Holiday rentals with a washing machine and dryer in Monterey

4.95 out of 5 average rating, 113 reviews

A rustic cabin is visible in a snowy landscape, surrounded by tall trees and a wooden fence. The cabin is partially obscured by falling snowflakes, creating a serene and tranquil winter scene. Soft snow covers the ground and branches, enhancing the winter atmosphere.

Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

4.99 out of 5 average rating, 351 reviews

Loft in Great Barrington

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.

4.95 out of 5 average rating, 450 reviews

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

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

4.89 out of 5 average rating, 117 reviews

A scenic view of Lake Garfield is framed by lush trees, showcasing a still water surface reflecting the sky. Rolling mountains can be seen in the background, with hints of autumn foliage adding warmth to the landscape under a partly cloudy sky.

Home in Monterey

Hilltop Retreat w Magic View! 15 min Ski Butternut

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

4.95 out of 5 average rating, 154 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Apartment in Great Barrington

A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.

4.91 out of 5 average rating, 128 reviews

King Bed | Patio | 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

4.94 out of 5 average rating, 296 reviews

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

Modern Farm House 5 minutes from Great Barrington

Completely updated with style, this shingled farmhouse combines modern decor with the charm of a country home. Enjoy a spacious, sunny kitchen that connects to a large outdoor patio featuring a fireplace. The cozy living room has a large flat-screen TV for streaming. The first floor includes a bedroom with an attached bathroom & laundry. The second floor suite boasts cathedral ceilings a luxurious jet-powered shower. This home offers a perfect blend of comfort and elegance for your stay!

4.93 out of 5 average rating, 255 reviews

A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.

Cottage in Becket

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

4.95 out of 5 average rating, 294 reviews

A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.

Cabin in Monterey

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

4.96 out of 5 average rating, 290 reviews

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

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

4.97 out of 5 average rating, 145 reviews

A bright bedroom features a spacious bed with neutral bedding, framed by wooden walls and beams. Natural light fills the room through a large window, showcasing a glimpse of the outdoor area. A small side table and a decorative plant complement the simple, serene design.

Cabin in Chatham

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

4.99 out of 5 average rating, 112 reviews

A charming green cottage is surrounded by autumn foliage, featuring a welcoming front porch with white railings. Large windows provide ample natural light, while the overall structure showcases a traditional design with a gabled roof and balcony, nestled in a serene outdoor setting.

Home in Lee

GreenHouse

Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.

Popular amenities for Monterey washing machine and dryer rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a washing machine and dryer

4.97 out of 5 average rating, 290 reviews

A bright living area is highlighted by a slanted ceiling and a pellet stove, offering warmth and comfort. Two black chairs are positioned on a patterned rug, while a sectional sofa provides spacious seating. Natural light filters through a skylight and window adorned with light curtains.

Apartment in Plainfield

Sunny, light filled loft in 1873 Colonial

Apartment in Great Barrington

4.82 out of 5 average rating, 22 reviews

Writer/Reader Retreat: fireplace; near skiing

4.99 out of 5 average rating, 165 reviews

The exterior of a two-story house is displayed, featuring a combination of white siding and a metal roof. An American flag hangs from the porch, surrounded by greenery and flower beds. The front pathway leads to a welcoming porch space.

Apartment in Canaan

West Main

Apartment in Great Barrington

A cozy living room features a light sofa and two armchairs flanking a wooden coffee table. A decorative rug with intricate patterns lies beneath. Natural light filters through multiple bay windows, highlighting the serene and vintage-inspired decor.

5 out of 5 average rating, 134 reviews

Walk Everywhere! | Relax in Easy Elegance!

5 out of 5 average rating, 31 reviews

A welcoming bedroom features a spacious bed dressed in white linens and accented by two bedside tables with lamps. Natural light fills the room through a large window, complemented by a decorative rug with floral patterns on the floor.

Apartment in Lenox

Center of Lenox, cozy Apartment 2-bedroom

Apartment in East Chatham

A tranquil sleeping area features a wooden bed topped with a vibrant patterned quilt. Natural light enters through a window, illuminating the space. A wooden cabinet and a side table with a lamp add functionality, complemented by artwork on the walls showcasing nature scenes.

4.95 out of 5 average rating, 154 reviews

Bennett Abode

4.97 out of 5 average rating, 77 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

4.9 out of 5 average rating, 168 reviews

A welcoming living area is highlighted by natural light streaming in through large windows. A comfortable sectional sofa is paired with two patterned chairs and a round woven coffee table, creating an inviting space for relaxation. A television is positioned on an elegant media console.

Apartment in Craryville

Captain's Quarters at Mickey's Marina

Holiday House Rentals with a Washing Machine and Dryer

4.97 out of 5 average rating, 229 reviews

The exterior of a spacious house is shown, featuring a light-colored facade and a neatly landscaped yard. A winding pathway leads to the entrance, surrounded by lush greenery and colorful flowers. A large window reflects the natural light filtering through the trees.

Home in Millerton

Vacation Home In Millerton

4.88 out of 5 average rating, 169 reviews

A spacious living area is furnished with a light-colored sectional sofa, a cozy armchair, and a coffee table, all arranged around a stone fireplace. Natural light filters through the large windows, enhancing the warm wooden flooring and highlighted by subtle wooden beams.

Home in Hillsdale

Fenced yard, playroom & the Berkshires - $0 fees

4.92 out of 5 average rating, 167 reviews

The front of the house is framed by lush greenery and a vibrant red maple tree. A welcoming red staircase leads to the entrance, while large windows allow natural light to illuminate the interior. The roof is partially covered with clouds, enhancing the outdoor serenity.

Home in Otis

The Pinnacle House at Otis Ridge Ski Area!

4.96 out of 5 average rating, 214 reviews

A tranquil lake scene is presented, with calm waters reflecting greenery from the surrounding trees. A wooden dock extends into the lake, while a selection of houses is visible in the distance, nestled among the landscape.

Home in Copake

Lakefront +pets +skiing +bbq +firepit +games

4.96 out of 5 average rating, 268 reviews

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

Home in Ghent

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

4.99 out of 5 average rating, 115 reviews

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

Home in Great Barrington

Private Home in The Berkshires (New Hot Tub!)

4.95 out of 5 average rating, 170 reviews

The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.

Home in Otis

Idyllic family retreat - spacious lake home,

4.97 out of 5 average rating, 233 reviews

A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.

Home in Lee

Berkshire 4 season home

Holiday condos with a washing machine and dryer

Condo in Litchfield County

A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.

4.93 out of 5 average rating, 30 reviews

Meadow View

A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.

4.95 out of 5 average rating, 63 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

The living area features a comfortable seating arrangement with a dark sofa and a brown chair, complemented by a large mirror. A dining table for four is positioned near a window, allowing natural light to illuminate the space. A soft area rug enhances the room's warmth.

Condo in Great Barrington

5 out of 5 average rating, 9 reviews

Luxury Apt in Downtown Great Barrington

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

Condo in Lenox

4.91 out of 5 average rating, 46 reviews

Spacious 3 bedroom apt in Lenox historic downtown

The exterior of a large, two-story building is showcased against a snowy backdrop, with tall trees partially visible in the foreground. The building features arched entryways and multiple windows, while the sloped ski hill rises in the background, indicating proximity to winter sports.

4.61 out of 5 average rating, 158 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.

5 out of 5 average rating, 4 reviews

Ski Jiminy Peak - 1BD

A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.

Condo in Lenox

4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

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.