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Family-friendly vacation rentals in Middlesex County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middlesex County

Guests agree: these family-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, 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.

Cottage in Lebanon

4.87 out of 5 average rating, 146 reviews

Go Jump in the Lake!

NEWLY RENOVATED FOR THE 2023 SEASON! Our lake house is situated on 1.5 acres just 250 steps to the Cove Road boat launch on beautiful Amston Lake. The lake is a pristine 188-acre retreat located in Lebanon and Hebron, CT. Swimming, kayaking, canoeing, paddle boarding, fishing, and sunbathing are all activities you can enjoy. There are no motor boats allowed so you can enjoy all of those activities in a peaceful environment. Two beaches are located 1/2 or 1 mile away with ample parking at both

Cottage in Guilford

4.93 out of 5 average rating, 264 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”.

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.

Guest suite in Old Lyme

4.89 out of 5 average rating, 258 reviews

Luxurious Old Lyme King Bedroom Suite

First floor king bedroom suite in Ludington House, a historic home centrally located in the charming village of Old Lyme. Perfect for couples. Luxuriously appointed with California King bed, spacious kitchenette, bathroom and separate entrance. Private porch with view. Close to restaurants, beaches, art galleries and museum. Located in stunning historic mansion (location of film "Christmas at Pemberley Manor" 2018). Sorry - no pets, it will not work with our own pets. Guests must be 21 plus.

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

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.

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.

Home in Lyme

4.92 out of 5 average rating, 321 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

Loft in Essex

4.94 out of 5 average rating, 430 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.

Home in Old Lyme

4.94 out of 5 average rating, 264 reviews

Modern Luxurious CT Country Home

Beautiful mid-century modern glass and wood house in the forest, featuring tranquil designer spaces and continuously updated amenities. With only 2 hours from New York City and Boston, by train or by car, this is the ideal sanctuary for a perfect getaway. Minimum 2 nights during fall through spring months, 3 to 5-nights minimum in the summer months.

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Popular amenities for Middlesex County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Cutchogue

4.97 out of 5 average rating, 201 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Guest suite in Mansfield

4.96 out of 5 average rating, 201 reviews

Cozy private apt 8 mins from UCONN - solar powered

Home in Wading River

4.96 out of 5 average rating, 488 reviews

Your Zen Retreat

Cottage in Southampton

4.96 out of 5 average rating, 176 reviews

Secluded Southampton Cottage w/Pool & Spa

Home in Southampton

5 out of 5 average rating, 11 reviews

Hamptons Modern Retreat NEW CONS

Home in Southampton

4.83 out of 5 average rating, 210 reviews

Cozy & Chic Summer Getaway near village/beaches

Villa in Norwich

4.89 out of 5 average rating, 383 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

Home in Greenport

4.93 out of 5 average rating, 451 reviews

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Family- and pet-friendly home rentals

Home in East Hampton

4.77 out of 5 average rating, 52 reviews

MAGNIFICENT PRIVATE RIVERFRONT HOME, 10% off

Home in Guilford

4.97 out of 5 average rating, 65 reviews

Shoreline Cottage by Beach; Birder's Paradise

Rental unit in Guilford

5 out of 5 average rating, 5 reviews

Lakefront Country Oasis

Home in Deep River

4.53 out of 5 average rating, 38 reviews

Peace Barn in the heart of the CT River Valley

Home in Guilford

4.71 out of 5 average rating, 123 reviews

Purple Button Factory Sleeps 6 Walk to Town Green

Home in Old Saybrook

4.95 out of 5 average rating, 41 reviews

Escape to our Waterfront House In Old Saybrook CT

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 reviews

Quiet 2 bed room apt w/ private entrance.

Home in Lyme

4.9 out of 5 average rating, 91 reviews

Luxurious country guest house

Family-friendly home rentals with a pool

Home in Montville

4.91 out of 5 average rating, 254 reviews

Casino Wine Down House***

Home in New London

4.91 out of 5 average rating, 175 reviews

Sunset Oasis @ Ocean Beach: $1Mil View w/ 6 Queen

Home in East Hampton

4.93 out of 5 average rating, 107 reviews

Private & Pristine with Pool and Kid’s Playard

Home in Hampton Bays

4.94 out of 5 average rating, 121 reviews

Peaceful Retreat in Immaculate Architect’s House

Home in Sag Harbor

4.81 out of 5 average rating, 134 reviews

Thanksgiving! Sag Harbor Gem!

Home in Cheshire

5 out of 5 average rating, 128 reviews

Pool House

Home in Southampton

4.94 out of 5 average rating, 270 reviews

Southampton Village Classic-Summer Special!

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Destinations to explore