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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

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A bright entryway features a white wall with hooks for hanging items and a woven basket atop a built-in bench. Light enters through a nearby window, illuminating the space. A simple blue area rug adds a touch of color, and a door leads outside.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

A backyard playset is situated on lush green grass, featuring a swing set with two swings and a slide. A small playhouse with a sloped roof can be seen nearby, surrounded by trees providing a natural and shaded environment.

4.94 out of 5 average rating, 144 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)

A red barn-style house is nestled among autumn trees with vibrant yellow and orange leaves. It features white-framed windows and a covered storage area nearby. The setting conveys a serene environment, inviting guests to enjoy the natural beauty surrounding the property.

Home in Wilmington

4.84 out of 5 average rating, 171 reviews

The Vermont Barn (Mount Snow)

Follow/Tag us on Instagram: thevermontbarn Perfect place to kick back after a long day of hiking, skiing or even just the hustle and bustle of everyday life any time of year! Enjoy our wood stove or soak in the hot tub outside. Our place is very accessible to: hiking, skiing, (Mt. Snow), kayaking, fishing, lake, biking, golfing and small town gems just down the road. Full access to Clubhouse (5 min walk): pools, hot tub, arcade and gym. Great for families, large groups, kid and pet friendly.

Top guest favorite

A functional bathroom is equipped with a shower stall featuring a transparent door, a toilet, and a storage rack. Fresh towels are neatly arranged on the rack, and a colorful rug adds a decorative touch to the tiled floor.

Apartment in Rexford

4.96 out of 5 average rating, 359 reviews

Need a Getaway??

It’s Fall foliage season! Apple picking & hiking, This ideal location is perfect for leaf peeping, visiting family, business travelers, college visits and lots of outdoor recreation. Located about 20 minutes from Saratoga’s city line. This beautiful, quiet and spacious apartment on the 2nd floor overlooks several acres of land. Also, a perfect halfway point between Canada and New York City. We offer complimentary coffee, eggs & pancake mix to cook in the full size kitchen. Pool is heated!

An inviting entryway features warm hardwood flooring and a staircase leading to the upper level. A cozy chair sits beside a small side table. Natural light filters through large windows, which are adorned with soft curtains, illuminating a piano positioned in the corner.

Home in Egremont

4.95 out of 5 average rating, 108 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.

Top guest favorite

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

A charming two-story house features a welcoming porch bordered by colorful flower beds. Blue trim accents the white exterior, highlighting the architectural details. A pathway leads to the entrance, which is framed by a decorative arch and supported by columns.

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

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, 105 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.

A light-filled bathroom features a white countertop with wooden cabinetry below. A large mirror is mounted above the sink, and a framed map adorns the wall. In the corner, a shower enclosure is visible, complemented by slate flooring that adds texture to the space.

Home in Averill Park

4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

An open kitchen and dining area is visible, featuring wooden beams and a modern design. A spacious dining table is surrounded by wooden chairs. Stainless steel appliances complement the kitchen cabinetry, and natural light enters through small windows above.

Cottage in Copake Falls

4.91 out of 5 average rating, 353 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.

Top guest favorite

Natural light filters through large windows into an open hallway featuring warm wood flooring. A wooden staircase leads to the lower level, while a modern kitchen is visible through an archway, accented by a decorative wall element.

Home in Egremont

4.98 out of 5 average rating, 135 reviews

A sunny, quiet chalet beautifully decorated.

Welcome to our modern and sunny chalet nestled in the woods. Located directly across the street from Catamount Mountain Resort for year-round fun. Numerous hiking trails nearby, and Great Barrington’s dining and shopping minutes away. Relax in style and comfort and make unforgettable memories with friends and family. Please not that we do not allow pets.

Top guest favorite

A spacious private porch overlooks a tranquil lake, providing views of a newly built dock on calm waters. Nearby, a grassy area is bordered by trees, adding to the peaceful ambiance of the property.

Home in Averill Park

4.96 out of 5 average rating, 159 reviews

Cozy, peaceful lake house close to Jiminy Peak

My fabulous, peaceful lake house is located on beautiful quiet 3rd Burden Lake complete with a large private porch, dock, a canoe and one kayak. The house has incredible views throughout . Great kayaking, hiking, fishing,close to MASS MOCA. 25 minutes to Troy, Chatham and Albany. Very close to Jimney Peak for skiing in the wintertime.

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

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite

An open floor plan features a dining area with a long wooden table surrounded by colorful chairs. Natural light filters through large windows, illuminating the adjoining living room, which includes a cozy seating arrangement and a modern wood stove. Exposed beams add architectural interest.

Home in Craryville

4.98 out of 5 average rating, 217 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

Top guest favorite

A spiral staircase leads to the upper level, framed by rustic wooden beams. Natural light fills the open living space, where a cozy seating area is arranged around a fireplace. Large glass doors open to the outside, inviting fresh air and scenic views.

5 out of 5 average rating, 58 reviews

The Villa - Industrial Farmhouse with Hot Tub

A charming black exterior cottage is framed by lush green foliage and shrubs. A welcoming entrance with a light-colored door is flanked by two windows, allowing natural light to illuminate the space. A wooden signpost is visible, indicating the property name.

Condo in Hancock

4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

A cozy living area features a deep blue sofa adorned with decorative pillows and a wooden coffee table. Behind the sofa, a white bookshelf is filled with books and decor items, including some vintage pieces and a small lamp, creating an inviting space for relaxation.

Home in Craryville

4.92 out of 5 average rating, 235 reviews

The City Farmers Upstate. Farm house with hot tub

A sunroom features large glass windows offering views of vibrant autumn foliage. A futon couch adorned with colorful cushions is positioned alongside a wooden floor, inviting a relaxing atmosphere. Seasonal leaves are visible on the glass, gently filtering light into the space.

Cottage in Becket

4.65 out of 5 average rating, 164 reviews

A Magical Spot on Little Robin Lake

The exterior showcases a late 1800's Victorian house, featuring a large porch supported by white columns. A driveway is visible alongside the structure, offering access to the yard and surrounding greenery. The house is surrounded by trees, enhancing the neighborhood's charm.

Apartment in Troy

4.91 out of 5 average rating, 174 reviews

Troy-Timeless Rensselaer Victorian

A children's playground area is visible, featuring a wooden play structure beside a sand pit filled with colorful toys. Sunlight filters through the trees, highlighting the nearby pool area which includes lounge chairs and umbrellas.

Home in Wilmington

4.9 out of 5 average rating, 146 reviews

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow

Top guest favorite

A rustic red barn-style home is surrounded by lush greenery, with colorful flowers framing a slate path leading to the entrance. Outdoor seating areas are visible, including a picnic table and lounge chairs, under a vibrant sky painted by sunset hues.

Home in Shaftsbury

4.94 out of 5 average rating, 140 reviews

Converted Vermont Barn on 6.5 acres with hot tub

Family- and pet-friendly home rentals

A spacious bedroom features a light grey bed with simple bedding. A colorful wall art piece adds character to one side, while a desk and chair occupy the other. Natural light filters through the large window, and warm wood flooring complements the overall design.

Vacation home in Hudson

4.85 out of 5 average rating, 128 reviews

Bright and Airy 2 blocks from Warren ST eb

Top guest favorite

A fenced yard is shown with well-maintained grass and colorful flower beds. A grill is placed on a patio area, while a comfortable seating arrangement is visible nearby. In the background, trees and pastureland enhance the serene landscape.

Guesthouse in Stephentown

5 out of 5 average rating, 409 reviews

Dog Friendly Studio

A cozy living area features a light gray sofa adorned with a mix of textured pillows, alongside a round coffee table with a woven tray. Natural light enters through two windows, enhancing the neutral tones of the space.

4.95 out of 5 average rating, 100 reviews

Cozy Modern Farmhouse, a close walk to Warren!

Home in Great Barrington

4.94 out of 5 average rating, 126 reviews

The Hideaway: Berkshire Home - village of Egremont

A charming exterior is visible with a well-maintained pathway leading to a covered porch. The porch features colorful seating options, and greenery surrounds the area, including shrubs and small trees. A flag hangs proudly from the porch, while a mailbox is positioned near the driveway.

Loft in Wilmington

4.91 out of 5 average rating, 199 reviews

Walk to Village/Lake Whitingham

An enclosed three-season veranda features wood-paneled walls and a ceiling adorned with beams. Comfortable seating includes a wicker sofa with cushions, a rocking chair, and various potted plants, creating a serene indoor environment filled with natural light from multiple windows.

Cottage in Craryville

4.91 out of 5 average rating, 524 reviews

Columbia County Getaway - Raspberry Ridge Cottage

A charming guesthouse is set against a backdrop of lush greenery, with a well-maintained lawn and blooming lilac bushes. The structure features a covered porch with a seating area, and there is a connecting garage to the side.

4.9 out of 5 average rating, 282 reviews

Guesthouse close to hiking, shopping and ski!

A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

Beautiful Vermont! (Pet Friendly)

Family-friendly home rentals with a pool

An indoor pool area is highlighted by a wooden ceiling with exposed beams and large windows that invite natural light. A clean, turquoise pool is surrounded by stone flooring, with seating areas and safety equipment visible. The space features a rustic design, enhancing the recreational atmosphere.

Chalet in Wilmington

4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

A clear, inviting pool is surrounded by a neatly manicured lawn and a mix of lounge chairs, set against a backdrop of rolling green hills and trees. The sky is partly cloudy, adding to the peaceful atmosphere of the outdoor space.

Home in Hancock

4.88 out of 5 average rating, 48 reviews

Jiminy Peak Peaceful Home in Berkshires

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

4.88 out of 5 average rating, 313 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

A charming farmhouse exterior is depicted, featuring a welcoming front porch with white railings and a red door. Lush greenery, including tall bushes and white hydrangeas, frames the entrance. Sunlight filters through the trees, enhancing the serene outdoor setting.

Home in Livingston

4.95 out of 5 average rating, 37 reviews

Secluded Farmhouse with pool on 25 private acres

The exterior of the updated Berkshire lake house features a charming red façade with white trim. A spacious porch is visible, with a mix of screened and open areas. Surrounding greenery adds a natural ambiance, while multiple windows allow natural light to fill the interior.

4.99 out of 5 average rating, 86 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

A refreshing pool is framed by a white fence, surrounded by lounge chairs and umbrellas. On the horizon, a serene pond reflects the lush greenery of trees. The area showcases a tranquil outdoor space, inviting relaxation in nature.

4.89 out of 5 average rating, 47 reviews

Queen Suite, Living Room, 2 TVs -Spring House 2

A living room features wideboard flooring and plaster walls, highlighting a decorative fireplace with a tiled surround. Two windows allow natural light to illuminate the space, complemented by a red armchair and a bookshelf filled with books. A cozy sofa and a wooden coffee table complete the setting.

Home in Hillsdale

4.62 out of 5 average rating, 47 reviews

JP Dorr Historic with Pool Hillsdale NY

Family-friendly home rentals with Wifi

A spacious farmhouse is set against a backdrop of lush greenery, featuring a large lawn and a charming swing hanging from a tree. The home's white exterior contrasts with the natural surroundings, creating a serene and inviting outdoor space.

Home in Cummington

4.9 out of 5 average rating, 109 reviews

Beautiful Secluded Country House

Top guest favorite

A charming home is framed by tall trees and lush greenery, with a vibrant lawn in front. The white exterior features multiple windows, allowing natural light to brighten the interior. A clear blue sky with a few clouds completes the tranquil setting.

Home in Stockbridge

4.97 out of 5 average rating, 110 reviews

Greek Revival Farmhouse

A living room is presented with hardwood flooring and natural light from multiple windows. A brown leather sofa with decorative cushions sits across from a modern coffee table. The wall features a large mural of a person near a vintage steam engine, contributing to the unique decor.

4.92 out of 5 average rating, 202 reviews

Hudson New York Grey Victorian

The exterior of a charming two-story home is framed by a black picket fence and neatly manicured shrubbery. The front porch is supported by decorative columns and invites guests into the property. Natural light enhances the inviting facade under a clear blue sky.

4.76 out of 5 average rating, 212 reviews

Cozy Chic Home, Hot Tub, Near Warren St

The bathroom features a walk-in shower with a glass door and a modern showerhead. A round sink is positioned on a granite countertop, complemented by a large mirror above. A towel hangs neatly on a holder, enhancing the functional and clean design.

Apartment in Clifton Park

4.91 out of 5 average rating, 513 reviews

A Place to Relax

Large glass sliding doors reveal a spacious deck with mountain views, framed by wooden accents. The sunlit interior features a comfortable seating area with a patterned chair and neutral-colored sofa, complemented by warm wood flooring and soft rugs.

Home in Hillsdale

4.96 out of 5 average rating, 48 reviews

"The Deck Views Were Breathtaking!"

The cabin is set back from the winding gravel driveway, surrounded by lush green grass and trees. Brightly colored autumn foliage adds a touch of warmth against the rustic brick exterior and red roof. The peaceful atmosphere is enhanced by natural surroundings.

Home in Wilmington

4.84 out of 5 average rating, 87 reviews

Secluded cabin on brook near skiing and lakes

An open living space features a kitchen area with modern appliances and white cabinetry. A round wooden table is surrounded by white chairs, while two wicker armchairs invite relaxation. Wood beams add character to the ceiling, enhancing the warm, rustic environment.

Loft in Mechanicville

4.82 out of 5 average rating, 417 reviews

★Chic Loft w/ Indoor Pergola & Lots of Space

Quick stats about family-friendly rentals near Jiminy Peak Mountain Resort

Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
1.3K reviews
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi

Destinations to explore