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Sheffield Rentals

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Price range

Per night

$10 - $500

Sheffield Rentals

126 Houses

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$515

1 / 13

Apple Cottage

Sheffield farmhouse

3 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 3 hours 22 minutes

Price per night from

$430

1 / 10

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$573

1 / 14

Great rentals within 20 miles that match your search

chestnut lodge Queens Room

Lee b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 36 minutes

Price per night from

$165

1 / 2

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,369

1 / 29

the BIG room at chestnut lodge

Lee b and b

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 36 minutes

Price per night from

$228

1 / 7

4 Bedroom Furnished House in Lakeville Connecticut

Lakeville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$371

1 / 42

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b

Price per night from

$343

1 / 30

RIVERSONG "PENTHOUSE"

North Egremont room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 23 minutes

Price per night from

$172

1 / 32

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$143

1 / 6

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits

Price per night from

$376

1 / 18

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 29 minutes

Price per night from

$115

1 / 8

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 13

Price per night from

$248

1 / 12

Spacious Berkshires Home w/ Pool & Patio!

North Egremont house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 10 minutes

Price per night from

$858

1 / 36

1 Bedroom Hudson Valley Farm House

Craryville guest house

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$366

1 / 18

Country Victorian Serenity in the Berkshires

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$262

1 / 10

Cottage on East Twin Lakes, Internet Access, A/C.

Salisbury cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$180

1 / 12

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 37 minutes

Price per night from

$172

1 / 14

The Barn at Copake Lake

Craryville barn

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$685

1 / 10

Mountain Views Atop Blueberry Hill on 40 Acres

Austerlitz house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$229

1 / 18

Overnight at Althouse -Higgins

Hillsdale apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$200

1 / 11

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$223

1 / 18

3BD Newly Rennovated Contempoary Near Stockbridge

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$343

1 / 26

Escape to Avalon Cottage in the Hudson Valley

Craryville house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$166

1 / 16

Rustic Rivers end room in the barn at chestnut lodge

Lee barn

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 36 minutes

Price per night from

$178

1 / 6

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$258

1 / 30

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 26 minutes

Price per night from

$229

1 / 14

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$206

1 / 37

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$489

1 / 24

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are

Price per night from

$171

1 / 13

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 43 minutes

Price per night from

$258

1 / 10

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

Tyringham house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 43 minutes

Price per night from

$287

1 / 9

Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

Stockbridge cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 12 minutes

Price per night from

$343

1 / 24

Evergreen Pines Country Estate Villa

Ancram house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,289

1 / 30

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$216

1 / 18

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe

Price per night from

$487

1 / 18

S. Berkshires Mountain Treehouse • Views • Privacy

Great Barrington house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$213

1 / 15
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