Family-friendly vacation rentals in Old Saybrook

Guesthouse in North Stonington

A serene landscape is presented, featuring expansive green fields under a softly glowing sunrise. Two rustic buildings are visible: a barn with classic doors and a white cottage, both surrounded by lush trees and open space, reflecting the peaceful countryside setting.

4.99 out of 5 average rating, 245 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

FamilyIndoor spacesLong stay

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, 144 reviews

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

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Indoor spacesFamilyAmenities

5.0 out of 5 average rating, 107 reviews

A cozy houseboat is seen floating on the water, featuring a welcoming porch with two light blue chairs. The reflection of the boat and surrounding trees is visible in the calm river, highlighting the serene atmosphere of the setting.

Boat in Old Lyme

Sunny Daze

This dreamy houseboat rests gently at a family-owned marina, where time seems to slow and nature leans in close. Surrounded by peaceful river views, tall grasses, and birdsong, it’s a floating haven for those seeking calm and creativity. Whether you’re sipping coffee on the deck at sunrise or watching the moon ripple across the water, this riverside retreat invites you to drift, dream, and just be. Enjoy a fire or jump on a paddle board or kayak f or an adventure down the river it has it all!

FamilyIndoor spacesDecor

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.

4.92 out of 5 average rating, 104 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.

FamilyKitchenQuiet

4.98 out of 5 average rating, 165 reviews

A welcoming view of Belle Vue Cottage features a well-kept lawn with a sign indicating its name. The cottage is framed by trees, with a driveway leading to it. A garage is visible in the background, contributing to the serene atmosphere of the neighborhood.

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.

FamilyIndoor spacesBackyard

5.0 out of 5 average rating, 100 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.

KitchenFamilyLaundry

5.0 out of 5 average rating, 108 reviews

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 spacesKitchenCondition

4.75 out of 5 average rating, 254 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.

Indoor spacesKitchenAccuracy

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, 113 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!

KitchenFamilyGrill

4.97 out of 5 average rating, 326 reviews

The living area features a vaulted ceiling with bright natural light streaming through large windows. A cozy seating arrangement includes a light grey couch and a comfortable chair. A stylized coffee table sits in the center, with a dining table set for two nearby.

Cottage in East Lyme

Your Nest Near The Beach

Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.

KitchenFamilyBeach

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.

4.98 out of 5 average rating, 110 reviews

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!

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 106 reviews

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

Adorable Beach House on LI Sound

Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream

Indoor spacesFamilyGetting around

Popular amenities for Old Saybrook family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 206 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

KitchenFamilyAccess

Superhost

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

4.9 out of 5 average rating, 249 reviews

Walk to Casino with POOL+HOT TUB

Indoor spacesFamilyWalkability

4.99 out of 5 average rating, 171 reviews

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

Cozy cottage 5 minutes from UConn

FamilyIndoor spacesGetting around

4.93 out of 5 average rating, 345 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!

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 200 reviews

A vibrant backyard features a spacious pool with clear blue water, complemented by a wooden deck and a shaded seating area under an umbrella. The two-story house stands in the background, surrounded by greenery, creating a peaceful outdoor environment.

Home in Montville

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

Indoor spacesKitchenAccess

4.91 out of 5 average rating, 128 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!

KitchenIndoor spacesValue

4.99 out of 5 average rating, 184 reviews

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

Luxe Bolton Lake

FamilyIndoor spacesLocation

4.89 out of 5 average rating, 256 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!

KitchenFamilyDecor

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 109 reviews

A living room features natural light streaming through windows, enhancing the warm wood floors. A brown sofa is paired with a woven lounge chair, and a blue coffee table is centered on a light-patterned rug. Wall-mounted shelves display framed art and decorative items.

Cottage in Old Saybrook

1920’s charming dollhouse near South Cove

KitchenIndoor spacesComfort

Superhost

A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.

Cottage in Westbrook

4.86 out of 5 average rating, 226 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

Indoor spacesFamilyHiking

4.95 out of 5 average rating, 366 reviews

Bungalow in Old Lyme

Pet Friendly Bungalow!!!

Indoor spacesKitchenBackyard

Superhost

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

4.82 out of 5 average rating, 136 reviews

Insta-worthy * Couples Retreat

KitchenIndoor spacesNearby

4.94 out of 5 average rating, 473 reviews

The exterior of a two-story building is depicted, featuring natural wood siding and multiple windows. A gravel path leads to a covered entrance surrounded by benches and flower planters. Large trees provide shade, enhancing the serene atmosphere of the setting.

Loft in Essex

Unique apartment in former art gallery.

Indoor spacesKitchenWalkability

4.89 out of 5 average rating, 535 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

FamilyIndoor spacesView

4.98 out of 5 average rating, 341 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

KitchenIndoor spacesLong stay

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

FamilyIndoor spacesCheck-in

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 138 reviews

A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.

Barn in Bloomfield

Farm Stay with Horses & Pool | Mountaintop Views

KitchenIndoor spacesQuiet

4.92 out of 5 average rating, 130 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

FamilyKitchenAmenities

4.94 out of 5 average rating, 250 reviews

A spacious sleeping area features a canopy bed with an orange quilt. Surrounding the room are colorful artworks and wooden sculptures. Natural light enters through windows, highlighting the eclectic decor and greenery from nearby plants.

Home in Scituate

Artist studio in the woods

Indoor spacesKitchenWifi

4.98 out of 5 average rating, 359 reviews

A comfortable living area features a gray sectional sofa with a chaise lounge, positioned across from a minimalist entertainment unit. Natural light filters through sliding glass doors that lead to a patio. A dining area is visible in the background, accompanied by bar stools.

Condo in Norwich

Top Rated Villa located near Mohegan Sun & Mystic

KitchenIndoor spacesValue

4.98 out of 5 average rating, 251 reviews

Condo in Norwich

Peaceful Oasis steps from Mohegan Sun

FamilyKitchenLong stay

4.96 out of 5 average rating, 238 reviews

Guest suite in Mansfield

Cozy private apt 8 mins from UCONN - solar powered

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 207 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

FamilyIndoor spacesCheck-in