Berkshire Vacation Rentals Page 1

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

10 Minutes To Tanglewood Via Backroads!

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!

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Vacation Rentals In Adams MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

Vacation Rentals In Alford MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

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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

Vacation Rentals In Alford MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

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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

Vacation Rentals In Alford MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

Vacation Rentals In Becket MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

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Becket, MA

Central Berkshire Area
Berkshire Vacation Rentals

Serene, Private Waterfront House,
Perfect Summer Retreat!

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

Vacation Rentals In Becket MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

Vacation Rentals In Becket MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

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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

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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

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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

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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

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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

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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

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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

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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

Vacation Rentals In Egremont MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

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

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