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Holiday Homes and Apartments Pittsfield, MA and nearby

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All 44 Rentals in the Pittsfield Area
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From
$114
Per Night
1 Bedroom, 1 Bathroom, Sleeps 5
Shared Indoor Pool, Washer, Dryer & more
8 photos Details Reviews (1) Make Enquiry
From
$196
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details Make Enquiry
From
$149
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Washer, Mountain Views, Satellite TV & more
20 photos Details Make Enquiry

The following rentals are within 15 kilometres of Pittsfield, Massachusetts.

From
$82
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Sauna, Safe, Washer & more
27 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 19 September 2014
What a pleasant and wonderful stay. This is the second Wyndham resort we have stayed at. We had asked for a room on the top floor with a view and that was exacly what we got...
4 of 5 stars Reviewed 19 August 2014
The condo has a full kitchen and living room, making it pleasant to gather with family and/or friends in the evening or on a rainy day.
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From
$343
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Shared Indoor Pool, Housekeeping Optional & more
12 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 21 July 2014
The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although...
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From
$400
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Internet Access, Dryer, Washer & more
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 June 2014
I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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From
$126
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Grill, Internet Access, Air Conditioning & more
11 photos Details Reviews (4) Make Enquiry
From
$343
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 5
Fireplace, Satellite TV, Washer & more
25 photos Details Reviews (2) Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Internet Access, Grill, Washer & more
11 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 18 June 2013
This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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From
$172
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
4 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 June 2014
And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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From
$200
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Mountain Views, Internet Access & more
10 photos Details Reviews (12) Make Enquiry
5 of 5 stars Reviewed 8 July 2014
We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
5 of 5 stars Reviewed 31 May 2014
We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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From
$262
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Grill, Air Conditioning, Dryer & more
4 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 12 August 2013
Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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From
$257
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Washer, Hot Tub, Grill & more
14 photos Details Reviews (3) Make Enquiry
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Mountain Views, Fireplace, Grill & more
8 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 June 2014
We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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From
$429
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
Dryer, Grill, Internet Access & more
33 photos Details Reviews (8) Make Enquiry
4 of 5 stars Reviewed 28 September 2014
We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
5 of 5 stars Reviewed 3 September 2014
This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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From
$172
Per Night
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Washer, Dryer, Grill & more
21 photos Details Reviews (16) Make Enquiry
5 of 5 stars Reviewed 6 September 2014
Spent a late summer weekend with my grown children and their friends. The Gartner House had plenty of room for us to relax and spread out. The rooms were old but charming and...
4 of 5 stars Reviewed 10 February 2014
We stayed at the Gartner House in the middle of winter. The house is comfy and well appointed. The kitchen has every thing you would need. The record player and variety of records...
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From
$315
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Indoor Pool, Satellite TV & more
18 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 2 August 2013
Really nice accommodations & the staff was amazing, going out of their way to help in any way possible. Easy access to Jiminy Peak, which was full of activities for the...
5 of 5 stars Reviewed 31 January 2013
We spent time at Bentley Brook with "Kids" and the "Grands". Loved the 2BR, 2B with full K and really nice LR. Immaculate, extremely well equipped and spacious. The convenience...
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From
$86
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Mountain Views, Washer, Satellite TV & more
25 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 13 October 2014
Stayed here for a couple nights over labor day to get out of the city. The place is perfect for a group of 4 and even better for our 2 dogs. Great little creek for them to go...
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From
$160
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Water Views, Balcony, Housekeeping Optional & more
7 photos Details Reviews (1) Make Enquiry
2 of 5 stars Reviewed 11 September 2014
I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The...
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From
$180
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details Make Enquiry
From
$343
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details Make Enquiry
From
$149
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
Booking
Safe, Dryer, Garden & more
8 photos Details Make Enquiry
From
$286
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Washer, Grill, Fireplace & more
7 photos Details Make Enquiry
From
$229
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
Air Conditioning, Dishwasher, Internet Access & more
19 photos Details Make Enquiry
From
$114
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Satellite TV, Washer, Dryer & more
4 photos Details Make Enquiry
From
$572
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Hot Tub, Dryer, Washer & more
18 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Housekeeping Optional, Mountain Views, Dishwasher & more
12 photos Details Make Enquiry
From
$166
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
Satellite TV, Garden, Internet Access & more
16 photos Details Make Enquiry
From
$515
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Pool, Garden, Internet Access & more
20 photos Details Make Enquiry
From
$257
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Satellite TV, Dryer, Garden & more
19 photos Details Make Enquiry
From
$153
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details Make Enquiry
From
$172
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details Make Enquiry
From
$458
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Private Indoor Pool, Water Views & more
24 photos Details Make Enquiry
From
$143
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Internet Access, Balcony, Garden & more
10 photos Details Make Enquiry
From
$277
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Internet Access, Air Conditioning, Dishwasher & more
15 photos Details Make Enquiry
From
$858
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 12
7 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details Make Enquiry
From
$257
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Shared Indoor Pool, Internet Access, Dishwasher & more
11 photos Details Make Enquiry
From
$205
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Shared Indoor Pool, Internet Access, Sauna & more
16 photos Details Make Enquiry
From
$429
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Indoor Pool, Satellite TV, Sauna & more
5 photos Details Make Enquiry
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Air Conditioning, Internet Access, Grill & more
12 photos Details Make Enquiry
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
7 photos Details Make Enquiry
From
$200
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
2 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Washer, Internet Access, Housekeeping Optional & more
10 photos Details Make Enquiry
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Suitability

  • Wheelchair access (6)
  • Elder access (15)
  • Suitable for children (31)
  • Pet friendly (11)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (32)
  • Internet (30)
  • Washer/Dryer (28)
  • Grill (23)
  • Parking (23)
  • View all amenities
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