Family-friendly holiday rentals in North Adams

Place to stay in North Adams

A cozy bedroom features a spacious bed draped in a soft, dark blanket. The walls are adorned with a captivating array of framed artwork, showcasing various styles. A bedside table holds a lamp, and a curtain partially covers a window, allowing natural light to filter in.

4.93 out of 5 average rating, 276 reviews

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

Indoor spacesKitchenSleep quality

4.93 out of 5 average rating, 176 reviews

Loft in North Adams

Location, location, location!

This 1600 sqft loft apartment is located at the corner of the two most happening streets of Downtown North Adams - Main Street & Eagle Street. Quintessential stores and restaurants are at your footstep, while MASS MoCA is within walking distance. The apartment has high ceilings, exposed beams, and was furnished in 2021 with an energetic vibe. Whether you intend to work-from-home or just relax, the turn-key operation and well-stocked loft apartment are designed to enhance your experience in town.

FamilyKitchenHospitality

Guest suite in Williamstown

A serene bedroom showcases a queen bed adorned with light bedding, set against calming green walls. A light-colored armoire and a small side table are visible, while natural light enters the room, creating a soft ambiance. A plush pillow is placed at the head of the bed.

4.96 out of 5 average rating, 267 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

FamilyKitchenWi-Fi

4.86 out of 5 average rating, 118 reviews

A charming exterior view of the home shows a modest structure with a gray shingle facade and green windows. A wooden deck extends toward a seating area, while a pathway of stepping stones leads through the yard. Lush greenery is visible in the background.

Home in Clarksburg

New & Cozy~Near MoCa~Deck~River

Retreat to the lovely 2BR 1Bath oasis nestled in the charming city of North Adams, MA. Escape the big-city crowds by taking in the beautiful natural surroundings from the deck while being less than 5 mins from the famous MoCa museum, exciting attractions, and scenic landmarks. A haven of relaxation awaits you. ✔ 2 Comfortable Bedrooms (Sleeps 4) ✔ Cozy Living Area ✔ Fully Equipped Kitchen ✔ Private Deck with Seating ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

Indoor spacesKitchenAccess

The exterior of a restored Victorian home is showcased, featuring a vibrant color palette and decorative architectural details. Lush greenery surrounds the house, with ornamental plants framing the entrance and providing a welcoming atmosphere. A front porch is visible, inviting relaxation.

4.94 out of 5 average rating, 285 reviews

Mountain View Victorian Retreat by Evergreen Home

Evergreen Home Vacation Rentals invites you to this beautifully restored Victorian, just a 5-minute walk to downtown. Located near MCLA and Mass MoCA, and 10 minutes from Williamstown, this spacious home offers stunning mountain views from the deck. Perfect for every season: enjoy Jiminy Peak skiing (30 mins), Vermont trails, or summer kayaking and fall foliage. Whether you’re here for art, culture, or a quiet retreat, this lovely home is your ideal Berkshire base.

FamilyKitchenWalkability

A view of the urban cabin surrounded by greenery, showing the rolling hills of the Hoosac Range in the background. The cabin is complemented by lush foliage and trees, creating a serene atmosphere, while the townscape can be seen in the distance.

4.88 out of 5 average rating, 112 reviews

Colorful Urban Cabin Steps from Mass MoCA

Enjoy the best of the Berkshires from this charming urban cabin: easy access on foot to North Adams' restaurants, bars, and Mass MoCA, plus panoramic views of the Hoosac Range from the front porch and backyard. Easy drives to hiking, swimming, skiing and the rich cultural amenities of the region. Please note: the ceiling is a little low in a few places. Anyone 6'3 or taller will want to watch their head in a few places, including getting in and out of the shower.

KitchenIndoor spacesSkiing

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.

4.99 out of 5 average rating, 216 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

KitchenFamilyAccess

The charming exterior of a Victorian home is framed by vibrant autumn foliage. A welcoming porch extends across the front, featuring a red door and large windows that create a bright atmosphere. The roof is adorned with traditional shingles, contributing to its historic character.

4.96 out of 5 average rating, 728 reviews

Steps to MoCA: 2bd + SAUNA!

A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

KitchenFamilyLocation

4.97 out of 5 average rating, 344 reviews

A cozy kitchen area features a wooden dining table set with a small flower vase. Two white chairs are positioned around it, with a colorful rug underneath. Light wooden paneling and a window allow natural light to brighten the space, enhancing the welcoming ambiance.

Barn in Williamstown

Cozy barn apartment on the river

Private converted first floor barn apartment next to the Green River. Comfortable with unique furnishings and back door that opens to a riverfront covered patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper, tri-fold floor mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. It is on our property with a shared driveway.

KitchenFamilyCleanliness

The light-filled living room features a comfortable gray couch with decorative pillows, a vintage coffee table, and an eclectic mix of artwork on the walls. A television is positioned on a wooden stand, and diverse seating options are provided by antique chairs and a small dining table.

4.97 out of 5 average rating, 194 reviews

Charming Art Filled Apartment

Charming and quirky, this 2nd floor apartment in a 120 year old house is decorated with art and antiques, like the living museum of an eccentric friend. Or a mini theme park for the mind. We are just blocks from downtown North Adams, on the main road into town. It’s literally a 2 minute drive to MASS MOCA, or a ten minute walk. Dogs are always welcome!

FamilyKitchenComfort

A spacious green yard is surrounded by trees, featuring blooming vegetation. A gravel patio is visible to one side, equipped with outdoor seating and a grill. In the background, a distant view of mountains can be seen beyond the residential structures.

4.99 out of 5 average rating, 154 reviews

Whiteley Hideaway- walk to Mass MoCA and Downtown

You will love being tucked away in this bright spacious home! Nestled in quiet neighborhood with a gorgeous outdoor kitchen and a distant view of Mt Greylock, large yard, front and back porches for sitting, off street parking for 2 cars and....Only 4/10 mile to Mass MoCA! Come home after a fun filled day and enjoy a glass of wine by the fire!

FamilyIndoor spacesBathroom

A balcony deck is depicted with two blue Adirondack chairs facing a small round table. A floral centerpiece is placed on the table, which is accompanied by two glasses. The area is surrounded by lush green trees, creating a serene atmosphere.

4.98 out of 5 average rating, 143 reviews

Historic Victorian - Entire 3rd floor

Welcome to our historic home in the heart of North Adams. You will have the entire 3rd floor apartment to yourself, which includes a large balcony deck with great views, full kitchen, bathroom, living room with TV, and bedroom. The third floor is separate from the main house and has two private entrances. Three driveway parking spots available.

Indoor spacesFamilyOutdoor spaces

Popular amenities for North Adams family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.94 out of 5 average rating, 189 reviews

Berkshire Mountain Top Chalet

KitchenIndoor spacesAccess

Superhost

The inviting living area features intricate wood detailing and an ornamental ceiling. Two comfortable armchairs flank a round marble coffee table, positioned over a traditional area rug. A decorative fireplace and a flat-screen TV offer cozy amenities, while natural light fills the space through nearby windows.

4.87 out of 5 average rating, 205 reviews

Art House With Hot Tub Near MASS MoCA

FamilyIndoor spacesAmenities

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

4.87 out of 5 average rating, 119 reviews

The House of Pi

KitchenIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 131 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

FamilyKitchenBackyard

4.96 out of 5 average rating, 204 reviews

The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.

Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 397 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

Indoor spacesKitchenBackyard

4.95 out of 5 average rating, 152 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

FamilyKitchenBathroom

4.98 out of 5 average rating, 777 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Indoor spacesFamilyLong stay

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 219 reviews

Guesthouse in Cummington

Cozy Hilltown Cottage

FamilyKitchenParking

4.87 out of 5 average rating, 128 reviews

A historic Victorian home is presented with multiple levels and large, decorative windows. The white exterior is complemented by a wraparound porch adorned with railings. Lush greenery surrounds the house, enhancing the inviting front entrance, while flowering shrubs add a touch of color to the landscape.

Guest suite in Adams

Quaint Suite in Center of Adams

KitchenIndoor spacesHeating

The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.

4.91 out of 5 average rating, 505 reviews

Private guest apartment. One block from downtown.

KitchenIndoor spacesAccuracy

A vibrant living room features a plush pink sofa, accented by colorful throw pillows. Two comfortable armchairs provide additional seating. A wooden coffee table is centered on a patterned area rug, surrounded by natural wood flooring. Wall-mounted lights enhance the bright and inviting atmosphere.

4.89 out of 5 average rating, 155 reviews

Central Haus (Cozy Group Getaway)

KitchenIndoor spacesBarbecue

4.92 out of 5 average rating, 226 reviews

A sunlit sleeping area features large windows allowing natural light to fill the space. A spacious bed sits covered with a textured blanket, complemented by a small side table with flowers. Sheer curtains frame the windows, blending the indoor space with views of the surrounding nature.

Tiny home in Cambridge

Runamuk Farm

KitchenFamilySolo travel

Place to stay in Stratton

The A-frame house is framed by tall trees, featuring large triangular windows that enhance natural light. A wooden deck extends to a seating area with two rocking chairs and a picnic table. A person walks their dog along the path leading to the entrance.

4.99 out of 5 average rating, 218 reviews

The Chal-A-Frame Vermont

KitchenIndoor spacesBackyard

4.99 out of 5 average rating, 137 reviews

A bright living area is highlighted by large windows offering expansive mountain views. A colorful abstract artwork hangs against a brick wall, framed by a green houseplant. A wooden coffee table sits atop a patterned rug, complemented by a cozy sofa and a wall-mounted TV.

Cottage in Williamstown

Artistic Nature Cottage

FamilyIndoor spacesBathroom

4.93 out of 5 average rating, 136 reviews

The unique dome-shaped structure is composed of iron and cement, surrounded by lush greenery. Large windows create a bright and airy atmosphere, while the greenhouse-style addition at the front enhances the connection to nature.

Dome in Bennington

5BR Rustic Mountain Sanctuary Dome Home

Indoor spacesFamilyLong stay

Family-friendly home rentals with a pool

Guesthouse in Williamstown

A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.

4.93 out of 5 average rating, 259 reviews

Private Guesthouse in Williamstown

KitchenIndoor spacesQuiet

4.89 out of 5 average rating, 378 reviews

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.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

KitchenIndoor spacesComfort

4.95 out of 5 average rating, 169 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

KitchenFamilyParks

4.92 out of 5 average rating, 106 reviews

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

FamilyIndoor spacesWi-Fi

4.97 out of 5 average rating, 122 reviews

A wrought-iron archway frames the view of a tranquil lake, leading toward a wooden dock that extends into the water. Flower pots adorned with vibrant blooms sit atop a stone wall, enhancing the serene lakeside atmosphere.

Home in Saratoga Springs

Waterfront Saratoga Lake home!- Pool, dock, kayak

FamilyIndoor spacesCheck-in

4.83 out of 5 average rating, 107 reviews

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

FamilyKitchenSkiing

4.89 out of 5 average rating, 180 reviews

A cozy living area features a leather sectional sofa adorned with patterned throw pillows. Natural light flows through large windows, illuminating warm wood paneling and a brick fireplace. A game table stands nearby, accompanied by rustic decor and hardwood flooring.

Home in Wilmington

Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow

Indoor spacesFamilyComfort