Sandisfield Vacation Homes

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Our top choices for Sandisfield holiday homes

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

Sherwood Forest

William C B.

HK$2,287 total

includes taxes & fees

20 Sept - 21 Sept

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

Sherwood Forest

Sharon K.

HK$2,942 total

includes taxes & fees

29 Sept - 30 Sept

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

Sherwood Forest

Frank M.

HK$3,086 total

includes taxes & fees

28 Sept - 29 Sept

4. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

HK$4,527 total

includes taxes & fees

21 Sept - 22 Sept

5. Home in Great Barrington

Great Barrington

HEATHER G.

HK$2,711 total

includes taxes & fees

21 Sept - 22 Sept

6. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

HK$3,455 total

includes taxes & fees

12 Oct - 13 Oct

7. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

HK$2,761 total

includes taxes & fees

22 Sept - 23 Sept

8. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

HK$2,484 total

includes taxes & fees

20 Sept - 21 Sept

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Top Sandisfield Hotel Reviews

Berkshires Untold

10/10 Excellent

"Liked everything! Mostly, the people. The staff was friendly and excited to serve us"

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"I really love staying here. It’s no nonsense clean and i feel safe traveling as a woman alone… However they really need to step up their morning breakfast. I eat gluten free and they never have any. I’ve asked for ivermectin a month now and they just tell me they will mention it…."

Quality Inn Westfield - Springfield

8/10 Good

"Really easy to find, right off the highway. All staff were very helpful. The complimentary breakfast was impressive for the amount we paid for the room. It was an assortment of muffins/ bagels/toast and your typical continental breakfast stuff with additional microwave-heated eggs/ sausage and a self serve Belgian waffle maker. Breakfast area was clean and well looked after. As far as the room, it was fine. Beds were comfortable, shower hot, good pressure. 👎The light over the fridge was burnt out, visible crud built up under shower faucet and shampoo dispenser, hair dryer had someone's makeup stuck to it, ironing board was broken and stained. All in all, pretty good for $160/ night."

Simsbury 1820 House

10/10 Excellent

"We had a lovely room on the second floor. Staff was friendly and helpful. Some friends stayed in a third floor room and were not happy with the room. The ceiling was low. There was a roof line over the bed and they kept knocking their heads. We also noted a 400 series of rooms that were on the other side of the parking lot from the inn. The building looked newer, Don’t know what the rooms there are like. We were in room 201."

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