Monterey Holiday Homes from €198: Search Top House Rentals

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

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Our top choices for Monterey holiday homes

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

includes taxes & fees

13 Sept - 14 Sept

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

includes taxes & fees

7 Sept - 8 Sept

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

3. 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.

includes taxes & fees

6 Oct - 7 Oct

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

includes taxes & fees

9 Sept - 10 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

8 Sept - 9 Sept

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

6. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

includes taxes & fees

8 Sept - 9 Sept

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

7. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

includes taxes & fees

9 Sept - 10 Sept

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

includes taxes & fees

15 Sept - 16 Sept

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Top Monterey Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Great location and beautiful views overlooking the lake. A super quick drive to Main Street in Lee or over to Lenox! We didn’t have time to eat at the restaurant but the food looks amazing!"

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay

8/10 Good

"The house & location are wonderful. We were there for a week & we totally enjoyed ourselves. The difference between a good house & an excellent house is that everything works in an excellent house. There are a few items that do need attention. (1) The lock on the back door to the patio was broken when we arrived. We were all surprised it was not fixed before our arrival. I reported it the first day but it never was fixed. A temporary solution was offered the day before we left. (2) The water pressure is poor. A plumber was sent out the first day to try to fix it. An air lock was the problem and venting that was only a temporary solution. We were a total of 6 adults & only one person could take a shower at a time. If two people showered, one shower would just trickle. If the sink in the kitchen was on at the same time, one of the showers would stop for a minute. An air lock in the pipes would ensue. For a house that is supposed to sleep 10, that is just not acceptable. (3) Hot water. The last person to shower never had enough. (4) No dressers. 3 couples with clothes for a week. The limited shelving in the closets were not enough. (5) No full length mirrors. (6) The internet kicks you off randomly. (7) The pool table would be great if there weren’t an obvious slant that gathered the balls on one side of the table. The surface of the table has a tear & there was no chalk for the cue sticks. (8) The dock has no cleats. There are poles at each end of the dock that be used."

Find out more about Monterey

Monterey Holiday Homes information

Number of reviews	324
Accommodation	372 Holiday Homes
Lowest Price	€198
Highest Price	€1,062

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Our top choices for Monterey holiday homes

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