Seasonal Rentals In The Berkshires and Columbia County New York
APRIL HILL
Richmond, MA
Grand and Stately Colonial, Meticulously Restored, Spectacular Views and Privacy, Manicured Grounds, Guest House, Pool and Barn.
Exclusively offered at $30,000
The Winthrop Estate
Lenox, MA
A magnificent thirty acre estate from the gilded age with modern amenities and central air-conditioning in Lenox, Massachusetts
Set on more than thirty acres in the...
Exclusively offered at $28,000
BLUEBERRY HILL
West Stockbridge, MA
A Private Compound
with glorious mountain views, tennis and a private swimming pool.
Exclusively offered at $22,000
BLUE HILL ROAD
Great Barrington, MA
A spectacular Contemporary with central air, year-round swimming pool and unparalleled views.
Exclusively offered at $20,000
SOUTH HOUSE
Tyringham, MA
a spectacular family compound on 111 acres privately located in Tyringham.
Exclusively offered at $20,000
STOCKBRIDGE BOWL COLONIAL
Stockbridge, MA
A 5 bedroom colonial with some air conditioning
and a private beach on Stockbridge Bowl.
Exclusively offered at $18,000
APPLE HILL
West Stockbridge, MA
Remarkable Compound with distant mountain views, swimming pond and privacy.
Exclusively offered at $18,000
INGLESIDE
Stockbridge, MA
Walk to Town and Golf Course, Gorgeous 17+ Acres, Pool and Pool House, Gracious Home with 9 Fireplaces
Exclusively offered at $18,000
STOCKBRIDGE BOWL COLONIAL
Stockbridge, MA
A 5 bedroom colonial with some air conditioning
and a private beach on Stockbridge Bowl.
Exclusively offered at $18,000
THE CARRIAGE HOUSE
Stockbridge, MA
A recently renovated 3 bedroom Carriage House with central air conditioning.
Exclusively offered at $15,000
CASTLE HILL
Stockbridge, MA
Dazzling views with 4 air-conditioned bedrooms
Exclusively offered at $15,000
EAST DUGWAY ROAD
Lenox, MA
A pristine 4 bedroom Colonial with central air.
Exclusively offered at $15,000
Kemble Street
Lenox, MA
A SPACIOUS 5 BEDROOM COLONIAL WITH A PRIVATE POOL,SOME AIR CONDITIONING AND 1st FLOOR MASTER.
Exclusively offered at $15,000
The Meadows
Lenox, MA
An exceptional rental property with 4 air-conditioned bedrooms with private tennis located within a walk to downtown Lenox.
Exclusively offered at $15,000
TOFU'S RETREAT
Alford, MA
A renovated 3 bedroom contemporary with swimming pool.
Exclusively offered at $14,000
WELCOME TO THE LAKE
Richmond, MA
A Contemporary waterfront lake cottage with 5 bedrooms and two baths!
Air-conditioned bedrooms! Bring your own boat!
Exclusively offered at $14,000
SADDLEBACK RETREAT
Pittsfield, MA
A 5 bedroom waterfront contemporary home with central air on Onota Lake. Bring your boat!
Exclusively offered at $14,000
BELLA'S HAVEN
Great Barrington, MA
This stylish contemporary farmhouse is the perfect summer get away on 2.44± acres in To Ho Ne Shores on Lake Buel. Near all cultural attractions and 5 minutes to Great...
Exclusively offered at $14,000
BEAUTIFUL CONTEMPORARY WITH VIEWS
Monterey, MA
The delightful Lake Garfield beach is less than 2 miles. Swim, boat and fish. 4 privates suites sleep 8.
Exclusively offered at $13,000
BIRCH RISE
West Stockbridge, MA
Stunning Contemporary with central air.
Exclusively offered at $12,500
FAMILY COMPOUND WITH POOL AND TENNIS COURT
Great Barrington, MA
Available for July - Summer Fun at this Family Compound with Heated Pool and Tennis Court . Minutes from the Heart of Great Barrington
Exclusively offered at $12,500
COVE LANE
Stockbridge, MA
A recently updated 3 bedroom Stockbridge Bowl waterfront cottage.
Air conditioned bedrooms. Bring your boat!
Exclusively offered at $12,000
WILLARD HILL
Stockbridge, MA
A 4 bedroom brick Federal with 3 baths and air-conditioned master.
Exclusively offered at $12,000
LEDGES
Stockbridge, MA
A 3 bedroom Stockbridge Bowl waterfront Contemporary.
Exclusively offered at $10,000
TANGLEWOOD RETREAT
Lenox, MA
A renovated air-conditioned contemporary home with 3 bedrooms and a grand piano
3 minute walk to Tanglewood
Exclusively offered at $10,000
THE ROOST
Stockbridge, MA
Two converted 19th century barns make a delightful vacation home with central air.
Exclusively offered at $10,000
BERKSHIRE SERENITY
Glendale, MA
This privately located colonial has 4 bedrooms, 3 1/2 baths, a hot tub and screened porch.
Exclusively offered at $10,000
The Maple House
Lenox, MA
Located on a quiet street, the Maple House has central air-conditioning, 3 bedrooms, and 2 full baths and is an easy walk to the village center.
Exclusively offered at $10,000
BY THE LAKE
Stockbridge, MA
This contemporary home has a spacious 2 story living room overlooking the length of the lake.
The view is breathtaking and the location is both private but close to all...
Exclusively offered at $9,000
THE LOG HOUSE
West Stockbridge, MA
A 3 bedroom lodge with a perennial stream and river frontage - Air conditioning
Exclusively offered at $8,500
GLENWOOD
West Stockbridge, MA
PRIVACY ON A QUIET ROAD, 3 BEDROOMS, 2 1/2 BATHS
Exclusively offered at $8,500
ALEXANDER McCUE HOUSE
Stockbridge, MA
A New England Home with three bedrooms, 2 full baths and central air
Exclusively offered at $8,000
EGREMONT IDYLL
Egremont, MA
A charming 4 bedroom Cottage tucked away on a quiet country road
Exclusively offered at $8,000
Osceola
Richmond, MA
Situated in Richmond, 10 minutes from downtown Pittsfield, with easy access to all Berkshires amenities. 3 bedrooms, 3 full baths.
Exclusively offered at $8,000
The Lodge
West Stockbridge, MA
The Lodge at Pixley Hill Road with air conditioning and 2 bedrooms with a sleeping loft and a digital screening room.
Exclusively offered at $8,000
COUNTRY VACATION HOME
Egremont, MA
Rustic appeal with 2 grand pianos and spectacular views
Exclusively offered at $7,000
PROCTER'S GAMBOL
Stockbridge, MA
Air-conditioned Stockbridge Bowl waterfront A-frame with with 2 bedrooms and a sleeping loft.
Exclusively offered at $7,000
Yokum Pond Retreat
Becket, MA
This beautifully appointed contemporary home with 3 bedrooms, 3 ½ baths,screened-in porch & deck. Access to 3 boating docks, 2 great ponds, tennis court, basketball...
Exclusively offered at $7,000
STOCKBRIDGE CAPE
Stockbridge, MA
A comfortable home located in a quaint New England village
(some air conditioning)
Exclusively offered at $6,500
BERKSHIRE RETREAT
Monterey, MA
A stylish 3 bedroom farmhouse with air conditioning and a hot tub in a convenient country setting Close to Ski Butternut! Air conditioned bedrooms and living room.
Exclusively offered at $6,500
179 ACRE COMPOUND IN WEST STOCKBRIDGE/AUSTERLITZ
West Stockbridge, MA
Main house $6500/mo. July and August
Cottage is $4500/mo.
Also available monthly immediately.
This unique country compound includes 2 houses and 179 beautiful...
Exclusively offered at $6,500
FIELD OF DREAMS
Lenox, MA
A centrally air conditioned home with a pool on 14 acres and just a walk to the center of Lenox
Exclusively offered at $6,000
JAKE'S FAULT FARM
Great Barrington, MA
A Contemporary Victorian Farmhouse on 30 acres with 360° views!
Exclusively offered at $6,000
SECLUDED HIDEAWAY
Stockbridge, MA
A 4 bedroom, 3 1/2 bath contemporary
Exclusively offered at $5,000
PLEASANT STREET IN SOUTH LEE
Lee, MA
GLEAMING IN-TOWN 3 BEDROOM FARMHOUSE WITH SOME A/C
Exclusively offered at $5,000
MERRYBROOK BARN
Tyringham, MA
A comfortable converted barn with a/c located in a quiet village
Exclusively offered at $4,500
Stunning In-Town Barn
Stockbridge, MA
Just A Few Years Old, Housatonic River Views, First Floor Master, Exquisite Design and Execution, Walk to Town
Exclusively offered at $4,500
CENTER OF STOCKBRIDGE VILLAGE
Stockbridge, MA
Steps from Renowned Berkshire Theater Festival, Two Block Walk to the Red Lion, One Block From Municipal Tennis
$4500 per Month
Exclusively offered at $4,500
ASHINTULLY COTTAGE
Tyringham, MA
A quaint 4 bedroom cottage surrounded by Ashintully Gardens and hiking trails
Exclusively offered at $3,500
East View
West Stockbridge, MA
Charming converted barn within walking distance of the village of West Stockbridge where you will find great shops and restaurants.15 minutes to Great Barrington. Easy...
Exclusively offered at $2,500
TREE FARM ROAD
Stockbridge, MA
A Salt Box Colonial with a bright open interior just 3 miles to Tanglewood.
Exclusively offered at $0
MAPLE STREET
Stockbridge, MA
A newly renovated 3 bedroom home in the village with central air
and a Boat Slip on Stockbridge Bowl (subject to availability)
Exclusively offered at $0
ORCHARD HOUSE
West Stockbridge, MA
STYLISH 3 BEDROOM CONTEMPORARY, ORCHARD VISTAS, WALK-TO-TOWN, PRIVACY
Exclusively offered at $0
EYEBROW COLONIAL
Stockbridge, MA
A newly renovated home with Central Air, 2 bedrooms and 2 baths
Exclusively offered at $0
Charming Sheffield Village Home
Sheffield, MA
Private and Gorgeous In Town Location., Modern and Lovely, Beautiful Screened Porch, Handsome Wood Burning Fireplace,
Exclusively offered at $0
