Berkshires Vacation Rentals

Welcome to Berkshires. Scroll down this page to find your favorite travel destination in Berkshires and browse our extensve inventory of accommodations in Berkshires. Leisure travelers planning their family vacations can get offers directly from owners of Berkshires vacation homes or houses in Berkshires. Sometimes these single rental units are referred to as Berkshires cabins or Berkshires villas. Other popular lodging options include vacation rentals in Berkshires, Berkshires apartments and condos in Berkshires. For business travelers we offer several convenient hotels in Berkshires or small boutique hotels in Berkshires area, many with the ability to book online. If you are planning a romantic getaway in Berkshires, we highy recommend our unique inventory of bed and breakfasts in Berkshires. B&Bs can also referred as small country inns in Berkshires.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at we make it easy for travelers to find best Berkshires vacation rentals using our free inquiry service or Berkshires lodging locator service. Save time searching for Berkshires rental vacations and Berkshires accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Berkshires vacation home rentals owners as well as from Berkshires resorts, Berkshires cabin rentals, and Berkshires vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Massachusetts area. Our engine will match your specific inquiry criteria with each Berkshires vacation rental listing, Berkshires vacation house or Berkshires villa in our Berkshires rental vacations inventory. Finding Berkshires vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Berkshires accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Berkshires lodging in Massachusetts.

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

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ID: 345229
Berkshires Vacation Rental - Vacation Rental in Berkshires
From USD90 nt
3 Bedrooms
Sleeps 8
3 + bedroom home overlooking pontoosuc lake. The house offer a full kitchen,living room,dining room and 1 and 1/2 bathrooms. there is a finished basement with a pooltable and a fireplace. washer,dryer ...Read Full Description
ID: 89434
Architect designed white clapboard vacation house - Vacation Rental in Berkshires
5 Bedrooms
Sleeps 10
5 bedroom semi traditional architect designed white clapboard berkshires vacation house with pool and pool deck. Fully furnished and equipped, open living room and two storey dining room. separate stu ...Read Full Description
ID: 127
Berkshire Resort Rental - Vacation Rental in Berkshires
1 Bedrooms
Sleeps 4
All seasons privately owned studio unit situated at bentley brook mountain club adjacent to jiminy peak - the mountain resort in hancock, massachusetts. Situated in the berkshire hills region of weste ...Read Full Description
ID: 5982
 Austerlitz  private romantic waterfront cottage - Vacation Rental in Berkshires
Sleeps 2
Off season special: 3 or more nights $150 a night including all fees. $700 a week. A long private driveway off a dirt road leads to a spectacular berkshire rental on a seven acre estate .the cottage o ...Read Full Description
ID: 20950
Berckhouse in the Berkshires:   Vacation Rental - Vacation Rental in Berkshires
3 Bedrooms
Sleeps 6
Spectacular contemporary saltbox in the berkshires on 18 wooded acres one mile down the road from jacob's pillow, the internationally famous dance theater center in becket, mass. Magical setting with ...Read Full Description
ID: 20967
Berkshires Vacation Home Rental - Vacation Rental in Berkshires
3 Bedrooms
Sleeps 6
Post and beam house with a small creek near jiminy peak. Located on a private road, beautifully furnished with antiques, and mountain views from every window....huge fireplace, deck, well appointed ki ...Read Full Description
ID: 345532
Townhouse in Oak N Spruce Resort- 7/16 - 7/23 - Vacation Rental in Berkshires
From USD800 wk
2 Bedrooms
Sleeps 6
This professionally managed resort is located in the beautiful berkshire hills of western massachusetts. Guests can enjoy the peaceful beauty of the berkshires at the oak n spruce resort, set amid 200 ...Read Full Description
ID: 97550
Round House - Berkshires Rental - Vacation Rental in Berkshires
From USD250 nt
3 Bedrooms
Sleeps 6
Enjoy the beautiful 3 bedroom, 2 bath home, located in becket, ma, which is set on 2 acres of land in the midst of nature. From the 2 car garage, you walk into a bright foyer, where you can kick off y ...Read Full Description
ID: 336909
Berkshire Comfort inn - Hotel in Berkshires
1 Bedrooms
Sleeps 2
Situated in the heart of massachusetts’ berkshire mountains, the comfort inn & suites is an upscale hotel offering upscale accommodations for great barrington vacations, weekend getaways and busin ...Read Full Description
ID: 202810
3 Bedrooms
Sleeps 8
West stockbridge---three acres of perennial gardens, woodlands, meadow and babbling brook awaits your enjoyment with tom ball mountain in the back yard of this berkshires vacation rental. Ski, ski, sk ...Read Full Description
ID: 20781
1897 Hampton Terrace Bed and Breakfast - Bed and Breakfast in Berkshires
1 Bedrooms
Sleeps 2
the berkshire hills. First they attracted the literary and artistic elite. henry wadsworth longfellow, mark twain, herman melville, nathaniel hawthorne, daniel webster, edith wharton, daniel chester ...Read Full Description
ID: 303715
Lakeside Terrace B&B - Bed and Breakfast in Berkshires
Lakeside terrace has 7 rooms and is right on lake garfield in monterey. Beautiful swimming, kayaking, and fishing. close to stockbridge, great barrington and lenox.... ...Read Full Description
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Smart Search

*Traveling Dates:

Flexible Dates
1+ (11)
3+ (8)
6+ (7)

(vacation rentals only)
1 (3)
2 (1)
3 (5)
4+ (1)

Vacation Rental Types:
Apartment (1)
Cottage (1)
Farm (1)
Home (3)
Townhouse (1)

Lodging Types:
Bed and Breakfasts (2)
Hotels (1)
Vacation Rentals (9)

Location Attributes:
Near water (1)
Lakefront (1)
Near beach (1)

TV/VCR (6)
Utensils (6)
Full Kitchen (6)
Linens provided (5)
BBQ (6)
Fireplace (5)

Things To Do:
Tennis (5)
Restaurants (7)
Biking (6)
Horseback Riding (5)
Camping & Hiking (4)
Swimming (5)

Special Features:
Children Welcome (12)
Smoking Permitted (6)
Pet friendly (8)
Handicap accesibility (11)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Great Barrington (6)
Stockbridge (3)
South Lee (1)
Lenox (15)
Lee (4)
Sheffield (1)
Pittsfield (7)
Hudson (1)

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