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

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134 Holiday homes

Holiday home in Berkshires

Williamstown house

4 bedrooms / 2 bathrooms / sleeps 6

from £123 / night

£857 / week

Berkshires holiday condo rental

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,365 / week

Holiday home in Berkshires

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

4

from £175 / night

£1,222 / week

New Marlborough holiday cottage rental

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 4 minutes

from £107 / night

£744 / week

Holiday home in Berkshires

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

from £185 / night

£1,292 / week

Holiday home in Stockbridge

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

1

from £202 / night

£1,412 / week

Berkshires holiday cottage rental

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 4 minutes

from £174 / night

£1,214 / week

Ski apartment to rent in Berkshires

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

2

from £164 / night

£563 - £1,350 / week

Holiday home with golf nearby in Hancock

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

3

from £212 / night

£1,036 / week

Holiday cottage in North Adams

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

1

from £99 / night

£676 / week

Home rental in Berkshires

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

Responds fast! avg. 3 hours 4 minutes

from £259 / night

£1,130 / week

Holiday home in Hinsdale

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

from £137 / night

£800 - £866 / week

Berkshires holiday home rental

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

from £282 / night

£2,067 / week

Farmhouse rental in Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

4

Responds fast! avg. 1 hour 34 minutes

from £306 / night

£2,141 / week

Apartment letting in Berkshires with swimming pool

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

from £178 / night

£1,246 / week

Holiday home in Monterey

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

from £423 / night

£2,960 / week

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

13

Responds fast! avg. 1 hour 1 minutes

from £141 / night

£937 / week

Holiday condo in Hancock

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

from £212 / night

£1,483 / week

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!

180

from £131 / night

£779 - £1,170 / week

Holiday home in Berkshires

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

from £184 / night

£1,271 / week

Home letting in Berkshires

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

8

Responds fast! avg. 3 hours 0 minutes

from £182 / night

£1,398 - £1,790 / week

Berkshires holiday home rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

from £402 / night

£2,815 / week

Cottage accommodation in Berkshires

Lanesboro cottage

2 bedrooms / 1 bathroom / sleeps 5

“Better than the pictures!” The schoolhouse was so charming, very get away from it all. If you plan to hike Greylock - this is the place to stay! The base parking lot is about 5 minutes away. The schoolhouse is actually on a very quiet road. Cheryl was great at organizing the stay and making sure we were taken care of. The schoolhouse has plenty of romantic qualities but was also very family friendly. The perfect combination for our first get away with our baby. The only drawback is the distance from the other towns. However, Old Forge had the best food I have had in a while and it is only 5 minutes away.

17

from £146 / night

£1,036 - £1,530 / week

Berkshires holiday home rental

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

from £894 / night

£5,600 - £6,127 / week

Apartment rental in West Stockbridge

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

3

from £95 / night

£800 / week

Holiday home rental

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

2

from £353 / night

£2,471 - £2,965 / week

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!

33

from £189 / night

£1,130 / week

Holiday home rental

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

4

from £176 / night

£886 - £2,097 / week

Holiday home in New Marlborough

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

from £213 / night

£1,491 / week

Berkshires holiday home rental

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

from £424 / night

£2,636 / week

Holiday home with golf nearby in Berkshires

Lee house

5 bedrooms / 6 bathrooms / sleeps 9

5

from £673 / night

£4,706 / week

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!

24

from £212 / night

£1,313 / week

Holiday apartment in Berkshires

Lee apartment

3 bedrooms / 2 bathrooms / sleeps 8

2

from £282 / night

£1,692 - £2,349 / week

Holiday home in Lenox

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

from £188 / night

£1,311 / week

West Stockbridge holiday home rental

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

7

Responds fast! avg. 2 hours 17 minutes

from £330 / night

£2,306 / week

Holiday home in Berkshires

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

1

from £94 / night

£588 - £1,273 / week

Cottage letting in Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

2

from £137 / night

£942 / week

Holiday home in Berkshires

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

from £564 / night

£3,946 - £5,262 / week

Tyringham holiday cottage rental

Tyringham cottage

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 1 hour 1 minutes

from £210 / night

£1,468 / week

Holiday home rental

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

from £283 / night

£1,977 - £2,636 / week

Viewing 40 of 134
rentals in Berkshires

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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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