Holiday Houses in Berkshires

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168 Holiday homes

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 10 minutes

from £166 / night

£1,157 / week

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

from £230 / night

£1,334 / week

Updated Jiminy Peak Condo w/ Patio & Pool Access!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 10 minutes

from £171 / night

£1,192 / week

3BR Lee House w/ Easy Access to Main Street!

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 10 minutes

from £221 / night

£1,546 / week

Great Vacation House in the Berkshires by Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

4

from £171 / night

£1,196 / week

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

from £253 / night

£1,104 / week

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £101 / night

£643 / week

Unique People & Pet-Welcoming Country Haven

Charlemont apartment

1 bedroom / 1 bathroom / sleeps 4

180

from £129 / night

£768 - £1,215 / week

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

from £207 / night

£1,446 / week

2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

3

from £207 / night

£1,012 / week

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

1

from £197 / night

£1,377 / week

Rustic Berkshires Cottage, Steps to Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 10 minutes

from £102 / night

£709 / week

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

from £413 / night

£2,570 / week

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

from £276 / night

£2,024 / week

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

1

from £97 / night

£661 / week

Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / sleeps 12

2

Responds fast! avg. 2 hours 45 minutes

from £597 / night

£3,212 / week

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

from £134 / night

£782 - £847 / week

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

4

from £299 / night

£2,088 / week

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

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

7

from £322 / night

£2,249 / week

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

2

from £345 / night

£2,415 - £2,898 / week

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

8

Responds fast! avg. 2 hours 39 minutes

from £184 / night

£1,104 / week

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

7

Responds fast! avg. 1 hour 41 minutes

from £179 / night

£1,253 / week

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

from £179 / night

£1,239 / week

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

2

from £161 / night

£552 - £2,806 / week

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

13

from £137 / night

£913 / week

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

4

from £173 / night

£874 - £2,070 / week

Country Victorian Serenity in the Berkshires

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

from £210 / night

£1,469 / week

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

24

from £183 / night

£1,192 - £1,605 / week

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

from £211 / night

£1,478 / week

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

33

from £184 / night

£1,102 / week

Stunning Home! 120 Acres! Amazing!

Great Barrington house

9 bedrooms / 8 bathrooms / sleeps 16

from £3,312 / night

£23,179 / week

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

3

Responds fast! avg. 3 hours 52 minutes

from £92 / night

£780 / week

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 48 minutes

from £368 / night

£2,576 / week

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

from £551 / night

£3,855 - £5,139 / week

House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

from £874 / night

£5,473 - £5,988 / week

RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

15

Responds fast! avg. 12 minutes

from £174 / night

£1,150 / week

'Butterfly Hill' West Stockbridge Home on 3 Acres!

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 10 minutes

from £152 / night

£1,060 / week

RIVERSONG "PENTHOUSE"

North Egremont private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 12 minutes

from £138 / night

£966 / week

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

from £393 / night

£2,751 / week

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / sleeps 5

17

Responds fast! avg. 23 minutes

from £143 / night

£1,012 - £1,495 / week

Viewing 40 of 168
rentals in Berkshires

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