Family-friendly holiday 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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Top Guest favourite

A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.

Guesthouse in Portland

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 364 reviews

Guest favourite

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Indoor spacesKitchenNearby

4.95 out of 5 average rating, 213 reviews

Guest favourite

An aerial view of the farm showcases expansive green grounds interspersed with tree cover and pathways. Several fenced areas and horse barns are visible, along with well-maintained fields. The surrounding nature creates a serene environment, inviting a sense of peace and relaxation.

Guest suite in Killingworth

Life on the Farm

Imagine living on a horse farm! Enjoy the wildlife, & watch horses graze right from your steps. Relax, at this unique tiny getaway. As you drive down the entry to Fortunato Farm, you’ll feel a level of comfort allowing relaxation. Open the door, sip your coffee in the sunshine. You're in the country, yet close to CT shoreline areas & restaurants, Clinton Town Beach, and only 15 minutes to Middletown. 25 Miles to Tweed Airport and 45 Miles to Bradley International. 37 miles to Mystic & Mohegan

Indoor spacesFamilyWalkability

4.92 out of 5 average rating, 106 reviews

Top Guest favourite

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

KitchenIndoor spacesView

4.93 out of 5 average rating, 369 reviews

Guest favourite

The red yurt is set among tall trees, showcasing a spacious wooden deck surrounded by a lattice railing. Large windows allow natural light to enter, while the soft curves of the yurt blend harmoniously into the wooded landscape.

Yurt in Guilford

Hartwoods Yurt

Enjoy a unique wilderness getaway and unwind in a peaceful, 10.3 acre wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

FamilyIndoor spacesHeating

4.88 out of 5 average rating, 154 reviews

Guest favourite

A two-story beach cottage is presented with a light exterior and a spacious balcony. Large sliding glass doors are visible at the lower level, providing easy access to the outdoor space. Nearby, a driveway is seen leading towards the garage.

Cottage in Westbrook

A Beach House Gem

Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

Indoor spacesKitchenNearby

4.91 out of 5 average rating, 114 reviews

Top Guest favourite

The front exterior of the cottage is shown, featuring a stone pathway leading to the entrance. An orange front door is framed by white railings. Surrounding greenery and seasonal decor complement the inviting atmosphere of the landscaped yard.

Cottage in Chester

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.

KitchenFamilyShared spaces

4.97 out of 5 average rating, 315 reviews

Top Guest favourite

The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.

Cottage in East Haddam

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

Indoor spacesFamilyParks

5.0 out of 5 average rating, 120 reviews

Top Guest favourite

A white two-story house is featured, with black-shuttered windows and a decorative front porch lantern. An American flag flutters at the front, and a neatly maintained fence surrounds the lawn. A tree without leaves is visible in the background on a clear day.

Home in Essex

Ideal Historic Home in Essex Village

Welcome to village life in the heart of Essex Village. This is the longest running and most visited vacation rental home on Main St in Essex, CT. Chosen as the best small town in America by Norman Crampton in his book, The 100 Best Small Towns in America. Essex also appears in 1000 Places to Visit Before You Die. Located on the Connecticut River, this friendly New England community has been welcoming travelers since before the American Revolution.

KitchenFamilyParking

4.97 out of 5 average rating, 102 reviews

Guest favourite

The exterior of a single-story apartment features a beige facade with brown trim. A welcoming front door is flanked by potted plants, and a covered porch is visible. Natural light illuminates the surroundings from a clear blue sky.

Apartment in East Haddam

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.

FamilyIndoor spacesCondition

4.88 out of 5 average rating, 236 reviews

Top Guest favourite

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

FamilyIndoor spacesHiking

4.99 out of 5 average rating, 180 reviews

Top Guest favourite

A unique round structure is surrounded by lush greenery, highlighting a gravel patio area furnished with white seating. The wooden design includes multiple windows, providing natural light to the interior and maintaining a connection to the outdoor environment.

Yurt in Killingworth

@Get_Yurty w/ 2 sleeping pods, NO Cleaning/Pet fee

@Get_Yurty is a wooden round house set in a beautiful treelined area of Connecticut. The Yurt design being utilized in this structure provides a unique experience of 360 degree views of the outside along with modern amenities like private sleep pods, all major appliances, climate control and full modern bathroom. Disclaimer - this is NOT a tent!

FamilyIndoor spacesLayout

4.96 out of 5 average rating, 113 reviews