
Family-friendly vacation rentals in Westbrook
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Westbrook
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Rural Homestead Stay in Your a Private Suite
Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard amongst the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

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.

Unique apartment in former art gallery.
The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. One bedroom on the ground floor with full bath nearby. The other bedroom is in the loft with queen bed with a daybed in the sitting area for two extra guests. We gladly welcome clean, well behaved pets. ($50 pet fee) Pet sitting and dog walking available for an additional fee. On site babysitting also available.

Peaceful Riverfront Cottage w/Dock, Walk to Beach
This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Water Forest Retreat -Octagon
Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Urban Garden Suite
Relax & Recharge in Westville’s Hidden Gem in New Haven. Unwind in this serene, beautiful, cozy, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

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.

Lovely Garden-Level Apartment in Heart of Town
This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

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.

Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

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!

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!
Popular amenities for Westbrook family-friendly rentals
Family-friendly home rentals with a hot tub

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Luxury cottage by the sea with hot tub and pool

Peaceful Oasis steps from Mohegan Sun

Guilford Lakes Cottage, with hot tub and fire pit.

Morgan Suite - spacious | hot tub | water views!

Cozy Getaway | Pet Friendly | Litchfield Cty

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

Lakeside cottage with beautiful views up the lake!
Family- and pet-friendly home rentals

Modern & Cozy Beach House - Walk to Ocean Beach

Geodesic Dome in the Wooods

Clean & quiet 2 bedroom w/office-dog friendly

Town's End Farm

Private 1 bedroom apartment in central Connecticut

59 Old Maids Lane pool house

Walk to the beach at Black Point, Niantic, Ct

Lakeside apartment 2.5 miles from Wesleyan campus!
Family-friendly home rentals with a pool

Charming Guest Cottage with Modern Amenities

Private Villa, Pool, New King Bed, close to casino

Romantic Spa Retreat minutes to Mohegan Sun Casino

Garden Level Suite with Beautiful Pool

FREE Private Indoor Heated Pool - Mystic Home

The Vacay Villa

Montauk Oceanview

The Pond Mill Retreat w/ 2 Bdrms & Pool
When is the best time to visit Westbrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $288 | $307 | $292 | $287 | $337 | $358 | $395 | $413 | $370 | $310 | $327 | $314 |
| Avg. temp | 31°F | 33°F | 40°F | 50°F | 60°F | 70°F | 76°F | 74°F | 68°F | 56°F | 46°F | 37°F |
Quick stats about vacation rentals that are family-friendly in Westbrook

Total vacation rentals
Explore 100 vacation rentals in Westbrook

Nightly prices starting at
Westbrook vacation rentals start at $50 per night before taxes and fees

Verified guest reviews
Over 2,680 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
100 of Westbrook vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westbrook rentals

4.8 Average rating
Westbrook stays are highly rated by guests—averaging 4.8 out of 5!
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