford

4.99 out of 5 average rating, 81 reviews

Page Guest House

Home in Northford

4.91 out of 5 average rating, 32 reviews

Japanese mid -century home w/ Hot Tub

Rental unit in East Hampton

4.72 out of 5 average rating, 18 reviews

Village Studio Suite

Destinations to explore