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Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsfield holiday homes

Outdoor dining

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$767
includes taxes & fees
3 Sept - 4 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

2. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,544
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
Private kitchen

3. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AU$331
includes taxes & fees
10 Sept - 11 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
Living area

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$314
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley
Pool

5. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is AU$754
includes taxes & fees
2 Sept - 3 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Private kitchen

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AU$784
includes taxes & fees
6 Sept - 7 Sept
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Living area

7. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.6 out of 10, Exceptional, (7 reviews)
The price is AU$556
includes taxes & fees
14 Sept - 15 Sept
stylish Berkshires Retreat
Exterior

8. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$753
includes taxes & fees
15 Sept - 16 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Interior

9. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AU$398
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Interior

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$509
includes taxes & fees
15 Sept - 16 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

11. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$536
includes taxes & fees
8 Sept - 9 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

12. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$437
includes taxes & fees
3 Sept - 4 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

13. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$437
includes taxes & fees
8 Sept - 9 Sept
Cozy Riverside Berkshires Retreat
Dining

14. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AU$317
includes taxes & fees
12 Sept - 13 Sept
Cozy Home in Pownal VT
Outdoor dining

15. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$732
includes taxes & fees
14 Sept - 15 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
Lobby

16. Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
10.0 out of 10, Exceptional, (6 reviews)
"The home was great! It was tucked away but still very close to everything! Our family enjoyed our stay and Michelle was very welcoming and had everything at the house for us to feel comfortable."
United States
Jon U.
The price is AU$1,410
includes taxes & fees
4 Sept - 5 Sept
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
Private kitchen

17. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AU$553
includes taxes & fees
3 Sept - 4 Sept
Home in Great Barrington
Property grounds

18. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is AU$477
includes taxes & fees
20 Sept - 21 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Living area

19. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AU$795
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
Room

20. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
Stylish Mid-century Modern Berkshires Cape
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Enjoyed my stay! Spacious rooms, clean, quiet, surrounded by nature, free custom coffee ☕️ in lobby, free laundry facilities (bring your own detergent), no restaurant on-site. Pittsfield had lots of dining options nearby. I recommend the local nature trails at the Audubon Sanctuary, so beautiful 😍"
Michelle 3-night trip
Posted 12 hours ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
149
Accommodation
418 Holiday Homes
Lowest Price
AU$314
Highest Price
AU$1,544