The 10 best holiday rentals in Pittsfield, USA | Booking.com
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Holiday Rentals in Pittsfield

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The best holiday rentals in Pittsfield

Check out our pick of great holiday rentals in Pittsfield

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The Cornell Inn, Lenox & The Berkshires

Lenox (Near Pittsfield)

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

M
Manuel González Iglesias
From
Spain
Common areas, staff and breakfast are amazing. Being surrounded by nature made the difference.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 559 reviews
Price from
US$138.88
1 night, 2 adults

Mountain View Suite on Jiminy Peak Ski On Off -New

Hancock (Near Pittsfield)

Boasting air-conditioned accommodation with a private pool, Mountain View Suite on Jiminy Peak Ski On Off -New is situated in Hancock.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 20 reviews
Price from
US$105
1 night, 2 adults

Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak

Hancock (Near Pittsfield)

Featuring a hot tub, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak is set in Hancock.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 9 reviews
Price from
US$397.63
1 night, 2 adults

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak

Hancock (Near Pittsfield)

Featuring air-conditioned accommodation with a private pool, Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is located in Hancock.

X
Xia
From
United States
Really nice host! We encountered a power outage for one day in the Jiminy Peak area due to a storm and the host nicely let us stay one more day without charge! That's really sweet for them. Love the room decoration and style. Have almost everything needed to cook. Near to the mountain and lifts with just a little walk.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 19 reviews
Price from
US$99.75
1 night, 2 adults

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Hancock (Near Pittsfield)

Situated in Hancock, 33 km from Cranwell Spa & Golf Club and 33 km from Tanglewood Musical Center, Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 offers a fitness centre and air conditioning.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 22 reviews
Price from
US$99.75
1 night, 2 adults

Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury

Hancock (Near Pittsfield)

Located in Hancock and only 33 km from Cranwell Spa & Golf Club, Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury provides accommodation with mountain views, free WiFi and free private...

E
Emma
From
United States
This place was a godsend. After the nearby Wyndham Resort canceled our booking last minute due to overbooking, my family was scrambling to find local accommodation. After the recent, sudden loss of my mother, my family was looking forward to our annual trip to Jiminy Peak, which was one of her favorite places. This place appeared at just the right time and was a great, even better, alternative to Wydham. Howie was a wonderful host and the accommodations were clean, comfortable, and cute. The place felt like home and had all of the amenities we needed. There were many comfortable beds and a copious number of fluffy blankets. It also had 2 bedrooms, unlike many of the other hotels in the area. Howie was very responsive to our questions and provided helpful recommendations. They even left a cute stuffed bear that we could take home as a souvenir! What a thoughtful touch. All in all, it was a wonderful stay and we would definitely stay again.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 27 reviews
Price from
US$158
1 night, 2 adults

Shaker Mill Inn

West Stockbridge (Near Pittsfield)

Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

m
meira
From
Israel
Unbelievable clean, beautiful, and outstanding place. I am very particular re cleanliness in hotel rooms so I was amazed by this outstanding suite we got. Absolutely 💯 lovely greenery around. Big windows. Kitchenette equipped with numerous products one wouldn't expect at all in a B/B. In the hallway there is a big dvd library, box games and books. We ride 🏍 it was raining all day and night, the morning we left, there were 4 towels on the bike 🏍 just for drying it before we leave!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 88 reviews
Price from
US$136
1 night, 2 adults

Harbour House Inn B&B

Cheshire (Near Pittsfield)

Featuring a garden and views of mountain, Harbour House Inn B&B is a bed and breakfast situated in a historic building in Cheshire, 31 km from Cranwell Spa & Golf Club.

C
Chady
From
France
A real traditional house very cute
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 11 reviews
Price from
US$215
1 night, 2 adults

Inn at Silver Maple Farm

East Chatham (Near Pittsfield)

Situated 19 km from Tanglewood Musical Center, 19 km from Tanglewood and 22 km from Norman Rockwell Museum, Inn at Silver Maple Farm features accommodation set in East Chatham.

A
Andrew
From
Austria
We loved the place itself.... the old barn where breakfast was served was simply amazing. But the main thing we enjoyed was the open air camp fire that was provided for the guests.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 63 reviews
Price from
US$159
1 night, 2 adults

Devonfield Inn

Lee (Near Pittsfield)

Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

L
Lesley- Ann
From
South Africa
We had the most wonderful time at this beautiful inn set in stunning surroundings and gardens. On our holiday this was the only place where we actually met and interacted with the owners , Doug and Jim. Our room was comfortable, clean and had everything we needed. Lovely leather chairs and decor. The bed was comfortable with nice linens. We were invited to the cheese and wine evening and it was great. Lovely wines and cheeses and a great way to meet other guests. We so enjoyed the piano and a few songs from Doug. Breakfast was a feast .. fruit, yogurts , eggs . Delicious and a different menu each morning. Home baked cakes .. yummy. Saturday we sat in the gardens and enjoyed a lovely afternoon of music , it was so nice to see locals join the afternoon too. We wish we could have stayed longer.. Doug and Jim you run a beautiful Inn, your commitment and hard-work tells the story. Thank you!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 13 reviews
Price from
US$369
1 night, 2 adults
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