Family-friendly vacation rentals in Woodbury

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Woodbury

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

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Guest favorite

Home in Morris

4.87 out of 5 average rating, 142 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Jan 20 – 27

G$85,058 GYD per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 19 – 26

G$31,849 GYD 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.

Aug 7 – 14

G$29,824 GYD per night

Guest favorite

Apartment in Southington

4.93 out of 5 average rating, 270 reviews

#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*

You're looking at a new construction Mid-Century Modern inspired In-Law Apartment with private access located in a beautiful, quiet neighborhood right in central CT just 1 minute from I-84. Pet fee $25/night per animal The unit features a large backyard with a patio, fire pit and chairs for your enjoyment. Fires must be approved by host. NOTE: THIS AIRBNB IS ONLY SUITABLE FOR UP TO FOR 4 ADULTS AND 1 CHILD. PLEASE ASK ME IF YOU HAVE ANY QUESTIONS OR CONCERNS.

Aug 20 – 27

G$25,770 GYD per night

Guest favorite

Home in Bethlehem

4.97 out of 5 average rating, 262 reviews

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Dec 11 – 18

G$55,772 GYD per night

Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 230 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Oct 13 – 20

G$48,372 GYD 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 13 – 20

G$43,610 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

Mar 13 – 20

G$20,476 GYD per night

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

Mar 14 – 21

G$30,126 GYD 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

G$31,228 GYD per night

Guest favorite

Apartment in Bethlehem

4.94 out of 5 average rating, 226 reviews

Cozy 2nd Floor Suite In Bethlehem CT

Our private 2nd floor suite is fully equipped and easy on the budget. Sleeps 2 in comfort in queen bedroom, spacious living room and well equipped kitchenette. Dedicated workspace. Relax with Wi-Fi, Netflix, Amazon Prime, Sling TV , PBS, Pandora, etc. Free calls anywhere in the US.

Mar 30 – Apr 6

G$26,938 GYD per night

Guest favorite

Home in Newtown

4.98 out of 5 average rating, 132 reviews

Charming Cabin

Charming 2.5 bedroom cabin on quiet lane makes for a peaceful getaway, minutes from great restaurants and cafes in Sandy Hook center and an abundance of nearby hiking trails, lakes, wineries. Nicely situated 1.5 hours from NYC and 2.5 hours from Boston.

Mar 16 – 23

G$45,871 GYD per night