Family-friendly vacation rentals in Essex

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Essex

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

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Guest favorite

Cabin in Old Lyme

4.95 out of 5 average rating, 109 reviews

Early 1900s Log Cabin at Rogers Lake - Suite Style

Authentic historical log cabin built in the early 1900's. It's easy to spend hours just taking in the amazing detail and character this cabin has to offer. Meticulously decorated with new furnishings, a perfect blend of camping and suite-style lodging (while in comfort, with new AC & heating system). Enjoy a quiet getaway, submerged in nature that's only minutes from 95! Local beaches, lake, museums, hiking, shops with easy access to casinos, Mystic and more! (Click photos for more details!)

Dec 31 – Jan 7

G$52,953 GYD per night

Guest favorite

Apartment in Middletown

4.94 out of 5 average rating, 707 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.

Oct 8 – 15

G$25,281 GYD per night

Guest favorite

Apartment in Guilford

4.98 out of 5 average rating, 251 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.

Aug 4 – 11

G$34,459 GYD per night

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Mar 2 – 9

G$24,461 GYD per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 292 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.

Dec 29 – Jan 5

G$72,683 GYD per night

Guest favorite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Apr 18 – 25

G$15,388 GYD per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Oct 21 – 28

G$35,288 GYD per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 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.

Jan 25 – Feb 1

G$85,529 GYD per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 158 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.

Jul 6 – 13

G$31,777 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.

Sep 25 – Oct 2

G$25,889 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 24 – Jul 1

G$19,347 GYD per night

Guest favorite

Apartment in Mansfield

4.98 out of 5 average rating, 268 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 14 – 21

G$28,808 GYD per night