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Kid-friendly vacation rentals in Middlesex County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Middlesex County

Guests agree: these kid-friendly rentals 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.

Rental unit in Chester

4.93 out of 5 average rating, 343 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Rental unit in Middletown

4.94 out of 5 average rating, 750 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

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.

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.*

Cottage in Chester

4.98 out of 5 average rating, 252 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

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.

Home in Haddam

5 out of 5 average rating, 101 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Rental unit in Deep River

4.92 out of 5 average rating, 132 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Loft in Chester

4.99 out of 5 average rating, 112 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

Rental unit in East Haddam

4.9 out of 5 average rating, 149 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

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Popular amenities for Middlesex County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Westbrook

4.86 out of 5 average rating, 178 reviews

Family-Friendly Cottage by The Shore

Home in Westbrook

4.94 out of 5 average rating, 17 reviews

Barnacle Bay Beach House

Home in Old Saybrook

5 out of 5 average rating, 23 reviews

Romantic Couples Retreat with Private Sandy Beach

Home in Clinton

5 out of 5 average rating, 4 reviews

Boulder Lake House Retreat

Home in Essex

4.98 out of 5 average rating, 48 reviews

Ideal Historic Home in Essex Village

Home in Madison

5 out of 5 average rating, 39 reviews

Writer's Retreat & Explorer's Adventure!

Home in Haddam

4.96 out of 5 average rating, 24 reviews

The Farmhouse Stay

Home in East Haddam

4.86 out of 5 average rating, 42 reviews

Historic House by the River

Kid-friendly apartment rentals

Rental unit in Killingworth

4.93 out of 5 average rating, 29 reviews

Life on the Farm

Rental unit in Guilford

4.96 out of 5 average rating, 55 reviews

Cozy Private Lake Q Retreat

Rental unit in Old Lyme

4.89 out of 5 average rating, 195 reviews

Private apartment in historic Old Lyme mansion

Rental unit in Old Saybrook

4.97 out of 5 average rating, 119 reviews

Convenient and Cute in Downtown Old Saybrook

Rental unit in Branford

4.97 out of 5 average rating, 103 reviews

Ridgeview Suite at Stony Creek Depot

Rental unit in Chester

4.98 out of 5 average rating, 152 reviews

Charming Chester Retreat-Hidden Gem

Rental unit in Middletown

4.89 out of 5 average rating, 271 reviews

3 bedroom near Wesleyan, downtown

Rental unit in Middletown

4.96 out of 5 average rating, 25 reviews

Your Sweet Spot in Middletown CT

Kid-friendly condo rentals

Condo in New Britain

4.82 out of 5 average rating, 117 reviews

New Britain "Joy of Small Space" Condo

Condo in Middletown

4.96 out of 5 average rating, 131 reviews

Entire place to yourself Cromwell/Middletown Line

Condo in Greenport

4.89 out of 5 average rating, 145 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in Norwich

4.97 out of 5 average rating, 113 reviews

The Vacay Villa

Condo in Norwich

4.98 out of 5 average rating, 155 reviews

Peaceful Oasis steps from Mohegan Sun

Condo in Greenport

4.9 out of 5 average rating, 109 reviews

Seaside Escape w Pool, Private Beach & Patio

Condo in Greenport

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Condo in Norwich

4.89 out of 5 average rating, 227 reviews

The N-V ...The Spa at the Norwich Inn.

Destinations to explore