City Meadow Boardwalk Holiday Houses

A wooden boardwalk leading to a beach with a bird on the railing.

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Our top choices for City Meadow Boardwalk holiday homes

A wooden cabin interior with a bench, a rug, and a hanging plant.

1. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

Thomas C.

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a nightstand, a lamp, a window with curtains, a television, and a bathroom door.

2. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

includes taxes & fees

7 Oct - 8 Oct

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

3. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

12 Oct - 13 Oct

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

4. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

26 Oct - 27 Oct

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

5. 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

28 Oct - 29 Oct