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 favorite

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!)

Jan 26 – Feb 2

R4,888 ZAR per night

Guest favorite

Apartment in Middletown

4.94 out of 5 average rating, 709 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.

Oct 12 – 19

R2,249 ZAR per night

Guest favorite

Apartment in Guilford

4.98 out of 5 average rating, 251 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.

Aug 25 – Sep 1

R3,066 ZAR per night

Guest favorite

Farm stay in Hopkinton

4.98 out of 5 average rating, 193 reviews

Farm with a few goats on a lake close to beaches.

This is a bright walk out apartment in our home with a private entrance. We will be here but we give you all the privacy that you want. I have recently lost 3 goats. I still have two goats. This is a rural town 7 miles from Westerly, Rhode Island, and about 12 miles from Mystic. Please read the whole description of this property to make sure it is suitable for your family. Please read my reviews. I think my guests describe the accommodation even better than I do!

Dec 29 – Jan 5

R2,973 ZAR per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 168 reviews

Aqua Vista

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).

Jan 5 – 12

R2,583 ZAR per night

Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 230 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Jan 22 – 29

R3,203 ZAR per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 293 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.

Nov 22 – 29

R6,060 ZAR per night

Guest favorite

Loft in Hartford

4.98 out of 5 average rating, 540 reviews

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Mar 25 – Apr 1

R1,951 ZAR per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 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!

Oct 21 – 28

R3,140 ZAR per night

Guest favorite

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.

Oct 28 – Nov 4

R7,609 ZAR per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 158 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.

Jul 10 – 17

R2,781 ZAR 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.

Apr 12 – 19

R2,303 ZAR per night