Family-friendly vacation rentals 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

Wizard's Roost and Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

The Cottage

Step into a piece of history with this charming, fully converted 1930s changing house. Ideally located, it’s just a short stroll to downtown or a scenic bike ride to the beach, putting the best of the area right at your doorstep. Inside, you’ll discover a thoughtfully designed studio layout, offering the perfect setting for a peaceful getaway. The Cottage seamlessly blends comfort, convenience, and character, creating a truly inviting retreat.

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

Unique apartment in former art gallery.

A private apartment in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. A spacious and open floor plan offers a peaceful stay along with thoughtful touches with your comfort in mind.