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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, 275 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, 348 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, 756 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, 128 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, 628 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, 253 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, 153 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, 104 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!

Loft in Chester

4.99 out of 5 average rating, 116 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 Old Saybrook

4.96 out of 5 average rating, 120 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.

Rental unit in East Haddam

4.9 out of 5 average rating, 150 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 Deep River

4.81 out of 5 average rating, 194 reviews

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Middlesex County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in Old Saybrook

5 out of 5 average rating, 25 reviews

Romantic Couples Retreat with Private Sandy Beach

Home in Westbrook

4.95 out of 5 average rating, 20 reviews

Barnacle Bay Beach House

Home in Clinton

5 out of 5 average rating, 6 reviews

Boulder Lake House Retreat

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, 114 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Home in Essex

4.98 out of 5 average rating, 51 reviews

Ideal Historic Home in Essex Village

Home in Old Lyme

4.9 out of 5 average rating, 125 reviews

The Beach House

Kid-friendly apartment rentals

Rental unit in Killingworth

4.88 out of 5 average rating, 33 reviews

Life on the Farm

Rental unit in Guilford

4.97 out of 5 average rating, 60 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 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, 156 reviews

Charming Chester Retreat - Cottage

Rental unit in Middletown

4.89 out of 5 average rating, 277 reviews

3 bedroom near Wesleyan, downtown

Rental unit in Middletown

4.96 out of 5 average rating, 27 reviews

Your Sweet Spot in Middletown CT

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Kid-friendly condo rentals

Condo in New Britain

4.81 out of 5 average rating, 118 reviews

New Britain "Joy of Small Space" Condo

Condo in Middletown

4.96 out of 5 average rating, 135 reviews

Entire place to yourself Cromwell/Middletown Line

Condo in Norwich

4.97 out of 5 average rating, 117 reviews

The Vacay Villa

Condo in Norwich

4.98 out of 5 average rating, 156 reviews

Peaceful Oasis steps from Mohegan Sun

Condo in Greenport

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

Condo in Greenport

4.9 out of 5 average rating, 113 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

4.88 out of 5 average rating, 229 reviews

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

Destinations to explore