We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Family-friendly vacation rentals in Middletown

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middletown

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

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.

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 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.

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.

Loft in Hartford

4.98 out of 5 average rating, 627 reviews

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Loft in Essex

4.94 out of 5 average rating, 429 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.

Treehouse in Willington

4.9 out of 5 average rating, 381 reviews

Treehouse | Countryside | Farm Animals | Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Home in Cheshire

5 out of 5 average rating, 128 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

Guest suite in New Haven

4.99 out of 5 average rating, 176 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Middletown family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Rental unit in Downtown New Haven

4.75 out of 5 average rating, 138 reviews

Luxury Penthouse Minutes to Yale

Condo in Norwich

4.84 out of 5 average rating, 149 reviews

Villa Flora @ Norwich Inn & Spa

Guest suite in Mansfield

4.96 out of 5 average rating, 201 reviews

Cozy private apt 8 mins from UCONN - solar powered

Home in Washington

4.94 out of 5 average rating, 17 reviews

Shrink Map to Best Washntn! "Senff 5BR"PoshPadSCT

Rental unit in Shelton

4.68 out of 5 average rating, 321 reviews

1ST FLR APT Your private resort, now FAMILY-ized!

Home in Colebrook

4.99 out of 5 average rating, 216 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Villa in Norwich

4.89 out of 5 average rating, 383 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

Family- and pet-friendly home rentals

Rental unit in Milford

4.87 out of 5 average rating, 260 reviews

The Farmhouse Estate Apartment

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Cottage in Guilford

4.99 out of 5 average rating, 123 reviews

"Red House on the Knoll" at Indian Cove

Home in North Fork

4.93 out of 5 average rating, 103 reviews

Maritime Village Getaway with Backyard

Guest suite in North Fork

4.92 out of 5 average rating, 155 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

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

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Cottage By The Sea

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 Shelter Island

4.98 out of 5 average rating, 41 reviews

Chic, serene, designer home with pool and views

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Condo in Farmington

4.8 out of 5 average rating, 51 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

Home in Litchfield

4.93 out of 5 average rating, 177 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Home in Fairfield

4.94 out of 5 average rating, 35 reviews

Newly-Renovated, Private, 4BR Cape w/Pool

Quick stats about vacation rentals that are family-friendly in Middletown

Total rentals
40 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore