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Family-Friendly rentals near Jiminy Peak Mountain Resort

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Top-rated family-friendly rentals near Jiminy Peak Mountain Resort

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Guest favorite
An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

4.95 out of 5 average rating, 275 reviews
Top guest favorite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

4.97 out of 5 average rating, 107 reviews
Top guest favorite
A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.
Townhouse in Hancock

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

4.92 out of 5 average rating, 115 reviews
Top guest favorite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

4.95 out of 5 average rating, 232 reviews
Top guest favorite
The entrance to a Hobbit house is framed by lush greenery and natural stone. A curved, grassy roof merges with the surrounding trees, while a stone pathway leads to the large wooden door. Decorative lanterns are positioned above the entrance, enhancing the rustic charm.
Earthen home in West Sand Lake

The Hobbit House at June Farms

Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

4.97 out of 5 average rating, 255 reviews
Guest favorite
An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.
Guest suite in Hancock

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

4.82 out of 5 average rating, 212 reviews
Top guest favorite
Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

4.99 out of 5 average rating, 318 reviews
Top guest favorite
A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.
Apartment in Petersburg

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

4.9 out of 5 average rating, 232 reviews
Guest favorite
A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.
Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

4.83 out of 5 average rating, 109 reviews
Guest favorite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

4.93 out of 5 average rating, 108 reviews
Top guest favorite
A charming Victorian home is showcased at dusk, with bright windows illuminating the exterior. The wraparound porch features decorative railings and flower planters, complementing the elegant architectural details. The two-story structure is framed by a darkening sky, enhancing its inviting presence in the neighborhood.
Home in Adams

Beautiful Victorian. The heart of the Berkshires.

The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.

4.91 out of 5 average rating, 149 reviews
Top guest favorite
A spacious living room features a dark sectional sofa and a wooden coffee table on a light rug. A modern armchair is positioned nearby, with a floor lamp providing light. Large windows allow natural light and offer views of the surrounding trees.
Home in Lanesborough

Tranquil mid-century modern Berkshires retreat

We love the Scandi House because of its simplicity, openness, warmth, comfort, trees, space, privacy, and convenience. We enjoy this Berkshires retreat for its close proximity to all what Berkshires has to offer in music, arts, and outdoor activities. Most of all, we treasure the tranquility and each other when we are here at the house in the woods.

4.99 out of 5 average rating, 135 reviews

Popular amenities for family-friendly rentals near Jiminy Peak Mountain Resort

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield

Hidden Oasis in the Mountains by Evergreen Home

4.97 out of 5 average rating, 156 reviews
Guest favorite
A spacious mountain lodge is depicted, featuring a striking stone chimney and expansive decks. Large windows frame the scenic landscape, while lush green grass surrounds the building. The warm tones of the log exterior harmonize with the natural setting, inviting outdoor relaxation.
Apartment in North Adams

Berkshire Mountain Top Chalet

4.94 out of 5 average rating, 192 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

4.88 out of 5 average rating, 121 reviews
Top guest favorite
Tiny home in Wilmington

Beautiful Timber Frame Retreat

5.0 out of 5 average rating, 402 reviews
Top guest favorite
The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.
Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

4.98 out of 5 average rating, 134 reviews
Top guest favorite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

4.99 out of 5 average rating, 377 reviews
Top guest favorite
The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.
Home in Monterey

Jaw dropping mountain & lake views

4.96 out of 5 average rating, 309 reviews
Guest favorite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

4.94 out of 5 average rating, 134 reviews

Family- and pet-friendly home rentals

Top guest favorite
A mid-century A-frame house is set within a lush landscape, surrounded by trees displaying autumn colors. A spacious driveway leads to the entrance, and a large deck with railings extends along the front, offering an inviting outdoor space.
Chalet in Averill Park

A Hidden Sparrow

4.93 out of 5 average rating, 102 reviews
Top guest favorite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton

Brooksong, the perfect Berkshires getaway

4.93 out of 5 average rating, 211 reviews
Top guest favorite
A charming two-story red house is surrounded by lush greenery and colorful flowering plants. Sturdy steps lead up to the entrance, framed by vibrant shrubs and hydrangeas, creating a welcoming outdoor area that blends naturally with the landscape.
Home in New Lebanon

The old sawmill from 1771

4.99 out of 5 average rating, 385 reviews
Superhost
A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.
Home in Cheshire

19th c. Barn in The Berkshires

4.86 out of 5 average rating, 228 reviews
Top guest favorite
A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.
Cottage in Williamstown

Cute Cozy Comfy Cottage in the Berkshires

4.9 out of 5 average rating, 210 reviews
Guest favorite
The exterior of a two-story house is visible, featuring white siding and dark green shutters. A lush yard with flowering plants surrounds the home, while trees provide a natural backdrop. Windows showcase the rooms within, blending the structure harmoniously with the landscape.
Apartment in Stephentown

Cozy 2-Bedroom Vacation Apartment

4.99 out of 5 average rating, 110 reviews
Guest favorite
A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.
Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

4.85 out of 5 average rating, 300 reviews
Top guest favorite
A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.
Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

4.94 out of 5 average rating, 207 reviews

Family-friendly home rentals with a pool

Top guest favorite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

4.99 out of 5 average rating, 101 reviews
Top guest favorite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

4.9 out of 5 average rating, 239 reviews
Top guest favorite
Cottage in West Sand Lake

Cozy Cottage with pool and walk to lake

4.99 out of 5 average rating, 130 reviews
Top guest favorite
Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

5.0 out of 5 average rating, 131 reviews
Guest favorite
Home in Hancock

Family Lodge at Jiminy Peak - Pools & Adventure

4.95 out of 5 average rating, 58 reviews
Guest favorite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock

Jiminy Peak Country Inn - ski in/out condo MT view

4.92 out of 5 average rating, 85 reviews
Top guest favorite
Condo in Hancock

3BR @ Jiminy Peak | 4-Season Berkshires Retreat

5.0 out of 5 average rating, 12 reviews
Guest favorite
A view from the condo showcases snow-covered slopes leading up to the mountain, with ski lifts operating in the distance. The landscape is framed by the rustic stone chimney of the adjacent building, creating a serene winter scene.
Apartment in Hancock

Ski-InSki-Out Loft Lift&MT.Views

4.95 out of 5 average rating, 55 reviews

Family-friendly home rentals with Wifi

Top guest favorite
A hammock is suspended between two large trees, offering a serene spot to relax by the water. Below, colorful kayaks rest on the grassy shore, framing the edge of Glass Lake, which reflects the surrounding greenery and blue sky.
Home in Averill Park

Lake House in Averill Park, NY

4.97 out of 5 average rating, 202 reviews
Top guest favorite
A spacious deck is shown with lightly stained wooden flooring and several wooden chairs arranged in a circle. In the background, a large two-story home is visible, surrounded by greenery and trees under a clear blue sky.
Home in Averill Park

Lakefront Retreat: Bald Eagles & Huge Windows

5.0 out of 5 average rating, 112 reviews
Guest favorite
A charming stone building is surrounded by lush greenery and colorful flowers, including pink and white blossoms. The sign, featuring 'Stone School Cottage,' is prominently displayed. Large windows indicate a bright interior. The setting offers a peaceful and inviting entrance to the accommodation.
Cottage in Lanesborough

Stone School Cottage

4.93 out of 5 average rating, 264 reviews
Guest favorite
Home in Hancock

Mountainside Condo w/ Private Access To Ski Slope

5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Hancock

Condo on the mountain

4.96 out of 5 average rating, 27 reviews
Superhost
An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.
Apartment in Hancock

Mountainside Condo Ski on/off

4.84 out of 5 average rating, 44 reviews
Guest favorite
A welcoming family room is presented, featuring two black leather sofas adorned with throw pillows. A wooden coffee table sits in the center, surrounded by a soft area rug. A flat-screen TV is mounted above a wood-burning fireplace, with natural light streaming in through multiple windows.
Townhouse in Hancock

Newly Renovated Mountainside Townhome, Jiminy Peak

4.92 out of 5 average rating, 39 reviews
Top guest favorite
A charming two-story home is set amidst lush greenery, featuring a spacious front porch with seating. The house is flanked by trees, and a large lawn is visible in front, complemented by a gravel driveway leading towards an attached garage.
Home in Lanesborough

Berkshire Mountain House

5.0 out of 5 average rating, 42 reviews

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