Family-friendly holiday rentals in Westbrook

4.97 out of 5 average rating, 227 reviews

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in Niantic

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

4.8 out of 5 average rating, 147 reviews

A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.

Home in Westbrook

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

A wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.

4.93 out of 5 average rating, 107 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

4.91 out of 5 average rating, 113 reviews

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

4.96 out of 5 average rating, 227 reviews

A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.

Home in Clinton

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

4.98 out of 5 average rating, 169 reviews

Cottage in Old Saybrook

Belle Vue 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.

5.0 out of 5 average rating, 105 reviews

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace

Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

4.97 out of 5 average rating, 101 reviews

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.

4.89 out of 5 average rating, 101 reviews

The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.

Home in Westbrook

Zion's Light Beach Cottage

YEAR ROUND BEACH HOUSE. ALL AIRBNB FEES INCLUDED IN RATE! Unwind and make memories at Zion’s Light Beach Cottage. Westbrook, CT. Private beach association. This 2 bed, 1 bath has been designed with coastal comfort in mind. Open concept. Modern and fully equipped. Lux bedding. Dine in or patio style. Gas grill. Outdoor shower. All within a 3 minute walk to the beach. Heading out? The CT Shoreline has plenty to do. Check out our guidebook!

4.75 out of 5 average rating, 261 reviews

A charming entrance is framed by an archway adorned with decorative ironwork. The door, painted in a soft turquoise, is complemented by a welcoming wreath. Lush green foliage surrounds the entryway, creating a serene outdoor environment.

Cottage in Old Saybrook

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.

A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.

4.92 out of 5 average rating, 119 reviews

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!

Guest suite in Old Saybrook

A bright living space features vaulted ceilings and modern light fixtures. Two armchairs are positioned beside a wooden table with a decorative plant. A television is mounted on the wall, and natural light filters through sheer curtains, enhancing the inviting ambiance.

Cozy Loft Getaway

Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

4.98 out of 5 average rating, 116 reviews

Popular amenities for Westbrook family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 212 reviews

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

4.99 out of 5 average rating, 113 reviews

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

4.97 out of 5 average rating, 206 reviews

A private hot tub is illuminated with soft blue lighting, surrounded by trees and a wooden fence. String lights add a warm glow to the area, creating a serene atmosphere for relaxation under the evening sky.

Home in Montville

Casino Stay & Play House w/Hot Tub, Game Room

4.92 out of 5 average rating, 134 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

4.93 out of 5 average rating, 363 reviews

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!

4.9 out of 5 average rating, 260 reviews

A wooden table set for dining overlooks a serene lake. Glassware and plates filled with food are arranged on the table, while white chairs offer seating. Lush greenery lines the shore, complementing the calm water and bright sky.

Cottage in Ledyard

Waterfront cottage overhanging the water!

4.88 out of 5 average rating, 260 reviews

A hot tub is situated on a stone patio, surrounded by lush greenery. A short set of steps leads up to its edge, and vibrant flowers add a splash of color in the background. The hot tub's cover is partially open, revealing inviting water.

Home in Montville

Walk to Casino with POOL+HOT TUB

4.91 out of 5 average rating, 263 reviews

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Family- and pet-friendly home rentals

A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.

4.97 out of 5 average rating, 146 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

4.82 out of 5 average rating, 139 reviews

A charming beach cottage exterior is presented, featuring a light gray shingle façade and a welcoming pink front door. The screened-in porch offers views of the surrounding sandy area, with steps leading up from the ground level. A whimsical lobster sign is visible at the porch's base.

Bungalow in Old Lyme

Insta-worthy * Couples Retreat

4.89 out of 5 average rating, 543 reviews

A charming cottage exterior is showcased with a welcoming entrance door framed by green shutters. Two colorful adirondack chairs are positioned beside a potted yellow flower arrangement. Green bushes line the pathway, enhancing the serene garden setting.

Bungalow in Clinton

Shalom Cottage Private Beach Access

4.99 out of 5 average rating, 179 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

4.97 out of 5 average rating, 358 reviews

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

4.94 out of 5 average rating, 310 reviews

The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.

Cottage in Guilford

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

4.98 out of 5 average rating, 171 reviews

A serene view of a quiet street leading to the water, framed by trees. Visible are parked vehicles along the roadside, with the sparkling bay in the background, indicating proximity to the beach. A basketball hoop stands on the right side, contributing to the residential atmosphere.

Home in East Lyme

Walk to the beach at Black Point, Niantic, Ct

4.92 out of 5 average rating, 174 reviews

A tranquil beach scene captures the shoreline of Niantic Bay, lined with charming homes. The calm water reflects the soft hues of the sky, while gentle waves lap at the sandy beach. A few people can be seen enjoying the serene environment in the distance.

Home in Niantic

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 142 reviews

An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.

Apartment in Montauk

Ocean View Studio with King Bed

4.89 out of 5 average rating, 175 reviews

A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.

Home in New London

Beauty and the Beach!

4.99 out of 5 average rating, 147 reviews

The indoor heated pool features a bright blue expanse of water inviting for a refreshing swim. Comfortable lounge seating is positioned nearby, and a bar area provides space for poolside refreshments. Large sliding glass doors bring in natural light and offer views of the serene outdoor setting.

Home in Stonington

Heated Indoor Pool • 4 King Beds • Walk Downtown

4.88 out of 5 average rating, 173 reviews

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in Greenport

Waterfront Escape | Private Beach, Pool & Views

4.89 out of 5 average rating, 134 reviews

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

Home in Springs

4 BD w/ Heated Pool in E Hampton, Fully Furnished

4.86 out of 5 average rating, 136 reviews

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

Condo in Greenport

Beautiful condo on Long Islands Northfork

4.86 out of 5 average rating, 139 reviews

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

Home in Sag Harbor

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)