Family-friendly vacation rentals in Westbrook

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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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Guest favourite

Cabin in Old Lyme

4.95 out of 5 average rating, 109 reviews

Early 1900s Log Cabin at Rogers Lake - Suite Style

Authentic historical log cabin built in the early 1900's. It's easy to spend hours just taking in the amazing detail and character this cabin has to offer. Meticulously decorated with new furnishings, a perfect blend of camping and suite-style lodging (while in comfort, with new AC & heating system). Enjoy a quiet getaway, submerged in nature that's only minutes from 95! Local beaches, lake, museums, hiking, shops with easy access to casinos, Mystic and more! (Click photos for more details!)

Aug. 22 – 29

$416 CAD per night

Guest favourite

Apartment in Middletown

4.94 out of 5 average rating, 706 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.

Apr. 11 – 18

$194 CAD per night

Guest favourite

Apartment in Guilford

4.98 out of 5 average rating, 250 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.

Oct. 29 – Nov. 5

$263 CAD per night

Guest favourite

Guesthouse in Charlestown

4.88 out of 5 average rating, 269 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Feb. 19 – 26

$156 CAD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Feb. 16 – 23

$188 CAD per night

Guest favourite

Guest suite in Groton

4.9 out of 5 average rating, 157 reviews

Shoreline Retreat Groton-Mystic Region

Shoreline area guest suite with private entrance, private bath, private deck and on-site and off-street parking directly across the street. The property is located across from a public golf course, one block from the beach and the University of Connecticut Avery Point campus. It is approx. 5 miles to Mystic, Ct and close proximity to the casinos, the Coast Guard Academy, Pfizer, Electric Boat, the Naval Submarine Base and Tanger Outlets at Foxwoods Casino.

Jul. 20 – 27

$202 CAD per night

Guest favourite

Home in Lyme

4.91 out of 5 average rating, 292 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.

Dec. 5 – 12

$522 CAD per night

Guest favourite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

Scenic lake-front guest suite and access to 2 kayaks. Lake is ideal for swimming, fishing and paddle boarding. Five minutes to the Amtrak station, thirty to Newport, RI and fifteen to RI's best beaches. If you are interested in touring New England, the location is ideal for day trips to Martha's Vineyard, Boston, and NYC. Property sits in the shadow of URI. The suite sleeps up to 2 comfortably, with a queen-sized bed.

Jun. 13 – 20

$220 CAD per night

Guest favourite

Home in Old Lyme

4.94 out of 5 average rating, 257 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.

Jan. 12 – 19

$672 CAD per night

Guest favourite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

Housed in a 100-year-old building nestled between the Victorian houses in New Haven's historic City Point neighborhood, once the center of New England's oyster trade, our cottage is a two-block walk from the marina (and its award-winning restaurant), a 10 minute-drive from the West Haven beaches and a few minutes' drive to Yale.

May 27 – Jun. 3

$240 CAD per night

Superhost

Apartment in East Haddam

4.78 out of 5 average rating, 260 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.

Feb. 11 – 18

$223 CAD per night

Guest favourite

Apartment in Portland

4.88 out of 5 average rating, 461 reviews

SUNNY PRIVATE 1 BEDROOM APARTMENT

Feel right at home in this modern meets traditional 1 bedroom apartment. Features a full kitchen, living room and reading nook/office . A short 5-10 minute drive to Wesleyan University, Downtown Middletown, Middlesex Hospital and Saint Clements Castle.

Jun. 24 – Jul. 1

$153 CAD per night