Pittsfield Vacation Homes

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Our top choices for Pittsfield holiday homes

Hancock Village Inn Near Jiminy Peak

Hancock

Stephanie B.

HK$8,481 total

includes taxes & fees

9 Jun - 10 Jun

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

Pittsfield

Liz V.

HK$4,324 total

includes taxes & fees

10 Jun - 11 Jun

Home in Great Barrington

Great Barrington

Jessica S.

HK$2,857 total

includes taxes & fees

14 Jun - 15 Jun

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

Hancock

Christy F.

HK$4,137 total

includes taxes & fees

8 Jun - 9 Jun

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

Sherwood Forest

Sharon K.

HK$3,343 total

includes taxes & fees

23 Jun - 24 Jun

Cozy Riverside Berkshires Retreat

Great Barrington

Cristine C.

HK$2,497 total

includes taxes & fees

17 Jun - 18 Jun

Near Tanglewood: Historic Summer Retreat

New Lebanon

Karen H.

HK$3,009 total

includes taxes & fees

7 Jun - 8 Jun

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

Sherwood Forest

Frank M.

HK$3,047 total

includes taxes & fees

7 Jun - 8 Jun

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

Corinne T.

HK$3,143 total

includes taxes & fees

8 Jun - 9 Jun

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Roberta

HK$10,406 total

includes taxes & fees

13 Jun - 14 Jun

Treetop Hideaway in Tyringham

Monterey

Sarah B.

HK$4,587 total

includes taxes & fees

9 Jun - 10 Jun

North Getaway Cottage

Williamstown

Carole S.

HK$3,514 total

includes taxes & fees

9 Jun - 10 Jun

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

West Sand Lake

LauraS

HK$4,337 total

includes taxes & fees

2 Jul - 3 Jul

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

SteveS

HK$3,876 total

includes taxes & fees

10 Jun - 11 Jun

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

Lauren C.

HK$4,424 total

includes taxes & fees

15 Jun - 16 Jun

The Greylock Cabin

Florida

Ron L.

HK$3,443 total

includes taxes & fees

10 Jun - 11 Jun

Perfect Nature Haven In Great Barrington

Great Barrington

Ethel B.

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

HK$2,640 total

includes taxes & fees

17 Jun - 18 Jun

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Marianne B.

HK$3,970 total

includes taxes & fees

12 Jun - 13 Jun

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

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Top Pittsfield Hotel Reviews

Hilton Garden Inn Lenox Pittsfield

10/10 Excellent

"Five Star stay!"

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Hi, for the most part, my stay was fantastic. The staff were excellent. Breakfast was awesome! The Restaurant and Bar were great! My one negative comment is about the lack of hot water in the morning for me to take a shower. Very disappointing. I am coming back there the next 2 weeks and I hope that the Hot Water situation will be rectified."

Berkshires Untold

8/10 Good

"Here’s what we liked: If we were just reviewing BERKSHIRES UNTOLD based on the staff, we’d be giving it a 5. The staff were extremely friendly, helpful and gracious. When we asked for extra towels and requested a room change, they accommodated those requests immediately. After we switched rooms they checked to see if we were happier. This is exactly the kind of service you want in a hotel or inn. Other good things - The bed was comfortable and there was enough counter space in the bathroom and at the desk area. We also liked that there was a breakfast seating area, bar and small indoor seating area plus outdoor seating with gas fire pits. So, why are we giving the place a 3 overall? It really needed more attention to detail. The carpet in our original room was not in good shape and the fitted bed sheet had a small rip on my side. Some of the room furniture was dinged up and a sofa in the common seating area had some shredded fabric. One thing we didn’t like (that they couldn’t exactly help) was that we were there on a late spring wedding weekend, so there were buses idling in front of our room with loud talkers and smokers nearby. It felt like they were in our room along with the smoke and fumes. The trend of turning motels into better motels is interesting. They’re less expensive and are sometimes more original. But you’re still in a motel. If you value soundproofing and consistently better quality, a mid range chain may be a better choice."

Berkshire Mountain Lodge

10/10 Excellent

"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope the hinge was repaired before the next guest checked in. 2) The toilet flush handle was slightly cracked but still functional. We forgot to notify the staff; it was barely noticeable. 3) The guest or owner in the room above our room walked very loudly. We were used to hearing noises from people walking in the hall but this was our first time hearing footsteps through the ceiling. Other than those three items, our stay was excellent. The front desk staff were courteous and helpful. The housekeeping crew were unobtrusive. The long driveway to the ample parking lot gives enough distance from the busy"

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