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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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Guesthouse in East Hampton

4.83 out of 5 average rating, 42 reviews

Your Own Barn Loft Suite Among the Treetops

Forget your worries in this spacious and serene space. You’ll arrive through your own driveway, park in your own spot and enter through a private entrance. Make yourself at home whether a weekend get away or traveling for work you’ll feel very relaxed. 250’ from the airline trail, walk or bike right into downtown East Hampton for a coffee in the morning or set out on the 30 + mi trail to enjoy your true country getaway. Head into Middletown to enjoy many restaurants, bars or clubs. *NOTE PET FEE

Jan 21 – 28

R3,285 ZAR per night

Guesthouse in Chester

5.0 out of 5 average rating, 41 reviews

Delightful Cottage in Charming Chester

Enjoy all the Connecticut River Valley has to offer and use this newly renovated cottage as your relaxing home base. The cottage is a 2 min. drive (or 12 min. walk) to charming downtown Chester. There you will find delicious dining options, unique shops, galleries, a brewery and a theater. Chester is also home to a wonderful Sunday farmers market -mid June to mid October. Area attractions include Gillette Castle, Essex Steam Train, Florence Griswold Museum, CT River Museum and wonderful hiking.

Oct 30 – Nov 6

R4,018 ZAR per night

Home in Chester

4.98 out of 5 average rating, 197 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

Apr 15 – 22

R6,331 ZAR per night

Yurt in Guilford

4.9 out of 5 average rating, 101 reviews

Hartwoods Yurt

Enjoy a unique, private, wilderness getaway and unwind in a peaceful wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

Jul 15 – 22

R3,939 ZAR per night

Apartment in Glastonbury

4.9 out of 5 average rating, 409 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Feb 16 – 23

R2,106 ZAR per night

Apartment in Middletown

4.98 out of 5 average rating, 150 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Sep 12 – 19

R2,389 ZAR per night

Cabin in East Haddam

4.89 out of 5 average rating, 367 reviews

Getaway Machimoodus - NYC/Boston

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Mar 31 – Apr 7

R7,189 ZAR per night

Cottage in Middlefield

4.93 out of 5 average rating, 230 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.

Apr 5 – 12

R3,186 ZAR per night

Guesthouse in Madison

5.0 out of 5 average rating, 59 reviews

The Barn by the Sound

Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

Feb 6 – 13

R3,059 ZAR per night

Barn in Essex

4.98 out of 5 average rating, 125 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.

Sep 17 – 24

R12,225 ZAR per night

Apartment in Middletown

4.81 out of 5 average rating, 132 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.

Nov 27 – Dec 4

R2,391 ZAR per night

Home in Old Lyme

4.96 out of 5 average rating, 129 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Apr 13 – 20

R7,317 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Houses

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 Saybrook

4.96 out of 5 average rating, 104 reviews

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

Mar 19 – 26

R7,052 ZAR per night

Home in Old Saybrook

4.96 out of 5 average rating, 50 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Nov 18 – 25

R3,629 ZAR per night

Home in Haddam

4.84 out of 5 average rating, 31 reviews

Tranquil Lakefront Home @ Hidden Lake

Sep 24 – Oct 1

R6,684 ZAR per night

Home in East Hampton

4.98 out of 5 average rating, 51 reviews

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

Jan 5 – 12

R5,808 ZAR per night

Home in Middletown

4.95 out of 5 average rating, 19 reviews

Hot Tub and pool Home away from home

Sep 9 – 16

R8,276 ZAR per night

Home in Chester

4.98 out of 5 average rating, 50 reviews

Tuscan Villa in Chester

Aug 6 – 13

R10,898 ZAR per night

Home in Essex

5.0 out of 5 average rating, 24 reviews

3-Bedroom Farmhouse, Essex CT

Jun 6 – 13

R8,306 ZAR per night

Home in East Hampton

4.96 out of 5 average rating, 24 reviews

A Relaxing Getaway Lake House

Sep 6 – 13

R11,231 ZAR per night

Pet-friendly home rentals with a pool

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

Nov 14 – 21

R2,668 ZAR per night

Apartment in Ledyard

4.96 out of 5 average rating, 138 reviews

Rustic Retreat (just minutes from Casinos/ Mystic)

Jan 3 – 10

R2,919 ZAR per night

Home in Montville

4.96 out of 5 average rating, 106 reviews

Casino Stay & Play House

May 31 – Jun 7

R8,626 ZAR per night

Bungalow in Montauk

4.91 out of 5 average rating, 531 reviews

Montauk Oceanview with Fireplace (2)

Dec 18 – 25

R3,719 ZAR per night

Home in Manorville

4.99 out of 5 average rating, 201 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct 18 – 25

R10,632 ZAR per night

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Sep 24 – Oct 1

R19,134 ZAR per night

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

Jun 11 – 18

R18,960 ZAR per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Nov 16 – 23

R18,809 ZAR per night

Private, pet-friendly home rentals

Guesthouse in Portland

5.0 out of 5 average rating, 73 reviews

Guesthouse Farm Stay

Dec 25 – Jan 1

R2,763 ZAR per night

Apartment in East Haddam

5.0 out of 5 average rating, 15 reviews

Country efficiency garden apt

Feb 15 – 22

R2,847 ZAR per night

Apartment in Guilford

4.91 out of 5 average rating, 23 reviews

Cozy Private Lake Q Retreat

May 25 – Jun 1

R3,669 ZAR per night

Cottage in Deep River

5.0 out of 5 average rating, 9 reviews

Serene Waterfront Cottage

Nov 2 – 9

R8,493 ZAR per night

Vacation home in East Hampton

5.0 out of 5 average rating, 25 reviews

Family Friendly Lake House Lake Pocotopaug Sunsets

Dec 1 – 8

R6,312 ZAR per night

Yurt in Killingworth

4.92 out of 5 average rating, 37 reviews

@Get_Yurty, wooden Yurt with 2 sleeping pods.

Oct 24 – 31

R4,431 ZAR per night

Guest suite in Guilford

4.93 out of 5 average rating, 76 reviews

Old Salt Oasis: serene, spacious, pets welcome!

Aug 3 – 10

R3,375 ZAR per night

Cottage in Deep River

4.87 out of 5 average rating, 23 reviews

Country Cottage in Private Garden Setting

Feb 20 – 27

R3,747 ZAR per night

Destinations to explore