Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. Below, you will find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges, and more!
Berkshire Vacation Rentals: Discover Great Barrington, Egremont, Becket, and Adams, MA
Planning your next getaway to the beautiful Berkshires of Western Massachusetts? Discover the perfect home away from home with Berkshire vacation rentals offering convenient access to scenic mountain views, charming New England towns, outdoor adventures, cultural attractions, and year-round entertainment. Whether you are searching for a cozy cabin, a private vacation home, a family-friendly rental, or a peaceful countryside retreat, the Berkshires offer vacation accommodations for every type of traveler.
From the cultural attractions of Great Barrington to the peaceful countryside of Egremont, the natural beauty of Becket, and the historic charm of Adams, Berkshire vacation rentals provide an excellent starting point for exploring everything this popular Massachusetts destination has to offer.
Great Barrington, MA Vacation Rentals
Great Barrington, MA vacation rentals are an excellent choice for travelers who want to experience the best of the Southern Berkshires. Known for its vibrant downtown, independent shops, restaurants, art galleries, and welcoming small-town atmosphere, Great Barrington attracts visitors throughout the year.
Vacation rentals in Great Barrington, Massachusetts, offer access to outdoor recreation, local dining, shopping, and cultural experiences. Visitors can explore the town center, enjoy seasonal festivals, discover local farms, and take scenic drives through the surrounding Berkshire hills.
During warmer months, travelers can enjoy hiking, cycling, swimming, and exploring nearby outdoor attractions. In the fall, colorful foliage transforms the landscape into a spectacular display of New England autumn scenery. Winter visitors can find opportunities for skiing and snowboarding at nearby resorts.
Whether you are planning a romantic weekend, a family vacation, or an extended stay, Great Barrington vacation homes offer a comfortable way to experience the beauty and attractions of Berkshire County.
Egremont, MA Vacation Rentals
If you are looking for a quiet getaway surrounded by natural beauty, Egremont, MA vacation rentals provide an inviting option. This picturesque Berkshire town is known for its rural character, scenic landscapes, peaceful roads, and relaxing countryside atmosphere.
Vacation rentals in Egremont, Massachusetts, are ideal for visitors seeking privacy, outdoor recreation, and a break from busy city life. Travelers can enjoy beautiful mountain scenery, explore the surrounding countryside, and take advantage of the area’s proximity to Great Barrington and other Southern Berkshire destinations.
Egremont is particularly appealing to visitors who enjoy hiking, photography, leaf-peeping, and exploring charming New England communities. Seasonal attractions, local restaurants, art destinations, and outdoor activities are within reach throughout the region.
From secluded vacation houses to comfortable country retreats, Egremont vacation rentals allow visitors to experience a quieter side of the Berkshires while remaining close to popular attractions and amenities.
Becket, MA Vacation Rentals
Becket, MA vacation rentals are perfect for travelers who want to surround themselves with forests, lakes, mountains, and the peaceful beauty of the Central Berkshires. This scenic town offers a relaxing setting for families, couples, outdoor enthusiasts, and anyone looking to escape their everyday routine.
Vacation homes and cabins in Becket, Massachusetts, can provide a comfortable base for enjoying hiking, fishing, boating opportunities, wildlife watching, and scenic drives. The area’s natural surroundings make it especially attractive for travelers who appreciate outdoor adventures and quiet evenings away from crowded tourist destinations.
Becket is also home to the renowned Jacob’s Pillow Dance Festival, which brings visitors to the region for outstanding dance performances and cultural experiences during its season.
Whether you are planning a summer vacation, a fall foliage getaway, or a peaceful winter retreat, Becket vacation rentals offer access to the natural attractions and cultural experiences that make the Berkshires a favorite New England destination.
Adams, MA Vacation Rentals
For travelers interested in mountain adventures, local history, and outdoor recreation, Adams, MA vacation rentals provide an excellent option in Northern Berkshire County. Located near the spectacular Mount Greylock region, Adams offers visitors access to some of the most impressive natural scenery in Massachusetts.
Vacation rentals in Adams, Massachusetts, appeal to hikers, cyclists, families, and travelers looking to explore the Northern Berkshires. Mount Greylock, the highest point in Massachusetts, is a major attraction for outdoor enthusiasts seeking scenic overlooks, hiking trails, and unforgettable mountain views.
Visitors can also explore downtown Adams, discover local history, enjoy regional dining, and take scenic drives through nearby Berkshire communities. Fall is especially popular, when brilliant autumn foliage attracts visitors from across New England and beyond.
Whether you need a comfortable vacation home for a family trip, a convenient rental for a hiking adventure, or a relaxing place to stay while exploring Berkshire County, Adams offers a welcoming destination.
Find Your Perfect Berkshire Vacation Rental
The Berkshires offer something special in every season. Spring brings blooming landscapes and outdoor exploration, summer features festivals and recreational activities, autumn delivers spectacular fall foliage, and winter offers opportunities for snow sports and cozy countryside escapes.
When searching for Berkshire vacation rentals, consider the location, number of bedrooms, available amenities, parking, pet policies, and proximity to your favorite attractions. Options may include private vacation homes, cottages, cabins, country houses, and other accommodations suited to different travel styles and budgets.
Whether you are looking for Great Barrington, MA vacation rentals, Egremont, MA vacation rentals, Becket, MA vacation rentals, or Adams, MA vacation rentals, the Berkshires provide countless opportunities to create a memorable getaway.
Start planning your next Massachusetts vacation and discover why visitors return to the Berkshires for beautiful scenery, small-town charm, outdoor recreation, arts and culture, and relaxing accommodations. Find the right Berkshire vacation rental and enjoy everything this remarkable New England region has to offer.
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Penthouse Apartment On Park Street, Spacious And Clean, Interesting Artwork Throughout, Location Convenient To Local Attractions, Right In Downtown.
Sleeps: 3
Bedrooms: 1
Bathrooms: 2
No Pets
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Cozy Home In The Berkshires, Fenced In Yard! Swim At Windsor Lake, Catch A Concert At Tanglewood Or MassMoca.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Berkshires Family Fun! Kid-Friendly Getaway Near Skiing, Hiking, Museums, Breathtaking Countryside & Mountain Views.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Golf House By Mt Greylock – Walkable Adventures! Large Yard & Cozy Spots To Unwind, Easy Walk To Downtown Adams.
Sleeps: 7
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Winter Berkshires Retreat! Dog Friendly, Hot Tub, Shopping, Snow Sports, Private Canoe, Appalachian Trail Hiking.
Sleeps: 7
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot Jacob’s Pillow, Tanglewood, Norman Rockwell Museum.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Peace And Quiet On The Lake, Close To Tanglewood, Jacobs Pillow, Lee Outlets, Theater, Go Kayaking, concerts, skiing.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Quiet Comfortable 2 Bedroom, 1 Bath Cabin 5 Minute Walk To Swimming And Boating, Screened-In Porch, Just Relax And Have Fun.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Quintessential 6BR Berkshires Lodge, New Pool, Hot Tub, Fire Pit, Ample Yard Space, Ping Pong Table, Enjoy Swimming And Walks.
Sleeps: 14
Bedrooms: 6
Bathrooms: 4
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Becket Home w/3-Season Porch: Walk To Lake Access, Unwind And Embrace Nature, Views Of Lake, Stroll To Sherwood Shoppe.
Sleeps: 7
Bedrooms: 2
Bathrooms: 1
No Pets
Cheshire, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Lakefront Retreat, Breathtaking Year Round Views, Chef’s Dream Kitchen, Golf Cart, Ping Pong & Air Hockey Tables.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Cheshire, MA
Central Berkshire Area
Berkshire Vacation Rentals
19th c. Barn In The Berkshires, Mtn. Views, A Rushing Swimmable Brook, 2 Adjoining Decks, Beautiful Trout Stocked Brook.
Sleeps: 9
Bedrooms: 3
Bathrooms: 2
No Pets
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Bright, Relaxing 2-Story Built In 1843, w/WiFi & Smart TVs, Open Front Porch & Enclosed Back Porch (Shared), Waconah Falls.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Entire Home In Dalton, Perfect Place For A Getaway, Jacob’s Pillow, Hiking Trails, Skiing, Mass MoCA, & The Clark Art Institute.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Dalton, MA
Central Berkshire Area
Berkshire Vacation Rentals
Brooksong, The Perfect Berkshires Getaway, Play Pool, Sip Cocktails At The Antique 1920s Bar, Fire Pit, Wahconah Falls State Park.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Hideaway: Berkshire Home – Village Of Egremont, Close To Hiking, Biking, Shopping, Skiing And The Arts!
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful Period Home In The Berkshires, Two Screened-In Porches, Sits Adjacent To The Appalachian Trail.
Sleeps: 4
Bedrooms: 3
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Kayak On Prospect Lake, Paddle Boards, Swim Dock+! Wonderful, Quiet Retreat. House Is Perfect, Well Appointed, The Lake Is Perfect.
Sleeps: 6
Bedrooms: 5
Bathrooms: 3
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Catamount, Zip Line, Private Setting, Book Now! Porch & Deck, Gas Grill, Short Drive To Many Hiking Trails, 12 Min to GB.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Serene 5BR Retreat, 9-Min To Catamount, Ample Space For Everyone, Hot Tub, Sauna, Indoor Pool, Experience Comfort And Tranquility.
Sleeps: 10
Bedrooms: 5
Bathrooms: 4
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Log Style Home, 4 Miles To Catamount w/Fitness Room, Very Cozy Place To Stay w/The Whole Family, Beautiful And Cozy Oasis.
Sleeps: 7
Bedrooms: 4
Bathrooms: 1
No Pets
Florida, MA
Northern Berkshire Area
Berkshire Vacation Rentals
The Greylock Cabin – True Cabin In The Woods On 30 Acres. Pet-Friendly, Perfect For Your Escape To Tranquility And Privacy.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Great Barrington, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Hotel-Like Balcony Suite, Private Wing & Entry, Ensuite Bath, Walk To Town, Lake, Many Welcoming Touches, Balcony And Beautiful Views.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Contemporary 3BR Home w/Views, Fireplace & Close To Butternut Ski Area, Bsmt. Game Rm, Propane Fire Table On Front Porch.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
2 Bedroom, 1 Bathroom, Riverhouse In The Heart Of The Berkshires, Spectacular Views, Tanglewood, Shakespeare And Co.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Home in Great Barrington, Steps To East Mountain Hiking Trails, Enjoy Sunset Views, Enjoy The Comfort, Charm, And Privacy.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Renovated Private Guest House, Hiking Steps Away w/Beautiful Views Of Mountains & Long Pond, 14 Minutes To Butternut.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Romantic Berkshires Cottage – Stunning Views, Pool, All Seasons are alive w/Beauty, Rolling Hills & Verdant Meadows.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR Cabin w/Large Deck & Yard, Covered Outdoor Dining Area, Visit Berkshire Botanical Gardens, Bidwell House Museum.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
New Home In The Berkshires. Fire Pit, Barrell Hot Tub, Gas Grill, Private & Quiet. Great Location, Close To Stockbridge.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington, Cabin Sleeps 14, Walk To Town, Location Is Wonderful! Beautiful Rural Mountain Views, Perfect Place For Your Family.
Sleeps: 14
Bedrooms: 6
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Zen Riverfront Studio w/Spa Steam Shower, Wood Stove, SKI Catamount/Butternut, Perfect For Couples Or Solo Travelers.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4 Bedroom, 4 Bath Great Barrington Lakeside Getaway With Kayak & Grill, Stunning Water Views And Lakeside Fun, 2 Large Decks.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stunning Renovated Victorian, Blueberry Bushes, Maple Tree, Lawns, Mature Flowers, & Custom Cobblestone, 15 Min Walk From Downtown.
Sleeps: 12
Bedrooms: 5
Bathrooms: 4.5
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Idyllic Retreat; Hot Tub/Sauna, 15 Min From Butternut, Full Gym, Amazing Location Central To All The Berkshires Has To Offer!
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Butternut SKI 4 miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St, Wi-Fi + HOT TUB, WINTER Skiing And Snowboarding.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Gem Of The Berkshires, Mountain View, Short Walk To Lake & Downtown, Breathtaking Views, Screened Porch, Incredibly Clean.
Sleeps: 12
Bedrooms: 5
Bathrooms: 3.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Woodland – Stunning 5BR Home In GB! Ski Butternut – 10 Min Drive, Tanglewood – 24 Min Drive, A Rare Find, Enjoy Fitness Facilities.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tranquil 2BR House w/Woodland & Pasture Views In Great Barrington, Finest Walking & Cycling Routes, Kickback, Relax & Enjoy.
Sleeps: 5
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Large 3 Bedroom House w/WiFi & Air Conditioning In Great Barrington, Relax In Comfort, Inground Pool, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern Escape Near Main Street, Brand-New Bluestone Patio, A Standout Spot To Kick Back, Gather, And Enjoy The Outdoors.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Perfect Nature Haven In Great Barrington, A Spacious, Nature-Surrounded Retreat, Al Fresco Dining On The Deck, A Ping Pong Table.
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
An In-Town Beauty with Late Checkout, 5 Min Stroll To Main St., Close To Tanglewood, Appalachian Trail, Rockwell Museum.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
3BR Victorian Home Within Walking Distance Of Downtown Great Barrington, Built In 1920, Charming Breakfast Nook, Walk To Restaurants.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Vacation Home In Great Barrington, 1 Week Minimum, Tanglewood 20 Min Away, Lovely Boutiques, Screened Porch.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
5BR, 3BA, Sleeps 12 – The Pool Is Open, 2 Fireplaces, 2 Miles From Great Barrington, 5 Min From Ski Butternut.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Secluded Forest Sanctuary • Outdoor Living, Yard, Views | Half Moon By AvantStay, Large Deck, Comfortable Seating, or Grill.
Sleeps: 12
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Great Escape Ski Cottage w/HOT TUB Overlooking The Open Forest View, Festivals & Hiking Trails, Air Hockey Table, Foosball Table.
Sleeps: 16
Bedrooms: 5
Bathrooms: 4
No Pets
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Sunsets On Blue Hill, Newly Renovated Farmhouse, Wrap Around Porch, Hike, Bike Ride, Large Fenced Yard For Children & Pets.
Sleeps: 9
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshires/Great Barrington Chic & Cozy, 4 Bedrooms, Sleeps 10, GB Is Hip & Charming, Great Restaurants & Attractions, Skiing.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Great Barrington, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Premiere Berkshire Country Estate w/Private Pool & Tennis Court – 5 Mins To GB! “The Best Small Town In America.” Notable Charm.
Sleeps: 12
Bedrooms: 4
Bathrooms: 4
No Pets