Family-friendly vacation rentals in Westport

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Top-rated family-friendly rentals in Westport

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 113 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Jan 16 – 23

ﺩ.ﺇ432 per night

Guest favorite

Apartment in Norwalk

4.92 out of 5 average rating, 295 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Dec 26 – Jan 2

ﺩ.ﺇ428 per night

Guest favorite

Home in Fairfield

4.96 out of 5 average rating, 290 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

Apr 16 – 23

ﺩ.ﺇ886 per night

Guest favorite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

Sep 3 – 10

ﺩ.ﺇ585 per night

Guest favorite

Guesthouse in Oyster Bay

4.96 out of 5 average rating, 179 reviews

GORGEOUS & SERENE in Oyster Bay - LI/NY

Our small, modern bungalow is completely private. Perfect for working as it is for a romance, or just coming to LI-NY for the weekend. The luxurious queen bed is great, alone, or shared, and the custom sofa converts into another bed or two in a pinch (ask us about this before booking, it's got its limits); keep in mind that this is an open loft-like space. We're located on Long Island's North Shore, close to beaches yet only 45-minutes from Manhattan, and less than an-hour to The Hampton's.

Nov 6 – 13

ﺩ.ﺇ1,028 per night

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Oct 15 – 22

ﺩ.ﺇ525 per night

Guest favorite

Barn in Bethel

4.98 out of 5 average rating, 203 reviews

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Apr 17 – 24

ﺩ.ﺇ769 per night

Guest favorite

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.

Jun 24 – Jul 1

ﺩ.ﺇ550 per night

Guest favorite

Apartment in Ardsley

4.9 out of 5 average rating, 380 reviews

Lovely and well-appointed suite with full privacy

Charming suite with a private entrance, bathroom, indoor parking and dining area with kitchen amenities. Conveniently located in Westchester, and is accessible by the I-87, Henry Hudson, Sprain and Saw Mill Parkways; only a thirty minute drive to NYC. Near a deli, grocery, bakery, Carvel, CVS and a selection of restaurants.

Feb 28 – Mar 7

ﺩ.ﺇ402 per night

Guest favorite

Guesthouse in South Salem

4.93 out of 5 average rating, 220 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Jan 3 – 10

ﺩ.ﺇ734 per night

Guest favorite

Guesthouse in Fairfield

4.96 out of 5 average rating, 173 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

Feb 12 – 19

ﺩ.ﺇ960 per night

Guest favorite

Home in Stamford

4.98 out of 5 average rating, 212 reviews

Bright Stylish Chic 4BR 4BA Home

Welcome to this sunny, chic, spacious 4BR, 4BA North Stamford country house with lots of character and a huge backyard. Great for families. Light & bright, open flow, skylights galore, deck and grill, spacious playroom. Large primary bedroom suite. Just 1 hour from NYC.

Oct 30 – Nov 6

ﺩ.ﺇ2,063 per night