We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Villas in Berkshires, MA

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 93 Rentals in Berkshires
loading...
Sort by
From
£204
Per Night
Great Barrington
5 Bedrooms, 3 Bathrooms, Sleeps 11
9 photos Details
Make Enquiry
From
£175
Per Night
Becket
3 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Make Enquiry
From
£336
Per Night
Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 5
5 photos Details
Make Enquiry
Also consider
Berkshires- 2014 Summer Rental July And August
3 Bedrooms, sleeps 8
£1,752 / month
Beautiful New Construction Vacation Home
4 Bedrooms, sleeps 12
£464 / night
Berkshires Rental 15 minutes to Tanglewood
2 Bedrooms, sleeps 6
£102 / night
Wyndham Bentley Brook at Jiminy Peak
2 Bedrooms, sleeps 6
£117 - £175 / night
From
£730
Per Week
Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Make Enquiry
From
£175
Per Night
Lenox
2 Bedrooms, 1 Bathroom, Sleeps 4
7 photos Details
Make Enquiry
From
£234
Per Night
Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
24 photos Details
Make Enquiry
From
£161
Per Night
Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Make Enquiry
From
£117
Per Night
Cheshire
2 Bedrooms, 1 Bathroom, Sleeps 5
19 photos Details
Make Enquiry
Get the List
From
£292
Per Night
Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
Make Enquiry
From
£102
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
7 photos Details
Make Enquiry
From
£76
Per Night
Pittsfield
3 Bedrooms, 1 Bathroom, Sleeps 8
20 photos Details
Make Enquiry
From
£82
Per Night
North Adams
2 Bedrooms, 1 Bathroom, Sleeps 4
16 photos Details
Make Enquiry
From
£117
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Make Enquiry
From
£117
Per Night
Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Make Enquiry
From
£105
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Make Enquiry
From
£175
Per Night
Monterey
4 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
Make Enquiry
From
£175
Per Night
Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 9
11 photos Details
Make Enquiry
From
£117
Per Night
Becket
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Make Enquiry
From
£438
Per Night
Lee
5 Bedrooms, 5 Bathrooms, Sleeps 12
7 photos Details
Make Enquiry
From
£1,431
Per Week
Richmond
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Make Enquiry
From
£117
Per Night
Great Barrington
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
Make Enquiry
From
£175
Per Night
Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Make Enquiry
From
£175
Per Night
Lenox
3 Bedrooms, 3 Bathrooms, Sleeps 7
33 photos Details
Make Enquiry
From
£1,168
Per Week
Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
Make Enquiry
From
£117
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Make Enquiry
From
£2,628
Per Week
Great Barrington
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details
Make Enquiry
From
£117
Per Night
Stockbridge
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Make Enquiry
From
£146
Per Night
Tyringham
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details
Make Enquiry
From
£350
Per Night
Tyringham
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
Make Enquiry
From
£102
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
2 photos Details
Make Enquiry
From
£73
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
10 photos Details
Make Enquiry
From
£44
Per Night
Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
Reviews (6) Make Enquiry
From
£210
Per Night
North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (2) Make Enquiry
From
£88
Per Night
New Ashford
4 Bedrooms, 3 Bathrooms, Sleeps 7
10 photos Details
Reviews (7) Make Enquiry
From
£146
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Make Enquiry
Go to map view
Book Online(77)
Use filters to find the best results!

Suitability

  • Wheelchair access (12)
  • Elder access (45)
  • Suitable for children (66)
  • Pet friendly (28)
  • Smoking allowed (2)

Amenities

  • Internet (69)
  • Other outdoor space (68)
  • Parking (56)
  • Grill (55)
  • Washer/Dryer (55)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List