Pittsfield Cottages from CA $777

A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield cottages

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

CA $777 total

includes taxes & fees

Jul 21 - Jul 22

Beachwood Cottage

Stockbridge

Christine P.

CA $894 total

includes taxes & fees

Aug 6 - Aug 7

Berkshires farm, 30+ guests, 50 acres

New Lebanon

CA $3,581 total

includes taxes & fees

Aug 5 - Aug 6

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Top Pittsfield Hotel Reviews

Berkshire Inn

10/10 Excellent

"At a good price, it offered a pleasant stay."

Berkshires Untold

8/10 Good

"Its an interesting experience in that we thought we were staying at a hotel/ inn. The pictures and the website lead one to believe that but when we got there, we saw a motel. Nothing wrong with that but we felt we had been misinformed. They push the pcitures of the Club room which looks like an inn/ restaurant but that is the front of the building but attached to it is the motel where you stay. Again, once we knew that, we were fine but honestly, we were looking for more of an Inn or a hotel/ inn. It comes over as a glorified motel. The staff is wonderful and the Club room is a nice addition but I really thought the advertising was duplicitous. We were talking to a friend about it and she agreed that she also felt misled. I'm not sure that they have to do this but I guess if you put motel, you wouldn't get as much interest nor could you charge the same? Other than that, no comment."

The Yankee Inn

10/10 Excellent

"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."

The Red Lion Inn

8/10 Good

"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."

FairBridge Inn Express

8/10 Good

"Room was clean and in excellent condition - apparently they have totally renovated since earlier reviews that mentioned severe problems. The exterior could use some paint, but the room was perfectly clean and fairly spacious. All the little things, like good A/C, shower temp/pressure, a working mini-fridge, etc., were completely fine. Complaints: I couldn't get the WiFi to work. Also: it's not in the most scenic part of Pittsfield, but it's just minutes from the nicer areas, and a short walk to fast food or decent chain restaurants like Friendlys, Applebees, and Starbucks."

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Pittsfield Cottages information

Number of reviews
Accommodation	121 Cottages
Lowest Price	CA $777
Highest Price	CA $777

Frequently asked questions

How much do cottages in Pittsfield cost?

You'll pay between CA $777 and CA $777 per night for cottages in Pittsfield. No matter your budget, an excellent stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Pittsfield with Expedia?

We think that a vacation should be a breeze, so if you're in search of cottages in Pittsfield at an affordable rate, Expedia has got your back. Save money and opt for a low-cost option far from the downtown buzz, or book an upmarket cottage to spoil your favorite people.

How can I find cheap cottages in Pittsfield?

Expedia is here to help you locate cheap cottages in Pittsfield. To reserve the perfect stay in just a few clicks, try out the filter tool to tailor your search results by budget, star rating and amenities.

What is there to do in Pittsfield near my cottage?

Whatever you're interested in, Pittsfield has plenty to keep you on the move. Hancock Shaker Village, Pittsfield State Forest and Arrowhead Museum are on most travelers' sightseeing plans. Don't head home without exploring Bousquet Ski Area, Barrington Stage Company and Berkshire Museum either. With Expedia's hotel deals in Pittsfield, you'll be able to discover more popular attractions like these with the cash you save.

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Dalton Vacation Rentals

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Check prices for these dates

Our top choices for Pittsfield cottages

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Beachwood Cottage

Berkshires farm, 30+ guests, 50 acres

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Berkshire Inn

Berkshires Untold

Best Western Plus Berkshire Hills Inn & Suites

Comfort Inn & Suites East Greenbush - Albany

The Yankee Inn

Berkshire Mountain Lodge

The Red Lion Inn

Vacation Village in the Berkshires

FairBridge Inn Express

Find out more about Pittsfield

Pittsfield Cottages information

Frequently asked questions

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Search Pittsfield Cottage Rentals from CA $777

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pittsfield cottages

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Beachwood Cottage

Berkshires farm, 30+ guests, 50 acres

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Berkshire Inn

Find out more about Pittsfield

Pittsfield Cottages information

Frequently asked questions

Explore a world of travel with Expedia