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Enjoy horses and the largest recreational lake in Massachusetts
East Otis apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
Price per night from
$126
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Hinsdale house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$218
Responds fast! avg. 3 hours 37 minutes
Price per night from
$258
Price per night from
$573
“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))
Price per night from
$171
Berkshires: Romantic Cottage with spectacular view
Great Barrington cottage
- 1 bedroom
- 1 bathroom
- sleeps 3
“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!
Responds fast! avg. 1 hour 16 minutes
Price per night from
$274
“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.
Price per night from
$229
Price per night from
$172
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
Price per night from
$373
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.
Price per night from
$298
Price per night from
$859
One of the Finest Homes and Best location in the Berkshires
Stockbridge house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Price per night from
$802
Price per night from
$263
Price per night from
$172
Responds fast! avg. 1 hour 38 minutes
Price per night from
$859
Price per night from
$2,863
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
Hancock studio
- Studio
- 1 bathroom
- sleeps 4
Price per night from
$122
Private Home Overlooking Stevens Lake (31 Night Min)
Great Barrington house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$572
Responds fast! avg. 1 hour 56 minutes
Price per night from
$156
Price per night from
$629
Price per night from
$327
Price per night from
$532
Price per night from
$172
Price per night from
$682
Price per night from
$195
Price per night from
$457
6BR Berkshire Bliss - 38 private acres - close to skiing and town
Lanesborough house
- 6 bedrooms
- 5 bathrooms
- sleeps 15
Price per night from
$795
Viewing 38 of 57
rentals in Berkshires
About Berkshires
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 vacation rental, such as a secluded cabin in the woods. Wake up in your vacation 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 caliber, emerald green golf courses throughout the Berkshires region.
No matter what activities you have in mind for your vacation 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 vacation rental. Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great vacation 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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