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Resorts and apartments 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
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All 96 Rentals in Berkshires
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From
$150
Per Night
Richmond
3 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Reviews (4) Make Inquiry
From
$250
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
17 photos Details
Reviews (1) Make Inquiry
From
$250
Per Night
Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 5
10 photos Details
Reviews (2) Make Inquiry
Also consider
Fall/ Winter- Spectacular Setting-Family- Ski Sled Hike Fish Relax
3 Bedrooms, sleeps 8
$2,000 - $2,500 / week
Josiah Loomis Homestead
3 Bedrooms, sleeps 8
$250 - $325 / night
Charming Berkshires lakefront house, great views
2 Bedrooms, sleeps 5
$200 - $250 / night
Beautiful New Construction Vacation Home
4 Bedrooms, sleeps 12
$795 / night
From
$200
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
8 photos Details
Reviews (1) Make Inquiry
From
$200
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 7
16 photos Details
Reviews (4) Make Inquiry
From
$20
Per Night
North Adams
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (1) Make Inquiry
From
$375
Per Night
Lee
5 Bedrooms, 3 Bathrooms, Sleeps 11
33 photos Details
Reviews (1) Make Inquiry
From
$360
Per Night
North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (2) Make Inquiry
Get the List
From
$229
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
4 photos Details
Reviews (1) Make Inquiry
From
$200
Per Night
Hancock
4 Bedrooms, 2 Bathrooms, Sleeps 10
14 photos Details
Reviews (3) Make Inquiry
From
$155
Per Night
Lanesboro
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Reviews (12) Make Inquiry
From
$160
Per Night
North Egremont
1 Bedroom, 1 Bathroom, Sleeps 2
35 photos Details
Reviews (3) Make Inquiry
From
$125
Per Night
Becket
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details
Reviews (7) Make Inquiry
From
$500
Per Night
Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 15
19 photos Details
Reviews (7) Make Inquiry
From
$300
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (7) Make Inquiry
From
$150
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
4 photos Details
Reviews (1) Make Inquiry
From
$300
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 5
25 photos Details
Reviews (2) Make Inquiry
From
$150
Per Night
New Ashford
4 Bedrooms, 3 Bathrooms, Sleeps 7
10 photos Details
Reviews (9) Make Inquiry
From
$125
Per Night
West Stockbridge
2 Bedrooms, 1 Bathroom, Sleeps 6
5 photos Details
Reviews (2) Make Inquiry
From
$250
Per Night
West Stockbridge
5 Bedrooms, 2 Bathrooms, Sleeps 12
11 photos Details
Reviews (3) Make Inquiry
From
$250
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Reviews (2) Make Inquiry
From
$195
Per Night
Great Barrington
1 Bedroom, 1 Bathroom, Sleeps 3
10 photos Details
Reviews (7) Make Inquiry
From
$525
Per Night
Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (16) Make Inquiry
From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
35 photos Details
Reviews (89) Make Inquiry
From
$1,295
Per Week
Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (9) Make Inquiry
From
$150
Per Night
Lenox
4 Bedrooms, 1 Bathroom, Sleeps 7
21 photos Details
Reviews (15) Make Inquiry
From
$200
Per Night
West Stockbridge
4 Bedrooms, 2 Bathrooms, Sleeps 7
15 photos Details
Reviews (2) Make Inquiry
From
$150
Per Night
Monterey
3 Bedrooms, 2 Bathrooms, Sleeps 7
13 photos Details
Reviews (13) Make Inquiry
From
$100
Per Night
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
8 photos Details
Reviews (1) Make Inquiry
From
$195
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (19) Make Inquiry
From
$75
Per Night
Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
Reviews (6) Make Inquiry
From
$2,450
Per Week
Richmond
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Make Inquiry
From
$125
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
10 photos Details
Make Inquiry
From
$1,250
Per Week
Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Make Inquiry
From
$350
Per Night
Becket
3 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Make Inquiry
From
$135
Per Night
Becket
2 Bedrooms, 2 Bathrooms, Sleeps 4
6 photos Details
Make Inquiry
From
$250
Per Night
Granville
5 Bedrooms, 3 Bathrooms, Sleeps 12
5 photos Details
Make Inquiry
From
$200
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
11 photos Details
Make Inquiry
From
$1,050
Per Week
Becket
3 Bedrooms, 1 Bathroom, Sleeps 5
9 photos Details
Make Inquiry
From
$175
Per Night
South Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Make Inquiry
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Book Online(77)
Use filters to find the best results!

Suitability

  • Wheelchair access (13)
  • Elder access (46)
  • Suitable for children (68)
  • Pet friendly (28)
  • Smoking allowed (2)

Amenities

  • Internet (72)
  • Other outdoor space (71)
  • Parking (59)
  • Grill (58)
  • Washer/Dryer (55)
  • View all amenities
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Book Online(77)

Suitability

  • Wheelchair access (13)
  • Elder access (46)
  • Suitable for children (68)
  • Pet friendly (28)
  • Smoking allowed (2)

Amenities

  • Internet (72)
  • Other outdoor space (71)
  • Parking (59)
  • Grill (58)
  • Washer/Dryer (55)
  • View all amenities