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Houses in Berkshires and Cottages – Holiday Lettings - Holiday Rentals Berkshires

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86 Holiday homes

Monterey holiday cottage rental

Monterey cottage

1 bedroom • 1 bathroom • sleeps 4

from £95 / night

£664 / week

1 / 25

Berkshires holiday cottage rental

Monterey cottage

2 bedrooms • 1 bathroom • sleeps 2

from £155 / night

£1,084 / week

1 / 24

Home rental in Berkshires

Becket house

4 bedrooms • 3 bathrooms • sleeps 8

from £229 / night

£999 / week

1 / 20

Holiday home in Hinsdale

Hinsdale house

3 bedrooms • 2 bathrooms • sleeps 6

from £158 / night

£849 - £998 / week

1 / 10

Holiday home in Monterey

Monterey house

4 bedrooms • 5 bathrooms • sleeps 10

from £375 / night

£2,620 / week

1 / 23

Holiday home in Becket

Becket house

2 bedrooms • 1 bathroom • sleeps 4

“serenity” I walked in and knew this is exactly what I hoped for. The coziness ,made me feel like i was home. The deck with a babbling brook running under you was so peacefull.There was'nt anything you would need, whether in or out with a nice shed for outdoor activities..I'm definetely going back to canoe on the lake.It was a little too chilly during my 4 day stay. I'd reccommend this cottage to anyone that likes to get away from the fast life everyone seems to lead

from £124 / night

£829 / week

1 / 13

Holiday condo in Hancock

Hancock condo

1 bedroom • 2 bathrooms • sleeps 4

from £188 / night

£1,312 / week

1 / 14

Holiday apartment in Charlemont

Charlemont apartment

1 bedroom • 1 bathroom • sleeps 4

“Weekend Getaway” After a full and tiring day of location scouting in the frigid climate of the Berkshires, this rental was just the thing we needed. A home away from home, we took no time at all cozying up inside. And being able to find a place to bring our dog is usually a nuisance at the very least, so not having to board the lil guy was an unexpected bonus. Pat was wonderful and very hospitable. We awoke the next morning to find a basket of freshly baked scones and fresh orange juice. This place was a perfect find and we will certainly be back again. Thanks Pat!

from £125 / night

£790 - £1,140 / week

1 / 37

Berkshires holiday home rental

Monterey house

5 bedrooms • 2 bathrooms • sleeps 6

from £463 / night

£3,236 / week

1 / 29

Holiday apartment in Berkshires

Lenox apartment

4 bedrooms • 1 bathroom • sleeps 7

“We love our visits to Gartner House, a hidden treasure!” I've stayed at Gartner House a few times over the past 3 years, the last time in Dec 2011. Deb artfully furnishes each room with antiques in a different color theme - especially love the rose and the lavender bedrooms. It's extremely clean, comfortable, roomy, with a home-like atmosphere within a block of downtown Lenox - you won't be disappointed. We've gone as a couple or with a group - there are 4 bedrooms so plenty of room. This place is a hidden gem!

from £167 / night

£1,001 / week

1 / 21

Holiday home rental

Great Barrington house

4 bedrooms • 2 bathrooms • sleeps 10

from £182 / night

£914 / week

1 / 18

Holiday home with golf nearby in Berkshires

Lee house

5 bedrooms • 6 bathrooms • sleeps 9

from £594 / night

£4,155 / week

1 / 18

Holiday cottage letting

Great Barrington cottage

1 bedroom • 1 bathroom • sleeps 3

“A Breath of Spring” An enchanting cottage nestled into the quiet and calm of the Berkshire Hills. Birdsong and a cocoon of green calm the senses and stir the heart. An excellent location and very kind and thoughtful hosts. Minutes away from excellent restaurants, beautiful walks and interesting cultural venues. As a painter, I painted the entire time, couldn't stop myself from absorbing all that beauty onto canvas. The pool is an added bonus as a sheltered quiet place to sun bathe and swim. The cottage is simple but complete. No stove but a microwave and fridge to prepare easy meals. A very relaxing, nurturing and romantic getaway!

from £199 / night

£1,243 - £1,579 / week

1 / 18

Holiday apartment in Berkshires

Lee apartment

3 bedrooms • 2 bathrooms • sleeps 8

from £270 / night

£1,888 - £2,468 / week

1 / 12

Holiday home in Lenox

Lenox house

3 bedrooms • 3 bathrooms • sleeps 6

from £158 / night

£1,106 / week

1 / 24

Holiday home in Berkshires

Hancock house

4 bedrooms • 2 bathrooms • sleeps 8

from £104 / night

£655 - £1,674 / week

1 / 26

Holiday home in Berkshires

Otis house

6 bedrooms • 5 bathrooms • sleeps 14

from £499 / night

£3,490 - £4,654 / week

1 / 22

Berkshires holiday home rental

Savoy house

2 bedrooms • 1 bathroom • sleeps 4

from £167 / night

£999 / week

1 / 6

Holiday home in Berkshires

Great Barrington house

5 bedrooms • 4 bathrooms • sleeps 12

from £250 / night

£2,206 - £2,906 / week

1 / 30

Berkshires holiday home rental

Monterey house

• 2 bathrooms • sleeps 7

from £149 / night

£1,039 / week

1 / 12

Apartment rental in Lee with shared pool

Lee apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £312 / night

£2,078 / week

1 / 12

Holiday home in Lenox

Lenox house

2 bedrooms • 2 bathrooms • sleeps 4

from £209 / night

£1,458 / week

1 / 12

Holiday home rental

West Stockbridge house

5 bedrooms • 2 bathrooms • sleeps 15

“Charming Berkshire Farmhouse” We're a group of five high school friends who get together yearly for a long weekend reunion. Elaine's house was just perfect for us--comfortable, roomy and well equipped not to mention charming! For an older home, it is extremely well maintained. The screened in porch was our favorite place to gather. The location was great with easy access to the many adventures that the area has to offer. Elaine was wonderful to work with and a good host once we arrived. We highly recommend.

from £217 / night

£1,291 - £2,602 / week

1 / 20

Stockbridge holiday home rental

Stockbridge house

4 bedrooms • 3 bathrooms • sleeps 10

from £583 / night

£2,040 - £3,438 / week

1 / 19

Holiday home in Berkshires

Stockbridge house

3 bedrooms • 2 bathrooms • sleeps 6

from £624 / night

£3,740 / week

1 / 22

Holiday home rental

Stockbridge house

3 bedrooms • 2 bathrooms • sleeps 6

from £193 / night

£1,351 / week

1 / 30

Cottage accommodation in Berkshires

Stockbridge cottage

3 bedrooms • 2 bathrooms • sleeps 7

from £238 / night

£1,665 / week

1 / 16

Berkshires holiday condo rental

Williamstown condo

2 bedrooms • 1 bathroom • sleeps 4

from £191 / night

£1,332 / week

1 / 6

Holiday farmhouse in Berkshires

Stockbridge farmhouse

1 bedroom • 1 bathroom • sleeps 3

from £125 / night

£750 / week

1 / 4

Holiday home in Berkshires

Lee house

5 bedrooms • 5 bathrooms • sleeps 12

from £626 / night

£2,502 / week

1 / 7

Holiday log cabin rental

East Otis log cabin

2 bedrooms • 1 bathroom • sleeps 4

from £69 / night

£484 / week

1 / 24

Berkshires ski home to rent.

Becket house

3 bedrooms • 3 bathrooms • sleeps 8

from £280 / night

£1,958 / week

1 / 42

Great Barrington holiday home rental

Great Barrington house

3 bedrooms • 2 bathrooms • sleeps 4

from £125 / night

£790 / week

1 / 14

Holiday home in Berkshires

Hancock house

2 bedrooms • 2 bathrooms • sleeps 4

from £2,078 / night

£24,894 / week

1 / 4

Holiday farmhouse in Berkshires

Stockbridge farmhouse

1 bedroom • 1 bathroom • sleeps 2

from £125 / night

£750 / week

1 / 4

Holiday home in Lenox

Lenox house

3 bedrooms • 2 bathrooms • sleeps 6

from £159 / night

£1,113 / week

1 / 24

Holiday studio in Berkshires

Hancock studio

Studio • 1 bathroom • sleeps 4

from £77 / night

£533 - £2,440 / week

1 / 67

Holiday home in Berkshires

Lenox house

2 bedrooms • 2 bathrooms • sleeps 4

from £291 / night

£2,032 / week

1 / 25

Berkshires holiday tented camp accommodation

Southfield tented camp

1 bedroom • 1 bathroom • sleeps 8

from £125 / night

£991 - £1,189 / week

1 / 12

Holiday home in Berkshires

Stockbridge house

4 bedrooms • 4 bathrooms • sleeps 12

from £415 / night

£2,905 / week

1 / 31

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Berkshires holidays

A Berkshires getaway in the Berkshire Mountains of Massachusetts is the perfect way to escape the bustle of everyday life and experience breathtaking natural beauty. Get the most out of your time here by staying in a holiday rental, such as a secluded cabin in the woods. Wake up in your holiday rental to the sound of birds and forest life, and enjoy coffee on your private balcony as the sun rises. Then wander downtown to explore the shops, local museums, and unique independent art galleries. In the afternoon, head for the trails to hike to cascading waterfalls, experience a Berkshires zip line adventure, or take an ATV tour. At the end of a busy day, retreat to your home away from home and host a barbeque or a game night for your family and friends.

Here are a few additional suggestions for your trip:

  • Go horseback riding: There are several well-maintained stables in the Berkshires area that offer lessons or guided single and multi-day trail rides.
  • Take a snowmobiling lesson: During the winter, the back country trails through the mountains are perfect for snowmobiling. Take a lesson or join a group adventure.
  • Go skiing or snowshoeing: Cross country skis offer a quieter way to explore the pristine snowy trails and increase opportunities to spot elusive wildlife like foxes and black bears.
  • Go fishing: Take a fly fishing trip along the winding, hidden waterways, or rent a boat and cast your line in the lake at sunrise.
  • Spend an afternoon in the spa: Indulge in a day of pampering at a Berkshires spa with a manicure, pedicure, or hot rock massage.
  • Play golf: Tee off at any one of several champion calibre, emerald green golf courses throughout the Berkshires region.

No matter what activities you have in mind for your holiday or what time of year you plan to visit the Berkshires, you'll find endless things to do here, and the best way to enjoy it all is with your own private holiday rental. Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great holiday memories. While you're in the Berkshires, you may also want to visit the coast and explore the historic villages of Cape Cod.

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