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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Top guest favorite

Home in Milford

4.94 out of 5 average rating, 137 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Guest favorite

Home in Millerton

4.92 out of 5 average rating, 399 reviews

Mountaintop Skyloft

This glorious Silver Mountain SKYLOFT is perfect for a getaway; equipped with hi-speed WiFi (429 mbps) and 60" HD TV. Huge private deck amid the treetops, with 100's of acres of tranquility and privacy Enjoy a romantic evening by the wood burning fire. Jupiter and Mars in the Spring sky. Lots of trails for hiking. Local gourmet food bistro & organic farm market nearby. Just 7 miles from Millerton antiques and cafe. Pets welcome- extra $65/pet/stay (Sofa bed @$99/person/night after 2 )

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 267 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Superhost

Cottage in Branford

4.86 out of 5 average rating, 222 reviews

Cozy Home In Short Beach Community

A cozy home in a beach community which is in a central location with easy access to many outdoor activities(private beach access) & local restaurants. The location is also 5 minutes from the Branford Train Station, Stony Creek Brewery, Branford's town center. New Haven the home of Yale University, Yale Hospital and other colleges in the New Haven area are a short drive The house is across the street from Farm River. across the street in opposite direction is a short walk to Johnsons beach.

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Guest favorite

Home in Morris

4.87 out of 5 average rating, 149 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.

Superhost

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Top guest favorite

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guest favorite

Home in Litchfield

4.98 out of 5 average rating, 232 reviews

Storybook Cape...HOST & Co.

A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where you can enjoy antiquing, dining, shopping, and relaxing in the picturesque town center. If hiking and outdoor activities are more your thing we are also minutes from White Memorial Foundation and Topsmead National Forest is right around the corner. Mohawk Mountain Ski Area is 12 miles away.

Guest favorite

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 296 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Top guest favorite

Cottage in Staatsburg

4.91 out of 5 average rating, 193 reviews

Charming Creek side Getaway 3.5 mi. from Omega

Nestled in a creek side hollow, this private and cozy cottage offers a welcoming space to relax and refresh in. The house has a charm all its own, featuring beautiful furnished rooms with the accent on comfortable. Combine that with the creek side setting without another visible house from the property and it truly feels like a "nature's getaway".

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What guests are saying

Farmington River Carriage House Pleasant Valley CT

4.89 out of 5 average rating, 97 reviews5 months ago

We had a beautiful, peaceful stay at Bruce and Cheryl's guest home. The space was perfect for my toddler to run around in the yard, the accomodations were cozy and quiet, and our hosts were very gracious. Bruce built us a fire in the fire pit overlooking the river one evening. It was incredibly beautiful! If you have an EV, there is a convenient Tesla charger on site. The property is only a short walk away from a state park with miles of hiking trails. We would definitely like to go back for another stay!

Guesthouse in Barkhamsted

What guests are saying

Cozy Candlewood Isle Cottage

4.81 out of 5 average rating, 77 reviews2 months ago

This was the perfect weekend getaway - the house is cozy and beautiful, the neighborhood was lovely, had incredible views and offered so much to see and do. The fireplace was amazing, great kitchen with everything you need and the host was highly communicative and helpful. I can't wait to return!

Home in New Fairfield

What guests are saying

Town. Walk to the lake, enjoy all.

4.86 out of 5 average rating, 105 reviews8 months ago

I love this AirBnB and hope to use it again next time I am working in the area or visit with my husband and our baby. It is the perfect location if you want to be in the Sharon, Lakeville, Salisbury area. You can walk to a handful of great locations. Oh and the towels are oddly the softest I've ever felt! What's the secret?! We laughed about it all weekend. Beautiful, perfect spot! We have a brief check-in snafu/delay (I didn't receive the welcome info to sort out where the key was) but Pierce got us the information as soon as we connected. No other issues whatsoever, I absolutely recommend!

Apartment in Salisbury

What guests are saying

Cozy 2nd Floor Suite In Bethlehem CT

4.94 out of 5 average rating, 249 reviews3 months ago

Our Christmas stay at Janice’s was perfect! My partner and I needed a place to stay while visiting family for holidays. The suite was very clean and cozy. We really enjoyed the not one but TWO gas fireplaces! Janice also had a small artificial Christmas tree in the living room which made it so festive and the perfect place for us to rest and watch Christmas movies after days with family. The bed was comfortable and had four pillows with extras in the closet along with extra blankets, an iron and board. Janice was flexible with our check in time and very friendly. The only negative we could think of was that we’d love to have a full kitchen and the suite just has a kitchenette with mini fridge, microwave and toaster oven, but we knew that from the description and it was fine for a short stay. We’d love to stay here again. Really perfect for this trip.

Apartment in Bethlehem

What guests are saying

Stunning Views, Light and Open - The Beech House

5 out of 5 average rating, 112 reviews1 week ago

We had the most peaceful and rejuvenating stay here! The views were absolutely breathtaking — waking up to such natural beauty each morning was pure bliss. The entire place had a calming, serene atmosphere that made it so easy to unwind and truly relax. My pup loved the large yard. What made the stay even more special were the thoughtful little gifts left for us — such a sweet and personal touch that really made us feel welcome and cared for. Highly recommend for anyone looking to escape, recharge, and soak in some stunning scenery. Can’t wait to come back! Thanks again Sarah and Jonathan

Home in Millbrook

What guests are saying

Cozy Little Cottage

4.85 out of 5 average rating, 169 reviews1 week ago

My daughter and I loved our stay so much. The setting is so beautiful and peaceful. I loved listening to all the bird song and my daughter loved the fish! Such a cozy, comfortable home. We loved our relaxing time here. Gabriele is a fabulous host, so responsive and so kind. Thank you!!

Cottage in Canaan