Family-friendly vacation rentals in Egremont

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Top-rated family-friendly rentals in Egremont

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

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Guest favorite

A charming two-story country cottage is shown, featuring natural wood siding and a welcoming entrance. A stone pathway leads to the front door, bordered by a manicured lawn and mature trees, embodying a peaceful rural setting.

Cottage in Craryville

4.91 out of 5 average rating, 541 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

Top guest favorite

An exterior view of the renovated red barn features a sloped roof and white-trimmed windows. Two white Adirondack chairs adorned with pink cushions are positioned on the grass, under the shade of a nearby tree, providing a cozy outdoor seating area.

Loft in Great Barrington

4.99 out of 5 average rating, 334 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Guest favorite

A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.

Chalet in Otis

4.95 out of 5 average rating, 421 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favorite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 358 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite

A well-lit bedroom features a spacious bed with crisp white bedding and a decorative throw. A sliding glass door leads to a patio area, framed by light curtains. Minimalist shelving holds decorative items, and a fan is positioned beside the bed.

Guest suite in Great Barrington

4.98 out of 5 average rating, 112 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Guest favorite

A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.

Cabin in Hillsdale

4.9 out of 5 average rating, 107 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 favorite

The exterior of the house is showcased, featuring a red wood siding that complements the natural surroundings. Lush green grass and trees frame the property, while a hint of blooming foliage adds subtle color. The structure includes multiple sections with a sloped roof and chimney.

Home in Egremont

4.9 out of 5 average rating, 126 reviews

Beautiful Period Home in the Berkshires

Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house combines the charm of the antique with all the modern conveniences including two screened-in porches. Conveniently located five minutes from Gt. Barrington, MA and 25 minutes from Stockbridge, Tanglewood, and Hudson, NY. The property also sits adjacent to the Appalachian Trail with plenty of local options for hiking and skiing.

Guest favorite

A charming shingled farmhouse is surrounded by lush greenery and colorful flowering plants. The stone walkway leads to the welcoming front porch. Tall trees provide shade, while a skylight enhances the natural lighting on the upper level.

Home in Egremont

4.94 out of 5 average rating, 281 reviews

Modern Farm House 5 minutes from Great Barrington

Completely renovated with absolute style, this shingled farmhouse boasts clean modern decor with the architectural charm of a country home. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace. Cozy living room with large flat screen television for streaming Netflix & Amazon. First floor bedroom with bathroom & laundry. The second floor master suite has cathedral ceilings & a jet powered glass shower.

Guest favorite

The living room features a combination of seating, including a red sofa and patterned chairs, arranged around a coffee table. Natural light flows through two windows, and a small TV is mounted on the wall. A stone fireplace adds rustic charm to the warm wood-paneled space.

Cabin in Hillsdale

4.8 out of 5 average rating, 321 reviews

Rustic, peaceful and affordable cabin

This cabin is in a lovely, peaceful setting. Cozy and private, it has enough room for a big family gathering. The cabin has almost 10 acres of privacy (but with next door neighbors in sight) and lots of outdoor space, but is very close to all of the Berkshires attractions. Skiing at Catamount and Butternut, hiking at Bash Bish and Mount Greylock, biking and swimming at Taconic State Park and its rail trail all close by.

Guest favorite

A charming home is set on a raised stone foundation, featuring a bright blue front door that adds a pop of color. Lush green grass surrounds the property, complemented by a stone walkway leading to the entrance. Mature trees and yellow forsythia bushes provide a natural backdrop.

Home in Great Barrington

4.95 out of 5 average rating, 128 reviews

The Hideaway: Berkshire Home - village of Egremont

**NEW KITCHEN APRIL 2025!!**. Welcome to our family's home in the village of Egremont (part of Great Barrington). Both the house and property are open and inviting! You'll feel relaxed the minute you arrive. The kitchen is equipped with everything you should need for your stay. Our house is perfect for just a couple or a group. Please reach out to me with any questions!

Top guest favorite

A bright living area features large floor-to-ceiling windows, allowing natural light to fill the space. A brown leather sofa is paired with a clear acrylic coffee table, while plants add a touch of greenery. Warm lamps provide additional lighting, enhancing the cozy ambiance.

Loft in East Nassau

4.99 out of 5 average rating, 185 reviews

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Guest favorite

A charming cottage is nestled among lush greenery, featuring a large wooden deck that invites relaxation. Sunlight filters through trees, and the inviting front porch is accessible from the yard, offering a seamless transition between indoor and outdoor spaces.

Cottage in Copake Falls

4.91 out of 5 average rating, 358 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.