Embrace the Outdoors with Berkshires Rentals!

Berkshires rentals offer the perfect opportunities for couples and adventure-seekers to enjoy great vacations. While there is something to suit all ages in the Berkshires, it is mainly a destination for those who are looking to get away from it all and enjoy nature.

Berkshires Rentals for Romantic Getaways


Couples particularly enjoy the Berkshires due to its picturesque settings and abundance of culture. Imagine sipping wine on the porch of your rental. House rentals in the Berkshires offer beautiful backdrops that help to create cozy, romantic atmospheres. In the summer months, there is nothing more romantic than sitting and watching the stars with your loved one. If you are traveling in winter, there are also some fantastic winter rentals the Berkshires has to offer.

Winter Rentals in the Berkshires Make for Unique Vacation Experiences


You will find that winter rentals in the Berkshires provide you with the ideal bases for skiing. Berkshire County is situated in Massachusetts and has some fantastic skiing locations. You can take part in cross country skiing or even snowshoeing if you prefer. There are plenty of winter activities to keep you entertained. When you aren’t skiing, why not take a trip to the nearby towns and shop until you drop? The winter house rentals in the Berkshires are not to be missed; they enable you to have a fantastic winter vacation.

Take Hikes near House Rentals in the Berkshires


One of the major attractions for tourists in the Berkshires is hiking. Fall is a particularly great time of year to experience the various hiking routes in the county. You should find that many Berkshires rentals are situated right next to the best hiking trails. If you do travel in fall, then it is recommended that you go on the Mohawk Trail. Remember to take your camera as there is plenty of beautiful scenery to be enjoyed along the way!

Typically, the Berkshires is a place to be explored. The activities tend to be slightly more cultured than you would find in many other destinations. This makes Berkshires rentals ideal for the travelers who want to experience something different on their vacations. The great thing about house rentals in the Berkshires is that you get the privacy of a home and the convenience to come and go as you please. Don’t forget that winter rentals in the Berkshires are just as great as summer rentals. There is so much to see and do no matter when you visit the county! Search now!

Learn more about things to do in the Berkshires.

Looking for Berkshires rentals? Narrow down your search by destination: Becket apartments, Great Barrington condos, Lee condos, Lenox rentals, and Stockbridge houses!

Vacation Rentals in Berkshires, Massachusetts

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Charming secluded Stockbridge home, 4 miles Tanglewood

— Property 266327
Berkshires house rental - Secluded five acre setting
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, lake, mountain, air-conditioning
Rates - per property (USD)
$350/night
$2,000/week
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Private Large Contemporary Victorian with Pool

— Property 100415
Berkshires house rental
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, mountain, rural, terrace
Rates - per property (USD)
$11,000/month
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Perfect for country site lovers RENT part of Historic House mthly or weekends

— Property 234621
Berkshires apartment rental - Deck with your entrance door
1 Bedroom, Sleeps 3,
Apartment, 1 Bathroom, rural, garden
Rates - per property (USD)
$140 - $175/night
$750 - $850/week
$750 - $1,900/month
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Log Cabin in the Northern Berkshires. Modern and Comfortable...

— Property 136759
Berkshires cabin rental - sunrise first snow
1 Bedroom, Sleeps 3,
Cabin, 1 Bathroom, mountain, rural, pets considered
Rates - per property (USD)
$110 - $150/night
$760/week
Calendar Updated Nov 19 2009

Property Review

We so much enjoyed our stay at the cabin. It was clean, comfortable, and well stocked. It was peaceful and beautiful. It was PERFECT!!!
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Getaway in the Berkshires. Great Barrington has it all. Credit cards accepted

— Property 209775
Berkshires house rental - Front of house
5 Bedrooms, Sleeps 10,
House, 2 Bathrooms, mountain, town, internet access
Rates - per property (USD)
$150 - $175/night
$1,250 - $1,800/week
$3,200 - $3,500/month
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OverBrook: Book Now For The Holidays & 2010

— Property 101135
Berkshires house rental - OverBrook
3 Bedrooms, Sleeps 12,
House, 2 Bathrooms, 1 Half Bath, lake, village, garden
Rates - per property (USD)
$175 - $250/night
$1,400 - $2,000/week
$4,000 - $7,000/month
Calendar Updated Nov 20 2009

Property Review

wow! what a great rental experience. the house was so charming AND quiet; so quiet we could hear the Canada geese fly overhead at night while we enjoyed the beautiful fireplace and a home cooked...
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Beautiful Contemporary Home by Stockbridge Bowl

— Property 223361
Berkshires house rental - Lovely Wooded Setting
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, lake, mountain, balcony
Rates - per property (USD)
$1,000 - $2,750/week
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Monterey Home - Very Private, Outdoor Hot Tub, Close to Lake, Town & Skiiing

— Property 227690
Berkshires house rental - View of living room from upstairs loft
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, lake, mountain, garden
Rates - per property (USD)
$200 - $225/night
$1,100 - $1,300/week
$3,500 - $4,500/month
Calendar Updated Nov 19 2009

Property Review

we spent a wonderful weekend here -- the house is beautifully situated, peaceful, and well-equipped. couldn't have asked for more.
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Special Prices for the Fall and Early Winter Seasons for this luxurious home.

— Property 136689
Golf
Ski
Berkshires house rental - House from the West
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, mountain, rural, garden
Rates - per property (USD)
$150 - $325/night
$750 - $2,200/week
$3,700 - $8,000/month
Calendar Updated Nov 18 2009

Property Review

Our family rented this beautiful home for the 2008/2009 winter and consider it some of the best money we have ever spent. The house feels like a secluded mountain cabin because of its amazing...
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Lake Buel acess, near Ski Butternut, Tanglewood, child and pet friendly

— Property 171589
Ski
Berkshires cottage rental
4 Bedrooms, Sleeps 7,
Cottage, lake, rural, pets considered
Rates - per property (USD)
$200/night
$1,000/week
$3,000/month
Calendar Updated Nov 18 2009

Property Review

We had a great time at this lovely house. Very clean and well-maintained. The owners were very helpful, too-- they even brought me muffin tins so I could bake during rainy weather!
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5 STAR - Berkshire Vacation Home ... Walk to beach

— Property 233290
Berkshires house rental - Sun drenched retreat all year round
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, lake, resort, terrace
Rates - per property (USD)
$2,750 - $4,000/week
$10,000 - $14,000/month
Calendar Updated Nov 18 2009

Property Review

We have rented several homes in the Berkshires before, but by far this was the best place. When we pulled up to the property all of us in the car said WOW at the same time. We rang the door bell...
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Charming Lenox Home walk to town and close to Tanglewood

— Property 185249
Berkshires house rental - Front Yard
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, rural, village, pets considered
Rates - per property (USD)
$250/night
$1,500 - $1,600/week
$2,900 - $4,600/month
Calendar Updated Nov 18 2009

Property Review

My husband and I spent several nights at this charming little house. It is freshly painted, tastefully decorated, and the kitchen is well stocked. There is a lovely little garden in the back,...
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New Contemporary Log Home with Boat Dock/Butternut Ski Basin Screened Porch

— Property 150942
Berkshires house rental
4 Bedrooms, Sleeps 9,
House, 3 Bathrooms, lake, mountain, jacuzzi
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Amazingly big beautiful home nestled in the heart of the Berkshire Mountains

— Property 201680
Berkshires house rental
6 Bedrooms, Sleeps 13,
House, 3 Bathrooms, lake, mountain, garden
Rates - per property (USD)
$200 - $250/night
$1,200/week
$3,500/month
Calendar Updated Nov 17 2009

Property Review

This was a perfect home for me and my family to have a family reunion. The second kitchen really helped in preparing the large meals we had each night. The amenities of the home added to the...
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Serenity Stone Cottage on 5 beautiful secluded acres in a historic town

— Property 190201
Berkshires cottage rental - Stone facade at cottage entrance
3 Bedrooms, Sleeps 7,
Cottage, 2 Bathrooms, mountain, town, garden
Rates - per property (USD)
$800 - $1,080/week
Calendar Updated Nov 17 2009

Property Review

The cottage was lovely. Rustic but very comfortable. We enjoyed staying here much more than we would have at a hotel or B&B. We have four children and there was room for everyone. The kids...
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'Rose Cottage' Mountain Views near Tanglewood

— Property 107229
Berkshires cottage rental
1 Bedroom, Sleeps 2,
Cottage, 1 Bathroom, mountain, rural, garden
Rates - per property (USD)
$2,000/month
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Relaxing Views, Nestled in Secluded Valley Near Tangelwood

— Property 224504
Berkshires house rental - 'ValleyView 2-Story Cape(w/Rose Cottage Apt)
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, mountain, rural, garden
Rates - per property (USD)
$2,000/month
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Tranquil Berkshire 4 Br. Cape Cottage on Big Pond

— Property 244000
Berkshires house rental - Front of Cottage
4 Bedrooms, Sleeps 8,
House, 1 Bathroom, 1 Half Bath, lake, internet access
Rates - per property (USD)
$225/night
$1,200/week
$4,400/month
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THANKSGIVING SPECIAL - 4 Nights $600 - Downtown Williamstown Cottage

— Property 169199
Berkshires house rental - Living rm (queen sleep couch), dining rm , kitchen
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, downtown, village, air-conditioning
Rates - per property (USD)
$190/night
$1,100/week
Calendar Updated Nov 17 2009

Property Review

We stayed for a four-day weekend and really enjoyed the visit, and the house added to that. We arrived to find it immaculate. Good start! The layout is very good with two-car parking that is...
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Newly Renovated Stone Cottage; Walk to Williamstown

— Property 238090
Berkshires cottage rental - Living Room
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, mountain, town, air-conditioning
Rates - per property (USD)
$125 - $250/night
$900 - $1,300/week
$2,000 - $4,000/month
Calendar Updated Nov 17 2009

Property Review

My wife and I rented the cottage for the week prior to our wedding, and our stay was everything that we had hoped it would be. In the midst of a very busy week, the cottage provided us with a...
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Amazing Spring Savings! Enjoy Lake Buel while staying in our new 2 bedroom home

— Property 148393
Berkshires house rental - Our New House
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, lake, pets considered
Calendar Updated Nov 19 2009

Property Review

My husband, toddler daughter, and I just returned from a lovely stay in the cottage. It was a perfect home for our small family. My daughter slept in her room on a trundle bed that we left low...
SPECIAL OFFER! Thanksgiving and Early Winter special! (November 22 - December 24)
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Charming Berkshires lakefront house near Jiminy Peak with beautiful views

— Property 122780
Special Offer
Berkshires house rental - The house and grounds in fall
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, lake, mountain, garden
Rates - per property (USD)
$1,800/month
Accepts Online Payments
Calendar Updated Nov 16 2009

Property Review

The property was accurately described in every respect; one of the nicest features of the house is its layout: the the cozy living/dining area and office "corner" all look out to the lake and...
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Jiminy Peak 4-Level Deluxe SKI Condo - LOOKING FOR SEASONAL WINTER RENTER

— Property 101805
Berkshires condo rental - Outside view on 24 ft. deck with Weber Gas Grill
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, mountain, resort, pool
Calendar Updated Nov 16 2009

Property Review

My family and I spent some time at this condo and could not have been happier!! The house is so warm and inviting and everything is beyond clean. There is a lot of space and the layout is just...
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The Tanglewood Suites

— Property 109031
Berkshires cottage rental - The Cottage
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, mountain, daily maid service
Calendar Updated Nov 16 2009

Property Review

We were delighted to stay in this beautiful property close to Tanglewood and the wonderful attractions of the Berkshires. When we arrived, we were warmly greeted by the owner who walked us...
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Spacious & light- Artist designed luxury & privacy in Stockbridge

— Property 170499
Berkshires house rental - Parklike setting on 3 very private acres
3 Bedrooms, Sleeps 5,
House, 2 Bathrooms, lake, mountain, garden
Rates - per property (USD)
$2,200 - $2,500/week
$6,000 - $16,000/month
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Luxurious New Colonial Home with In-ground Pool and Gorgeous Views

— Property 229406
Berkshires house rental - Westwood
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, mountain, village, pool
Rates - per property (USD)
$2,750 - $5,500/week
$4,000 - $20,000/month
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The Pastures: an Experience Not to Miss - Now with Gorgeous in-ground Pool!

— Property 186311
Berkshires estate rental - The Pastures... in Fall
6 Bedrooms, Sleeps 14,
Estate, 4 Bathrooms, 2 Half Baths, mountain, rural, sauna
Rates - per property (USD)
$9,500 - $10,000/week
$20,000 - $30,000/month
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Lenox Cottage in Woods -

— Property 130835
Berkshires cabin rental - Living Room
3 Bedrooms, Sleeps 7,
Cabin, 1 Bathroom, 1 Half Bath, lake, rural, DVD
Rates - per property (USD)
$1,000 - $1,500/week
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Bentley Brook Mountain Club at Jiminy Peak

— Property 136078
Berkshires condo rental - Bentley Brook Main Building
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, mountain, resort, jacuzzi
Rates - per property (USD)
$325 - $350/night
$2,275/week
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Charming Lakeview Home Near All Activities

— Property 137922
Berkshires cottage rental - Charming cottage overlooking lake and wetlands
3 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, lake, mountain, air-conditioning
Rates - per property (USD)
$150 - $200/night
$1,650/week
$1,150 - $6,600/month
Calendar Updated Nov 14 2009

Property Review

The location is lovely and the fall colors were great. The house is very well equipped and conducive to a comfortable stay. The only issue is that there is not a good heating source for the...