Monterey Vacation Homes

A lake surrounded by autumn-colored trees reflecting on the water.

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Our top choices for Monterey holiday homes

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

New Lebanon

HK$6,220 total

includes taxes & fees

13 Aug - 14 Aug

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$5,411 total

includes taxes & fees

22 Jul - 23 Jul

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Mark Cristen J.

HK$8,591 total

includes taxes & fees

21 Jul - 22 Jul

Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

HK$2,811 total

includes taxes & fees

10 Aug - 11 Aug

Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Great Barrington

Julie J.

HK$3,485 total

includes taxes & fees

9 Aug - 10 Aug

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

Great Barrington

Roberta

HK$10,413 total

includes taxes & fees

23 Jul - 24 Jul

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

HK$3,985 total

includes taxes & fees

2 Aug - 3 Aug

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

Sherwood Forest

Frank M.

HK$3,403 total

includes taxes & fees

28 Jul - 29 Jul

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Top Monterey Hotel Reviews

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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