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!
Luxury 5 Bedroom House On Private 47 Acre Oasis, Heated Pool & Pond Views, Sleeps 10
Spend your private getaway in this Immaculate contemporary home on 47 acres with 3 acre pond, heated gunite pool and private hiking trails. Sunfilled living room with 20 foot ceilings opens to the dining area and eat-in kitchen. Spacious first floor primary suite. Two stories of large outdoor decks for entertaining with views to the pond, pool and beautifully manicured grounds. Four additional beautifully appointed guest rooms. Fully finished lower level with in law suite and fitness area. Quick & easy “back road” access to Tanglewood. Minutes to Mass Pike and Berkshires best attractions!
Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
A Beautiful Place To Enjoy The
Beautiful Berkshires!
Sleeps: 14
Bedrooms: 7
Bathrooms: 3.5
No Pets
Alford, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Dream Land 10 Minutes From Town
2 Story Berkshire Farmhouse.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Alford, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Studio Loft In The Berkshires, Overlooking
The Farm & Mountains.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Alford, MA
Southern Berkshire Area
Berkshire Vacation Rentals
5 Bedroom 3.5 Bath Home
Overlooking Alford Brook On 15 Acres.
Sleeps: 8
Bedrooms: 5
Bathrooms: 3.5
No Pets
Alford, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Case Mill-Secluded Berkshire, Pond,
Farmhouse, Mill, Waterfall, 28 Acres.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Alford, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful 7 Bedroom, 4.5 Bath
Berkshire Farm House, 160+ Acres.
Sleeps: 16
Bedrooms: 7
Bathrooms: 4.5
Pets Considered
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Private Lake Cottage Near Jacob’s
Pillow And Tanglewood.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Serene, Private Waterfront House,
Perfect Summer Retreat!
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Elegant Country House With Mountain
Views In Private Community.
Sleeps: 6
Bedrooms: 4
Bathrooms: 3
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Private Large Lakefront
Home On Robin Hood Lake.
Sleeps: 10
Bedrooms: 6
Bathrooms: 3
Pets Welcome
Becket, MA (Sherwood Forest)
Central Berkshire Area
Berkshire Vacation Rentals
Quiet Comfortable Cabin 5 Minute
Walk To Swimming And Boating.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Two Peaceful Spaces & Outdoor Sauna,
Come Relax & Enjoy Nature!
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Luxurious, Elegant 4 Acre
Berkshire/Pioneer Valley Retreat Pool.
Sleeps: 10
Bedrooms: 5
Bathrooms: 4
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Home In The Berkshires, Has Everything
You Need For A Perfect Stay.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Serene, Private Waterfront House,
Perfect Summer Retreat!
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Home on 11 Acres
With Pond & 2 Fire Pits!
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
2BR House In The Heart Of The Berkshires, Spacious Closed Porch,
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming House With Large Porch
Near Jacob’s Pillow
Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Becket, MA (Sherwood Forest)
Central Berkshire Area
Berkshire Vacation Rentals
Peace And Quiet On The Lake
In Sherwood Forest.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
A-Frame In Sherwood Forest, Walk To A Peaceful Lake.
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
Pets Considered
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lakefront 2 Bedroom Cottage In The
Berkshires In Western Massachusetts.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Becket Contemporary Cottage In The
Woods, Private Spring Fed Pond.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
3 Bedroom Berkshire House Rental
Perfect For Families Or Groups.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
Pets Welcome
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Recently Renovated 4 BR, 2 BA Mid
Century Home On Long Bow Lake.
Sleeps: 6
Bedrooms: 4
Bathrooms: 1
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful 4 Season Lakeside Log
Home Close To Berkshires Attractions.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Private Lakefront Beach Property On
Goose Pond Near Tanglewood.
Sleeps: 5
Bedrooms: 1
Bathrooms: 1
No Pets
Becket, MA
Central Berkshire Area
Berkshire Vacation Rentals
Sprawling Ranch Nestled In Private
Wooded Lot With Expansive Yards!
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Cheshire, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Large, 19th Century Fully Renovated
Historic Barn In The Berkshires.
Sleeps: 10
Bedrooms: 3
Bathrooms: 1
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Serene Great Barrington Cottage
With Fire Pit! Nearby Hiking Trails.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Comfortable, Newly Renovated 2BR
Apartment In Historic Grist Mill.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Luxury Near Great Barrington, Location Is Ideal, Outdoor Terrace.
Sleeps: 12
Bedrooms: 4
Bathrooms: 3.5
No Pets
North Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Robin’s Retreat by AvantStay, Carriage House At Historic Inn: Barn, Pub, Farm!
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Timberdoodle, Peaceful And Tranquil
Mountainside Tree House.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Less Than 1/2 Hour From Tanglewood
& Close To The Appalachian Trail.
Sleeps: 6
Bedrooms: 4
Bathrooms: 1.5
Pets Welcome
North Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Freeman – Newly Renovated
14K SF Estate On 40 Acres.
Sleeps: 25
Bedrooms: 5
Bathrooms: 4.5
Pets Welcome
Egremont, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Amazing Ski Lodge – Incredible 7,500
Sq. Ft. Log Cabin, Sleeps 20.
Sleeps: 20
Bedrooms: 5
Bathrooms: 6.5
No Pets