Viewing 40 of 835 rentals in Berkshires
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Houses in Berkshires and Condos – Holiday Lettings - Holiday Rentals Berkshires
752 Holiday homes
from £139 / night
£727 - £1,859 / week
from £693 / night
£4,156 / week
“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 £138 / night
£919 / week
“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 £185 / night
£1,109 / week
from £273 / night
£1,386 / week
from £139 / night
£970 / week
from £324 / night
£2,263 / week
from £157 / night
£1,099 / week
from £139 / night
£832 / week
from £139 / night
£832 / week
from £139 / night
£878 / week
from £185 / night
£1,109 / week
from £93 / night
£646 / week
from £693 / night
£2,771 / week
from £550 / night
£3,048 / week
from £98 / night
£684 - £1,718 / week
from £660 / night
£4,618 / week
“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 £221 / night
£1,477 / week
from £277 / night
£1,940 / week
from £264 / night
£1,848 / week
from £208 / night
£1,455 / week
from £370 / night
£2,586 / week
from £254 / night
£1,109 / week
from £212 / night
£1,478 / week
from £176 / night
£942 - £1,007 / week
“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 £241 / night
£1,432 - £2,887 / week
from £301 / night
£2,102 - £2,748 / week
from £554 / night
£3,873 / week
from £210 / night
£1,201 / week
from £2,309 / night
£27,669 / week
from £347 / night
£2,425 / week
from £647 / night
£2,263 - £3,815 / week
from £600 / night
£4,196 / week
from £531 / night
£3,718 / week
from £462 / night
£3,233 / week
from £277 / night
£1,933 / week
from £102 / night
£647 / week
from £641 / night
£3,689 / week
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.
Top Destination reviews
Also consider
- North America Holidays 851871 properties
- United States Holidays 811575 properties
- Lenox 66 properties
- Lee 60 properties
- Stockbridge 53 properties
- Pittsfield 47 properties
- Williamstown 30 properties
- Becket 27 properties
- Otis 24 properties
- North Adams 23 properties
- New Marlborough 21 properties
- Lanesborough 18 properties
- North Egremont 17 properties
- Hinsdale 13 properties
- Richmond 12 properties
- Sandisfield 10 properties
- South Lee 8 properties