Holiday Houses in Berkshires

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147 Holiday homes

Great Vacation House in the Berkshires by Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

4

from £174 / night

£1,214 / week

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 16 minutes

from £106 / night

£742 / week

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £103 / night

£651 / week

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

Responds fast! avg. 2 hours 28 minutes

from £256 / night

£1,116 / week

Updated Jiminy Peak Condo w/ Patio & Pool Access!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

from £178 / night

£1,244 / week

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

from £136 / night

£794 - £859 / week

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

from £182 / night

£1,256 / week

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

from £234 / night

£1,354 / week

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

1

from £200 / night

£1,401 / week

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

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 16 minutes

from £185 / night

£1,289 / week

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 6 minutes

from £173 / night

£1,211 / week

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

33

from £186 / night

£1,116 / week

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

1

from £98 / night

£668 / week

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

from £399 / night

£2,791 / week

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

from £280 / night

£2,054 / week

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

from £419 / night

£2,604 / week

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

8

Responds fast! avg. 1 hour 25 minutes

from £182 / night

£1,395 - £1,786 / week

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

4

Responds fast! avg. 2 hours 3 minutes

from £304 / night

£2,124 / week

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

2

from £163 / night

£558 - £1,339 / week

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

13

from £139 / night

£926 / week

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

24

from £186 / night

£1,213 - £1,540 / week

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

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

3

from £210 / night

£1,023 / week

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

4

from £175 / night

£884 - £2,092 / week

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

from £210 / night

£1,471 / week

Unique People & Pet-Welcoming Country Haven

Charlemont apartment

1 bedroom / 1 bathroom / sleeps 4

180

from £131 / night

£780 - £1,172 / week

Traditional Lenox Home, Walk to Downtown & Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 16 minutes

from £178 / night

£1,242 / week

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

5

from £665 / night

£4,649 / week

RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

15

Responds fast! avg. 7 minutes

from £177 / night

£1,167 / week

Country Victorian Serenity in the Berkshires

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

from £213 / night

£1,488 / week

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

from £374 / night

£2,614 / week

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

from £173 / night

£1,027 - £2,465 / week

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

3

from £93 / night

£791 / week

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

8

from £186 / night

£1,116 / week

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

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

7

Responds fast! avg. 3 hours 17 minutes

from £327 / night

£2,287 / week

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

1

from £94 / night

£588 - £1,275 / week

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

4

from £279 / night

£2,464 - £3,245 / week

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

from £167 / night

£1,167 / week

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / sleeps 5

17

from £145 / night

£1,027 - £1,517 / week

House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

from £887 / night

£5,554 - £6,077 / week

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

2

from £350 / night

£2,451 - £2,941 / week

Viewing 40 of 147
rentals in Berkshires