Windsor Cottages

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Windsor cottages

A wooden deck with a table, benches, and outdoor furniture.

1. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

Charlemont

includes taxes & fees

8 Nov - 9 Nov

A cabin with a wooden deck, a covered porch, and a gravel driveway.

2. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a balcony, a chimney, and a window with a view.

3. Berkshires farm, 30+ guests, 50 acres

New Lebanon

includes taxes & fees

18 Nov - 19 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

The Yankee Inn

10/10 Excellent

"We had a wonderful stay over the weekend. Bed VERY comfortable. Quiet, except one early am with kids running in the halls! Parents issue! Breakfast was good. Several items needing to be replenished each am. Had to go and ask the girls a few times. They were in the back room eating, seemingly unaware of restocking needed items. The bar on the weekend was an extra perk! Loved Carl 💕, the bartender , quite a conversationalist. Overall beautiful location , walking path in the back was nice, in the back of the hotel."

Quality Inn Lee - Lenox South

8/10 Good

"Bed was comfortable, breakfast was fine, and it's a generally attractive property. We were in room 125, which was awkwardly laid out. The toilet was mashed up against the sink, and the desk was opposite the foot of the bed, making a traffic bottleneck. I'd guess 126 is the same, but hopefully the rest of the rooms weren't."

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"Room was good. Location was great ! Close to South Deerfield center, close to Rte 116 and I-91. About equidistant from Amherst, Northampton and Greenfield. Electric car charger next door - level 3 in town center. Level 2 in Park and ride. Room clean and upkeep was by request not daily. Free coffee in room."

Find out more about Windsor