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Our top choices for Pittsfield holiday homes

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, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,464
HK$4,311 total
includes taxes & fees
10 Aug - 11 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 HK$5,757
HK$10,064 total
includes taxes & fees
11 Aug - 12 Aug
Hancock Village Inn Near Jiminy Peak

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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is HK$565
HK$1,647 total
includes taxes & fees
10 Aug - 11 Aug
NEW RENO - Chalet-style farm loft near Tanglewood

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 HK$1,035
HK$2,162 total
includes taxes & fees
7 Sept - 8 Sept
1800s Carriage house in Berkshires / Hudson Valley

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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 HK$2,133
HK$4,387 total
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley

6. White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is HK$5,647
HK$9,037 total
includes taxes & fees
8 Aug - 9 Aug
White Lily Lodge 50 acre estate with private lake

7. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,380
HK$4,397 total
includes taxes & fees
9 Aug - 10 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,673
HK$3,543 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$839
HK$2,812 total
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it

10. 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 HK$1,380
HK$4,382 total
includes taxes & fees
9 Aug - 10 Aug
Comfortable Berkshires retreat on mtn resort, SISO

11. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (9 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
The price is HK$2,314
HK$4,670 total
includes taxes & fees
10 Aug - 11 Aug
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

12. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 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 HK$911
HK$1,617 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Home in Pownal VT

13. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is HK$2,769
HK$5,187 total
includes taxes & fees
12 Aug - 13 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

14. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,506
HK$3,409 total
includes taxes & fees
7 Sept - 8 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

15. 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 HK$1,475
HK$3,374 total
includes taxes & fees
7 Sept - 8 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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 HK$1,373
HK$2,497 total
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.

17. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (22 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 HK$1,751
HK$2,691 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat

18. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,541
HK$4,950 total
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups

19. Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"good"
United States
Ismael
Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (36 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$2,118
HK$3,207 total
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
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

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
169
Accommodation
449 Vacation Homes
Lowest Price
HK$1,617
Highest Price
HK$10,064

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