Family-friendly holiday rentals in Goshen

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Goshen

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

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Guest favourite

Home in Millerton

4.92 out of 5 average rating, 396 reviews

Mountaintop Skyloft and SNOW

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 favourite

Home in Ancram

4.99 out of 5 average rating, 173 reviews

Snuggle by the Fireplace Ski/Snowboard Pets Ok!

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Superhost

Home in Otis

4.94 out of 5 average rating, 142 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

Superhost

Home in Egremont

4.95 out of 5 average rating, 107 reviews

Bucolic Berkshires House

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

Superhost

Home in New Milford

4.89 out of 5 average rating, 187 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.

Guest favourite

Home in Sheffield

4.9 out of 5 average rating, 113 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favourite

Cabin in Hillsdale

4.89 out of 5 average rating, 99 reviews

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Guest favourite

Home in New Fairfield

4.92 out of 5 average rating, 109 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 favourite

Home in Litchfield

4.98 out of 5 average rating, 228 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 favourite

Cottage in New Fairfield

4.94 out of 5 average rating, 266 reviews

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

Charming waterfront 4 Bedroom / 2 BA house on Candlewood lake with private dock and toys. Lake living at its best out your back door. Great yard and updated house for hosting family & friends. Turn Key vacation ~75 minutes / 60 miles from NYC. Screened in Porch, Backyard Patio w/ firepit, Grill and more. Well stocked house with full kitchen, TONS of movies & entertainment, and more.

Guest favourite

Cottage in Copake Falls

4.91 out of 5 average rating, 345 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Superhost

Cabin in Otis

4.86 out of 5 average rating, 413 reviews

Cozy cabin in the Berkshires

UPDATE: We have broadband!! Cozy and peaceful Scandinavian inspired post and beam cabin. simple, unfussy. Near many wonderful Berkshires activities. Minutes from Jacobs Pillow, lakes, ponds, hiking, biking, skiing. amazing local food and farms. Perfect country retreat for a weekend, a week or the whole month. sleeps up to 4.