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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.

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Rental unit in East Haddam

4.78 out of 5 average rating, 271 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Rental unit in Middletown

4.94 out of 5 average rating, 750 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Guest suite in Old Lyme

4.89 out of 5 average rating, 257 reviews

Luxurious Old Lyme King Bedroom Suite

First floor king bedroom suite in Ludington House, a historic home centrally located in the charming village of Old Lyme. Perfect for couples. Luxuriously appointed with California King bed, spacious kitchenette, bathroom and separate entrance. Private porch with view. Close to restaurants, beaches, art galleries and museum. Located in stunning historic mansion (location of film "Christmas at Pemberley Manor" 2018). Sorry - no pets, it will not work with our own pets. Guests must be 21 plus.

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Rental unit in Old Saybrook Center

4.97 out of 5 average rating, 119 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Home in Lyme

4.92 out of 5 average rating, 318 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

Guest suite in Brooklyn

4.93 out of 5 average rating, 171 reviews

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.

Cottage in Guilford

4.93 out of 5 average rating, 256 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Home in Essex

4.95 out of 5 average rating, 130 reviews

The Cozy Nook

Our Cozy Nook is a comfortable and spacious apartment with an open floor plan. Nestled in a peaceful country neighborhood makes it a relaxing get away. Nearby we have endless hiking trails, beaches, the Connecticut River and cozy villages with delicious dining, two professional theaters, galleries and one of a kind shops. The Nook offers a warm and welcoming place to stay while enjoying the surrounding area.

Loft in Essex

4.94 out of 5 average rating, 427 reviews

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. We gladly welcome clean, well behaved pets for an extra fee of $50. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Guest suite in North Fork

4.88 out of 5 average rating, 632 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Home in Old Lyme

4.94 out of 5 average rating, 263 reviews

Modern Luxurious CT Country Home

Beautiful mid-century modern glass and wood house in the forest, featuring tranquil designer spaces and continuously updated amenities. With only 2 hours from New York City and Boston, by train or by car, this is the ideal sanctuary for a perfect getaway. Minimum 2 nights during fall through spring months, 3 to 5-nights minimum in the summer months.

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Popular amenities for Westbrook family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest suite in Mansfield

4.96 out of 5 average rating, 200 reviews

Cozy private apt 8 mins from UCONN - solar powered

Home in North Fork

4.96 out of 5 average rating, 199 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Home in Wading River

4.96 out of 5 average rating, 486 reviews

Your Zen Retreat

Cottage in Southampton

4.96 out of 5 average rating, 176 reviews

Secluded Southampton Cottage w/Pool & Spa

Home in Stonington

4.97 out of 5 average rating, 206 reviews

Perfect New England Getaway has a pool/ hot tub

Home in Southampton

5 out of 5 average rating, 10 reviews

Hamptons Modern Retreat NEW CONS

Home in Southampton

4.83 out of 5 average rating, 210 reviews

Cozy & Chic Summer Getaway near village/beaches

Villa in Norwich

4.89 out of 5 average rating, 380 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

Family- and pet-friendly home rentals

Cottage in Middlefield

4.92 out of 5 average rating, 243 reviews

Lake Beseck cottage

Cottage in Charlestown

4.89 out of 5 average rating, 153 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

Home in North Fork

4.97 out of 5 average rating, 238 reviews

The Greenport Bungalow

Rental unit in Shelter Island Heights

4.91 out of 5 average rating, 244 reviews

Squire Chase House

Home in North Fork

4.91 out of 5 average rating, 100 reviews

North Fork Escape - Walk To Village, Beach, Parks

Bungalow in Montauk

4.9 out of 5 average rating, 570 reviews

Montauk Oceanview with Fireplace (2)

Guesthouse in Southport

4.96 out of 5 average rating, 187 reviews

Southport, CT across from BEACH

Home in Montauk

4.88 out of 5 average rating, 196 reviews

Studio MTK Bungalow. Short Walk to Beach & Town!

Family-friendly home rentals with a pool

Home in Montville

4.91 out of 5 average rating, 253 reviews

Casino Wine Down House***

Barn in Bethel

4.98 out of 5 average rating, 220 reviews

Escape to a Restored New England Antique Milk Barn

Home in New London

4.91 out of 5 average rating, 174 reviews

Sunset Oasis @ Ocean Beach: $1Mil View w/ 6 Queen

Home in Sag Harbor

4.81 out of 5 average rating, 133 reviews

Halloween / Autumn special - Sag Harbor Gem

Home in Monroe

4.96 out of 5 average rating, 199 reviews

Garden Level Suite with Beautiful Pool

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Home in Sag Harbor

4.85 out of 5 average rating, 258 reviews

Exclusive Sag Harbor Compound

Home in Southampton

4.95 out of 5 average rating, 148 reviews

Waterview, Dogs StayFree! Kayaks, Ping-Pong

Quick stats about vacation rentals that are family-friendly in Westbrook

Total rentals
100 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore