The Berkshires Vacation Homes

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Our top choices for The Berkshires holiday homes

Home in Great Barrington

Great Barrington

Jessica S.

HK$2,803 total

includes taxes & fees

1 Jun - 2 Jun

Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

HK$2,610 total

includes taxes & fees

9 Jun - 10 Jun

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

Sherwood Forest

Frank M.

HK$3,091 total

includes taxes & fees

1 Jun - 2 Jun

Cozy cottage in the Berkshires

PITTSFIELD

HK$2,835 total

includes taxes & fees

29 May - 30 May

Cozy Riverside Berkshires Retreat

Great Barrington

Jennifer L.

HK$2,481 total

includes taxes & fees

27 May - 28 May

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

Sherwood Forest

Sharon K.

HK$2,912 total

includes taxes & fees

27 May - 28 May

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Javier

HK$4,241 total

includes taxes & fees

27 May - 28 May

The Greylock Cabin

Florida

Ron L.

HK$3,206 total

includes taxes & fees

27 May - 28 May

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Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Terrific generous breakfadt menu, cozy eating lounge. The room was in tip top shape and the hotel is superbly located right on Main Street and in walking proximity of shops, stores restaurants and cafes. Ideal place to stay abd reasonably priced room rates."

Vacation Village in the Berkshires

8/10 Good

"Very clean rooms. The staff was great at checking in; we had never been here, so we got the whole run down! They even show movies twice a day in their theater! They have a great indoor pool and game room, plus a great lobby to sit and relax. Cozy room to watch the rain, play games and eat snacks! For the most part, very quiet, clean, spacious for 2 people on a long weekend getaway! They had all the dishes, pots, pans to cook a nice meal, even had a wine bottle opener! Only downside was the weather, you could not go walking around or sit on the open porch, too much rain! Highly recommended for a couple or the entire family, a really great place to enjoy the Berkshires!"

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Great location close to everything. The staff was very helpful. The breakfast was perfect in every way. The room was also perfect… nice little kitchen… No dishes or silverware but I sink and refrigerator microwave , coffee pot so just enough. Really comfortable bed!"

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"The rooms are not at all fancy, but perfect for a family if you want to get away for a few nights. We went with my 3, 4, and 7-year-olds and spent two nights playing in the pool, mini-golfing, and hitting the arcade once or twice. Again, not very high-end, but if you’re with children who love a pool and easy activities, it’s a good choice."

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