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.

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Guest favorite

Apartment in Middletown

4.94 out of 5 average rating, 706 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.

Mar 4 – 11

G$25,323 GYD per night

Guest favorite

Home in East Haven

4.88 out of 5 average rating, 196 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Feb 14 – 21

G$32,463 GYD per night

Guest favorite

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.

Mar 10 – 17

G$23,842 GYD per night

Guest favorite

Apartment in Southington

4.93 out of 5 average rating, 269 reviews

#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*

You're looking at a new construction Mid-Century Modern inspired In-Law Apartment with private access located in a beautiful, quiet neighborhood right in central CT just 1 minute from I-84. Pet fee $25/night per animal The unit features a large backyard with a patio, fire pit and chairs for your enjoyment. Fires must be approved by host. NOTE: THIS AIRBNB IS ONLY SUITABLE FOR UP TO FOR 4 ADULTS AND 1 CHILD. PLEASE ASK ME IF YOU HAVE ANY QUESTIONS OR CONCERNS.

Aug 6 – 13

G$25,899 GYD per night

Guest favorite

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 1 – 8

G$36,058 GYD per night

Guest favorite

Loft in Hartford

4.98 out of 5 average rating, 537 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.

Sep 28 – Oct 5

G$22,029 GYD per night

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 118 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.

Apr 1 – 8

G$30,203 GYD per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 157 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.

Jun 24 – Jul 1

G$31,308 GYD per night

Superhost

Apartment in East Haddam

4.78 out of 5 average rating, 260 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.

Feb 6 – 13

G$25,932 GYD per night

Guest favorite

Apartment in Portland

4.88 out of 5 average rating, 464 reviews

SUNNY PRIVATE 1 BEDROOM APARTMENT

Feel right at home in this modern meets traditional 1 bedroom apartment. Features a full kitchen, living room and reading nook/office . A short 5-10 minute drive to Wesleyan University, Downtown Middletown, Middlesex Hospital and Saint Clements Castle.

Jun 25 – Jul 2

G$19,379 GYD per night

Guest favorite

Home in Middletown

4.88 out of 5 average rating, 266 reviews

Historic Greek Revival Brick Home

Private First Floor Apartment of an 1849 historical home in the heart of Middletown, CT. One block to Main street with many great restaurants, Wesleyan University & across from the public library. Lovely fenced in yard, ornately covered side porch.

Aug 16 – 23

G$27,894 GYD per night

Guest favorite

Apartment in Mansfield

4.98 out of 5 average rating, 267 reviews

Green Energy Ecohaven

Our fully-furnished, 1000-square-foot, attached apartment makes sustainability comfortable. From the solar panels outside to the life-affirming wood interior, this apartment exudes positive energy. Relax and enjoy the architecturally unique features.

Feb 21 – 28

G$28,855 GYD per night