Hotels in Windsor

City, hotel name, or address

Dates

Travellers

I'm travelling for business

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay in Windsor?

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Windsor on Hotels.com. These Windsor hotels consistently deliver on quality, location and traveller experience. Last updated on 19 October 2026.

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

1. The Yankee Inn

Lenox

AU$148

includes taxes & fees

27 Oct - 28 Oct

A living room with a fireplace, two sofas, and four black side tables.

A dining area with a wooden table, four chairs, and a framed picture on the wall.

A two-story building with a symmetrical facade, large columns, and a central entrance.

A doorway leading to a room with a fireplace, a sofa, and decorative wall sconces.

2. The Revival House

Adams

AU$222

includes taxes & fees

5 Nov - 6 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A snack bar with shelves of snacks and a refrigerated display.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

AU$153

includes taxes & fees

17 Nov - 18 Nov

A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

A hallway with a wooden door, a bench, and a staircase.

A modern living room with a sofa, armchair, coffee table, and ottoman. There is a large abstract painting on the wall, a dining table with chairs, and a staircase leading to an upper level.

A garden with a wooden house, a tree, and a person tending to plants.

4. The Trail in Adams - Berkshires’ Art Hotel

Adams

AU$277

includes taxes & fees

19 Nov - 20 Nov

A building entrance with a large planter with purple flowers and a small tree.

A library with bookshelves, a television, and two armchairs.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

5. Hotel On North

Pittsfield

AU$201

includes taxes & fees

19 Nov - 20 Nov

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern interior with a large window, a wooden table, and bar stools.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

6. Hotel Downstreet, an Ascend Collection Hotel

North Adams

AU$192

includes taxes & fees

8 Nov - 9 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

7. Berkshire Mountain Lodge

Pittsfield

AU$171

includes taxes & fees

10 Nov - 11 Nov

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

A gazebo in a garden with a house in the background.

A spacious living room with a large window, a sofa, a chair, and a dining area.

A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.

8. Harbour House Inn

Cheshire

AU$386

includes taxes & fees

22 Oct - 23 Oct

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

9. Howard Johnson by Wyndham Lenox

Lenox

AU$127

includes taxes & fees

20 Oct - 21 Oct

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

A cozy library with bookshelves, a fireplace, and comfortable seating.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

10. Berkshires Untold

Lenox

AU$209

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

11. Hampton Inn & Suites Berkshires-Lenox

Lenox

AU$176

includes taxes & fees

1 Nov - 2 Nov

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A sauna room with wooden walls, a bench, a heater, and a door leading to an outdoor area.

12. Blue Vista Motor Lodge

North Adams

AU$246

includes taxes & fees

19 Nov - 20 Nov

A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

A reception desk with a computer, a monitor, and a sign about Choice Privileges.

A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.

A hotel room with a desk, chair, TV, and a painting on the wall.

13. Rodeway Inn

Adams

AU$108

includes taxes & fees

3 Nov - 4 Nov

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

A residential street with a paved road, a lamp post, and flowering trees.

14. Berkshire Inn

Pittsfield

AU$137

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

An outdoor seating area with Adirondack chairs and a fire feature.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

15. Element by Marriott Lenox Berkshires

Lenox

AU$217

includes taxes & fees

8 Nov - 9 Nov

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

16. Vacation Village in the Berkshires

Williamstown

AU$145

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating and a fire pit.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

A spacious living room with a large sofa, a coffee table, and a fireplace.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

17. Hilton Garden Inn Lenox Pittsfield

Pittsfield

AU$206

includes taxes & fees

1 Nov - 2 Nov

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

A hallway with a collection of plates on the walls, leading to a staircase.

18. The Porches Inn at Mass MoCA

North Adams

AU$277

includes taxes & fees

19 Nov - 20 Nov

A patio area with outdoor furniture, a fire pit, and potted plants.

A cozy living room with a stone fireplace, comfortable seating, and a television.

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

19. The Springs Motel

New Ashford

AU$167

includes taxes & fees

1 Nov - 2 Nov

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A compact living space with a kitchenette, a dining area, and a sofa.

A modern apartment with a living room, kitchenette, and dining area.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

20. The Central Downtown Inn & Suites

Pittsfield

AU$159

includes taxes & fees

20 Oct - 21 Oct

View all properties

Go beyond your typical stay in Windsor

Check out reviews of Windsor hotels guests love

The Yankee Inn

Lenox

10/10 Exceptional

Lawrence

Hampton Inn & Suites Berkshires-Lenox

Lenox

10/10 Exceptional

Anonymous traveller

A garden with a swing set, a blue chair, and a flower bed.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A swimming pool with lounge chairs and a fence.

Maple Terrace Motel

Williamstown

10/10 Exceptional

Karen

Frequently Asked Questions

How much does a hotel room cost in Windsor?

You can discover great hotels in Windsor from AU$107 with properties to suit all budgets and needs. If you're after an affordable hotel in Windsor that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Windsor hotels?

Discover great deals on Windsor hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Windsor hotels.

Can I book Windsor hotels with free cancellation?

To book a refundable Windsor hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

Keep exploring

Lodging