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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Lake Home on Stockbridge Bowl

— Property 232583
Berkshires house rental - Property exterior
2 Bedrooms, Sleeps 6,
House, 3 Bathrooms, lake, rural, air-conditioning
Rates - per property (USD)
$1,000/week
$4,000/month
Calendar Updated Nov 8 2009

Property Review

The house was even better than the description--very clean, beautifully lit, bigger than it looks. All the details were taken care of, from the welcoming and instructional letter we found when we...
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Jiminy Peak Mountainside Condo

— Property 224073
Berkshires condo rental
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, mountain, resort, pool
Calendar Updated Nov 8 2009

Property Review

We rented this place for 2 weeks and had a wonderful time. We are a family and the kids ranged in age from 3-10. The condo is beautifully decorated but also homey and comfortable. The bedrooms...
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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 8 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...
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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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Mill Brook House by the Bissell Bridge

— Property 144555
Berkshires house rental - Mill Brook House
1 Bedroom, Sleeps 6,
House, 1 Bathroom, mountain, river, garden
Rates - per property (USD)
$100 - $125/night
$650 - $700/week
$2,000/month
Calendar Updated Nov 7 2009

Property Review

To be honest, I was a little skeptical about the size of this house. But we were taken aback when we arrived! The outside could use some maintenance but the inside was immaculate and cozy, yet...
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Book for WINTER SKI SEASON **Special ALL Season Rate**

— Property 135954
Berkshires cottage rental - Luxury Loaded Just Pack Your Bags and Enjoy!!!
1 Bedroom, Sleeps 4,
Cottage, 1 Bathroom, mountain, river, garden
Rates - per property (USD)
$100 - $200/night
$600 - $650/week
$2,600/month
Calendar Updated Nov 6 2009

Property Review

This is a clean, comfortable, well maintained cottage. The location is ideal. It would be crowded with more than 2 adults. The owners are super! We repeat year after year. I would highly recommend...
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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 6 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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Cozy Farmhouse, walk to campus and downtown

— Property 228968
Berkshires farmhouse rental - Front of house
3 Bedrooms, Sleeps 5,
Farmhouse, 1 Bathroom, 1 Half Bath, mountain, town, garden
Rates - per property (USD)
$145 - $250/night
$950 - $1,300/week
Calendar Updated Nov 6 2009

Property Review

I spent a week at this house and loved it. 5 min walk to town/campus/theater, on a very quiet street with a rushing stream, the house is a charming wood beamed farmhouse with every amenity a...
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Luxurious Secluded Hilltop Carriage House

— Property 100299
Berkshires house rental - Front view of the House
3 Bedrooms, Sleeps 10,
House, 2 Bathrooms, mountain, river, garden
Rates - per property (USD)
$250 - $400/night
$2,000 - $2,500/week
$6,000 - $8,000/month
Calendar Updated Nov 6 2009

Property Review

We had a wonderful week at the Carriage House. The location is perfect. The house is very comfortable, especially the main room, and the large, well-furnished deck is terrific--we ate many meals...
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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 8 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...
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 8 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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'Village View'- Spacious, Secluded 1890's Lenox Village Gem

— Property 156305
Berkshires house rental - Winter in The Berkshires
5 Bedrooms, Sleeps 9,
House, 3 Bathrooms, mountain, village, jacuzzi
Rates - per property (USD)
$2,300 - $3,500/week
$13,000/month
Calendar Updated Nov 7 2009

Property Review

My family and I spent three nights at the house in October and had a lovely stay. We had our two small boys, ages 3 and 1, and the home was very child friendly (Carol even had some safety gates at...
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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 6 2009

Property Review

I stayed at the cabin last summer and enjoyed it immensely. It was everything the ad promised and more. Clean, comfortable, secluded but not lonely.The carpet of stars visible from the yard at...
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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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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 5 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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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 5 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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Idyllic Berkshire Get Away: Balance of relaxation and convenience

— Property 237215
Berkshires house rental - A view of the side of the house from the driveway
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, town, garden
Rates - per property (USD)
$700/week
$2,000 - $2,700/month
Accepts Online Payments
Calendar Updated Nov 4 2009

Property Review

I stayed here for a weekend with my boyfriend and the house is very spacious and well-kept, so it would be fun to go back again with a big group of friends to take advantage of the space and...
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Spacious Contemporary - Country Mountains - Walk to Town - All Seasons.

— Property 139379
Berkshires house rental
3 Bedrooms, Sleeps 7,
House, 3 Bathrooms, mountain, rural, pets considered
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Berkshire Sanctuary: Apartment Suite in The Carriage House

— Property 122925
Berkshires apartment rental
1 Bedroom, Sleeps 2,
Apartment, 1 Bathroom, rural, town, air-conditioning
Rates - per property (USD)
$125/night
$600/week
$1,400/month
Calendar Updated Nov 4 2009

Property Review

Accessible to the town, but still with a great secluded feel. A very welcoming owner, dog and two cats who make you feel as though you were brought up there. Immaculate while keeping New England...
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Jiminy Peak: The place to **Stay** and **Enjoy**...2/2 in the Berkshires

— Property 145038
Berkshires townhome rental - Photo merge of living room
2 Bedrooms, Sleeps 6,
Townhome, beach, mountain, pool
Rates - per property (USD)
$160 - $378/night
$900 - $1,240/week
$1,800 - $2,800/month
Calendar Updated Nov 3 2009

Property Review

We spent a few days before Thanskgiving and found the place to be peaceful, clean and restorative as we traveled from seeing our New York Family before to Boston family after. We took...
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Sip wine by a warm fire Find Romance, Relaxation, in this Cozy Log cabin

— Property 131221
Berkshires cabin rental - Welcome to Wisteria Cottage
1 Bedroom, Sleeps 2,
Cabin, 1 Bathroom, lake, mountain, TV
Rates - per property (USD)
$140 - $150/night
$850/week
$2,000/month
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Five Bedroom /Four Season Relaxing House

— Property 125683
Berkshires house rental
5 Bedrooms, Sleeps 10,
House, 2 Bathrooms, lake, mountain, jacuzzi
Rates - per property (USD)
$250 - $450/night
$2,500/week
$8,000/month
Calendar Updated Nov 3 2009

Property Review

We spent a week at the house in the winter. It worked well for us, our children, their spouses and 2 babies. The house is very clean, well-equipped and very well located. Owners were terrific.
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Beautiful New Lindal Cedar Home with Great Lake Views

— Property 156700
Berkshires house rental - Front of House
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, lake, TV
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Log Home Nestled in the Woods

— Property 162300
Berkshires chalet rental - Summer at the Chalet
4 Bedrooms, Sleeps 7,
Chalet, 2 Bathrooms, mountain, rural, balcony
Rates - per property (USD)
$1,400 - $1,500/week
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Elegant, spacious home in the heart of town, has private deck/yard, WiFi, cable.

— Property 263291
Berkshires house rental - Living Room
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, downtown, mountain, internet access
Rates - per property (USD)
$175 - $225/night
$800 - $1,300/week
$2,000 - $4,000/month
SPECIAL OFFER! CHRISTMAS WEEK SPECIAL (December 24 - January 2)
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Beautiful Spacious Wooded Home

— Property 319198
Special Offer
Berkshires house rental - Property exterior
4 Bedrooms, Sleeps 12,
House, 2 Bathrooms, 1 Half Bath, TV, DVD
Rates - per property (USD)
$185/night
$1,200/week
$4,000/month
Calendar Updated Nov 1 2009

Property Review

Roberta: Really enjoyed our stay last Fall. Your home is very well kept and we loved your walls of photo's. Everything about it was how you described.
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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 5 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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Lovely Lenox Colonial with mountain views yet one mile from center of town

— Property 174313
Berkshires house rental - Front of house
4 Bedrooms, Sleeps 9,
House, 2 Bathrooms, 1 Half Bath, mountain, rural, jacuzzi
Rates - per property (USD)
$475/night
$2,000 - $3,500/week
$11,000/month
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THANKSGIVING ON YOUR OWN PRIVATE LAKE

— Property 224680
Berkshires house rental - Warm and Cozy
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, lake, mountain, garden
Rates - per property (USD)
$500/night
$2,000/week
Calendar Updated Nov 4 2009

Property Review

The house and setting are both spectacular. The house is thoughtfully designed, clean and replete with amenities and features required by a family to make for a comfortable, enjoyable and...
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Beautiful, cedar interior & exterior with sauna & hot tub nestled on 5 acres

— Property 257798
Berkshires house rental
5 Bedrooms, Sleeps 10,
House, 3 Bathrooms, downtown, mountain, sauna