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Holiday Houses in Berkshires

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98 Holiday homes

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Monterey cottage

1 bedroom / 1 bathroom / sleeps 4

1

Responds fast! avg. 2 hours 4 minutes

from £98 / night

£686 / week

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £95 / night

£602 / week

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

from £237 / night

£1,031 / week

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

from £164 / night

£880 - £1,036 / week

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 32 minutes

from £219 / night

£1,271 / week

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 2 hours 4 minutes

from £160 / night

£1,119 / week

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

35

from £178 / night

£1,066 / week

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

1

from £99 / night

£676 / week

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

from £439 / night

£3,073 / week

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

2

from £154 / night

£525 - £1,260 / week

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

13

from £130 / night

£866 / week

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

24

from £207 / night

£1,282 / week

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

4

from £162 / night

£819 / week

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 42 minutes

from £197 / night

£1,378 / week

Unique People & Pet-Welcoming Country Haven

Charlemont apartment

1 bedroom / 1 bathroom / sleeps 4

180

from £130 / night

£822 - £1,185 / week

Traditional Lenox Home, Walk to Downtown & Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

from £163 / night

£1,142 / week

Lake House

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

5

from £673 / night

£4,706 / week

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

from £405 / night

£2,832 / week

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

from £163 / night

£966 - £2,319 / week

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

3

from £91 / night

£768 / week

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

9

from £172 / night

£1,031 / week

"Fall" in love with the Berkshire or "Winter in !!!

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

7

from £308 / night

£2,152 / week

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

1

from £86 / night

£541 - £1,173 / week

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

4

Responds fast! avg. 3 hours 16 minutes

from £258 / night

£2,276 - £2,997 / week

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

from £168 / night

£1,177 / week

House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

from £894 / night

£5,600 - £6,127 / week

3BD Newly Rennovated Contempoary Near Stockbridge

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

from £283 / night

£1,977 - £2,636 / week

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

from £564 / night

£3,946 - £5,262 / week

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

42

from £224 / night

£1,331 - £2,684 / week

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

from £337 / night

£2,246 / week

Heart of Lenox

Lenox house

2 bedrooms / 2 bathrooms / sleeps 4

2

Responds fast! avg. 3 hours 28 minutes

from £128 / night

£895 / week

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms / 2 bathrooms / sleeps 8

2

from £263 / night

£1,577 - £2,190 / week

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 23 minutes

from £604 / night

£2,112 - £3,560 / week

Family-friendly Cottage Near Lake, Tanglewood

Stockbridge cottage

3 bedrooms / 2 bathrooms / sleeps 7

6

from £245 / night

£1,718 / week

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

from £664 / night

£3,985 / week

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

2

Responds fast! avg. 1 hour 33 minutes

from £200 / night

£1,395 / week

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

from £141 / night

£844 / week

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

from £216 / night

£1,506 / week

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Otis log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 4 minutes

from £72 / night

£499 / week

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 7 minutes

from £661 / night

£2,644 / week

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rentals in Berkshires