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Holiday Houses in Berkshires

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787 Holiday homes

A Stunning Upstate New York Property.

Westerlo house

4 bedrooms / 3 bathrooms / sleeps 8

from £893 / night

£6,248 / week

Great Vacation House in the Berkshires by Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

4

from £173 / night

£1,206 / week

A Great Vacation Spot All Year Long

East Dorset house

3 bedrooms / 2 bathrooms / sleeps 8

from £210 / night

£1,677 - £2,329 / week

Lake House

Lakeville house

5 bedrooms / 3 bathrooms / sleeps 9

1

from £565 / night

£2,353 / week

Hudson River Villa w/Pool, Spa & Private Beach!

Athens villa

5 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 5 minutes

from £989 / night

£6,918 / week

Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

Stanfordville log cabin

1 bedroom / 1 bathroom / sleeps 2

1

from £212 / night

£1,318 / week

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 5 minutes

from £104 / night

£728 / week

The Dacha: Summer/Skiing House in the Berkshires

Treadwell apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £189 / night

£848 - £1,045 / week

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £100 / night

£637 / week

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

Responds fast! avg. 3 hours 4 minutes

from £259 / night

£1,130 / week

Harley's Hideaway, A Relaxing Escape

Stanfordville apartment

1 bedroom / 1 bathroom / sleeps 2

from £132 / night

£757 / week

Lakefront house with smaller cabin available

Lake Luzerne house

3 bedrooms / 1 bathroom / sleeps 5

2

from £179 / night

£1,252 / week

Spacious Wilmington Home w/ Game Room & Deck!

Wilmington house

6 bedrooms / 5 bathrooms / sleeps 26

Responds fast! avg. 5 minutes

from £195 / night

£1,363 / week

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 50 minutes

from £170 / night

£1,186 / week

Updated Jiminy Peak Condo w/ Patio & Pool Access!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

from £174 / night

£1,217 / week

Pristine Norwich Inn & Spa Villa Near Casinos

Norwich apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 5 minutes

from £165 / night

£1,155 / week

Peaceful setting

Dorset house

3 bedrooms / 3 bathrooms / sleeps 5

1

from £245 / night

£1,676 / week

Bromley Farm Ski House

Peru house

6 bedrooms / 5 bathrooms / sleeps 14

from £518 / night

£2,542 / week

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

from £137 / night

£800 - £866 / week

Waterfront New England House on Wickaboag Lake!

West Brookfield house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 20 minutes

from £189 / night

£1,321 / week

Newly Remodeled Townhome

Jamaica townhouse

3 bedrooms / 2 bathrooms / sleeps 12

from £471 / night

£2,824 / week

Dorset in-village summer rental

Dorset house

5 bedrooms / 4 bathrooms / sleeps 10

from £236 / night

£1,647 / week

Beauty in the Berkshires

Austerlitz house

6 bedrooms / 5 bathrooms / sleeps 14

from £1,113 / night

£6,027 / week

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

from £184 / night

£1,271 / week

#585: 12 Lilla Lane 585-02

Wilmington house

3 bedrooms / 2 bathrooms / sleeps 12

from £356 / night

£1,991 / week

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,365 / week

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

1

from £202 / night

£1,412 / week

PARADISE on EARTH! - Historic 4BR Farmhouse

West Halifax house

4 bedrooms / 2 bathrooms / sleeps 8

1

from £268 / night

£1,551 / week

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

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

from £181 / night

£1,262 / week

9 BR Lakefront Luxury Getaway on 10 Acres. Sleeps 24!

Peru house

9 bedrooms / 6 bathrooms / sleeps 24

from £706 / night

£4,941 / week

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms / 2 bathrooms / sleeps 13

1

from £395 / night

£1,532 / week

Castle Manor by the Lake: Guest Suite Sleeps 6

Saratoga Springs guest house

3 bedrooms / 3 bathrooms / sleeps 6

from £319 / night

£2,233 / week

Bright and Airy 2BR near the center

Hudson apartment

2 bedrooms / 1 bathroom / sleeps 6

from £123 / night

£855 / week

Beautiful Cottage at the foot of the Berkshires

Copake Falls cottage

2 bedrooms / 1 bathroom / sleeps 4

from £160 / night

£1,092 / week

The Perfect Vermont Experience for All Seasons

Dorset house

4 bedrooms / 3 bathrooms / sleeps 8

1

from £236 / night

£1,648 / week

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms / 4 bathrooms / sleeps 12

from £565 / night

£2,354 - £2,749 / week

The Owls Nest Cabin

West Coxsackie log cabin

1 bedroom / 1 bathroom / sleeps 2

from £184 / night

£942 / week

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 5 minutes

from £170 / night

£1,185 / week

#C230: 129 East Brook Crossing C230-03

Wilmington villa

3 bedrooms / 2 bathrooms / sleeps 7

from £329 / night

£1,838 / week

#274: 28 Old Witness Tree Lane 274-01

Wilmington villa

3 bedrooms / 2 bathrooms / sleeps 6

from £383 / night

£2,144 / week

Viewing 40 of 787
rentals in Berkshires