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  • Showing 1-50 of 300+
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Exceptional! 5.0/5
(10 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 14
House #345355
10
Viewed 15 times in the last 48 hours
Exceptional! 5.0/5
(10 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 14
House #259766vb
10
Wonderful! 4.8/5
(24 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #340808
24
Viewed 15 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 20
Chalet #640519vb
2
Viewed 14 times in the last 48 hours
Exceptional! 5.0/5
(6 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 10
House #129127vb
6
Viewed 13 times in the last 48 hours
Excellent! 4.7/5
(12 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 12
House #334430
12
Viewed 12 times in the last 48 hours
Wonderful! 4.8/5
(12 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 12
House #622687vb
12
Viewed 13 times in the last 48 hours
Excellent! 4.7/5
(11 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Chalet #3642810
11
Viewed 7 times in the last 48 hours
Wonderful! 4.9/5
(57 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 15
House #148104vb
57
Viewed 43 times in the last 48 hours
Wonderful! 4.8/5
(21 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 10
House #166942vb
21
Viewed 19 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
House #429854vb
9
Viewed 5 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 8
Condo #868730vb
4
Viewed 30 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 11
House #759492vb
1
  • 5 BR
  • 3 BA
  • Sleeps 16
Condo #938633
2
  • 3 BR
  • 3 BA
  • Sleeps 6
House #764994vb
  • 4 BR
  • 2 BA
  • Sleeps 8
House #3861821
Excellent! 4.7/5
(9 reviews)
View details for price
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 6
House #4328487
9
Exceptional! 5.0/5
(97 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 5
Cabin #176037
97
Viewed 107 times in the last 48 hours
Excellent! 4.6/5
(5 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
Condo #104286
5
Viewed 62 times in the last 48 hours
Wonderful! 4.8/5
(39 reviews)
avg/night
  • 5 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 13
House #119086
39
Viewed 47 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 4
Condo #846796vb
4
Viewed 49 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Cabin #754153vb
9
Viewed 48 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #4053247
2
Viewed 16 times in the last 48 hours
Wonderful! 4.9/5
(35 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 10
House #3809315
35
Viewed 13 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #628992vb
3
Viewed 27 times in the last 48 hours
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #3840565
Viewed 23 times in the last 48 hours
Excellent! 4.5/5
(15 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #104116
15
Viewed 21 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
Cottage #4272059
3
Viewed 21 times in the last 48 hours
Excellent! 4.7/5
(85 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #374633vb
85
Viewed 19 times in the last 48 hours
Exceptional! 5.0/5
(19 reviews)
avg/night
  • 2 BR
  • 1 BA
  • Sleeps 4
Cabin #401479vb
19
Viewed 16 times in the last 48 hours
Exceptional! 5.0/5
(23 reviews)
avg/night
  • 7 BR
  • 4 BA
  • Sleeps 24
Farmhouse #3839959
23
Viewed 47 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 8
Cottage #3929442
9
Viewed 22 times in the last 48 hours
Wonderful! 4.9/5
(16 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #758489vb
16
Viewed 8 times in the last 48 hours
Excellent! 4.6/5
(15 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 18
House #112754
15
Viewed 38 times in the last 48 hours
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 7
House #495543vb
4
Viewed 5 times in the last 48 hours
Exceptional! 5.0/5
(31 reviews)
avg/night
  • 2 BR
  • 3 BA
  • Sleeps 6
House #411999vb
31
Viewed 7 times in the last 48 hours
Wonderful! 4.8/5
(12 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 18
House #4086336
12
Viewed 64 times in the last 48 hours
Exceptional! 5.0/5
(52 reviews)
$95
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Apartment #354330
52
Viewed 25 times in the last 48 hours
Exceptional! 5.0/5
(15 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
House #3992583
15
Viewed 46 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 5 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 13
House #853465vb
9
Viewed 23 times in the last 48 hours
Wonderful! 4.8/5
(9 reviews)
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
Condo #4225962
9
Viewed 35 times in the last 48 hours
Wonderful! 4.8/5
(39 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #128197
39
Viewed 33 times in the last 48 hours
Wonderful! 4.9/5
(13 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
Lodge #432099vb
13
Viewed 10 times in the last 48 hours
Excellent! 4.7/5
(10 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 10
Chalet #478821vb
10
Viewed 19 times in the last 48 hours
Excellent! 4.5/5
(19 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #264900
19
Viewed 22 times in the last 48 hours
Wonderful! 4.9/5
(8 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #967638vb
8
Viewed 19 times in the last 48 hours
Wonderful! 4.9/5
(39 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 12
House #211351
39
Viewed 22 times in the last 48 hours
Exceptional! 5.0/5
(24 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 14
Lodge #263450vb
24
Viewed 20 times in the last 48 hours
Excellent! 4.4/5
(5 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Condo #268757vb
5
Viewed 6 times in the last 48 hours
Wonderful! 4.8/5
(16 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 12
Chalet #788299vb
16
Viewed 22 times in the last 48 hours
  • 1 - 50 of 300+

Pittsfield: Vacation Rentals (601)

 

Recent Pittsfield Reviews

Quiet and charming

5 of 5
My girlfriend and I had a very relaxing stay with our dogs. The movie projector and hot tub was great!
  • Submitted: Feb 15, 2017
  • Stayed: Feb 2017

Perfect House for Large Groups

5 of 5
Honestly, I was hesitant to rent this house based on the other review but it could not have been more wrong. We did get spotty service while using our navigation on the way to the house, however, the directions the rental office gave were very detailed and we made it there with no problems (it's just a few minutes off the main road and honestly, you're in the mountains so it's to be expected). The house is fairly secluded but we all considered this to be a plus and couldn't wait to enjoy the beautiful view the house offered from the outdoor hot tub. We chose the house so we could spend Saturday skiing at Killington since it is only a 10 minute drive from the house. The layout of the house was also great for our large group since the living area, dining room and kitchen are all open and we were all able to sleep very comfortably. I even hope to book the house again next year. If you're looking for a house for a large group you can't get much better than this.
  • Submitted: Feb 13, 2017
  • Stayed: Feb 2017

Ski Getaway

5 of 5
The condo offered was perfect for our group of 6. It allowed us to sleep comfortably, cook when needed, and be very close to Killington's slopes. Dennis was also very responsive whenever we had questions regarding our stay. We would happily stay again for our next years ski trip.
  • Submitted: Feb 13, 2017
  • Stayed: Feb 2017