Windsor Hotel & Accommodation Deals 2026 from AU$103 - Compare prices by date

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Our top choices for Windsor hotels

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

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 spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

1. Hotel On North

Pittsfield

Devon

AU$214

includes taxes & fees

1 Nov - 2 Nov

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

A modern cafe with a counter, seating area, and large windows.

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.

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

Pittsfield

Ginger

AU$151

includes taxes & fees

19 Nov - 20 Nov

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.

A hotel room with a desk, computer, TV, and a chair.

3. FairBridge Inn Express

Pittsfield

Richard

AU$103

includes taxes & fees

4 Nov - 5 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 garden with a wooden house, a tree, and a person tending to plants.

A room with a hanging bed, a white wall, a window, and a door.

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.

4. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

AU$268

includes taxes & fees

21 Nov - 22 Nov

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

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

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

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

5. The Revival House

Adams

Katrina

AU$239

includes taxes & fees

2 Nov - 3 Nov

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

A garden with wooden Adirondack chairs and a stone pathway.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

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

6. Berkshire Mountain Lodge

Pittsfield

Joel

AU$170

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

A single-story building with a porch, a chimney, and a satellite dish.

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

7. Rodeway Inn

Adams

Joann

AU$107

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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.

8. The Yankee Inn

Lenox

Basil

AU$160

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a TV, a wooden dresser, and a desk.

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

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.

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

AU$190

includes taxes & fees

10 Nov - 11 Nov

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

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

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

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

10. The Central Downtown Inn & Suites

Pittsfield

Debra

AU$158

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

11. Berkshire Inn

Pittsfield

cheryl

AU$135

includes taxes & fees

21 Nov - 22 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

12. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

AU$155

includes taxes & fees

15 Nov - 16 Nov

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 featuring a table and chairs, a kitchenette with a coffee machine, and a television 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, a sofa, a coffee station, and a TV mounted on the wall.

13. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

AU$126

includes taxes & fees

25 Oct - 26 Oct

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 gazebo in a lush garden with flowering plants and a large tree.

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

14. Harbour House Inn

Cheshire

Gregory

AU$383

includes taxes & fees

28 Oct - 29 Oct

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

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

A wooden cabinet with a coffee maker and a white container.

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

15. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

AU$175

includes taxes & fees

31 Oct - 1 Nov

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

A spacious living room with large windows, a fireplace, and a variety of seating options.

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

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

16. Vacation Village in the Berkshires

Williamstown

Adrianne

AU$144

includes taxes & fees

2 Nov - 3 Nov

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

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

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 sofa, a coffee table, and a large window with a view of trees.

17. Berkshires Untold

Lenox

Madhavi R

AU$207

includes taxes & fees

1 Nov - 2 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".

18. The Springs Motel

New Ashford

Elizabeth

AU$165

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 large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

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

19. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

AU$204

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

20. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

AU$200

includes taxes & fees

1 Nov - 2 Nov

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Top Windsor Hotel Reviews

Recent Reviews in Windsor

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Very nice. Not five-star nice, but great lodging in a stunningly beautiful setting. This was my second stay, and it was great. Room was clean and bed was very comfortable. The staff are extremely helpful. Breakfast was a little stodgy (toaster didn’t work and the selection was pretty standard motel fare). I’ll definitely return just because of the location. Eating breakfast while watching a variety of waterfowl landing on the lake is extremely peaceful."

Vacation Village in the Berkshires

10/10 Excellent

"We had an amazing stay."

The Yankee Inn

8/10 Good

"Efficient & comfortable. Very good value."

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

The Williams Inn

10/10 Excellent

"Fantastic hotel! Would definitely stay again."

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent

"easy parking clean room staff very helpful they need to update their key card system...the cards easily become demagnetized and don't work. Staff very aware and quick to address problems"

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

More cheap accommodation in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

AU$103

4 Nov - 5 Nov

includes taxes & fees

5.4/10 (925 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

AU$126

25 Oct - 26 Oct

includes taxes & fees

7.6/10 Good! (929 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

AU$142

1 Nov - 2 Nov

includes taxes & fees

7.2/10 Good! (1,004 reviews)

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

1055 South Street Pittsfield MA

AU$151

19 Nov - 20 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

AU$160

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,011 reviews)

The Whitlock

16 Church St Lenox MA

AU$221

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (402 reviews)

Frequently asked questions

What is the best area to stay in Windsor?

The best area to stay in Windsor is the main town centre, particularly around the historic Market Square and along Peascod Street.This central area is the heart of Windsor, offering easy pedestrian access to many of the town's key attractions. You'll find a wide selection of shops, restaurants, and pubs here, all within a short stroll of Windsor Castle and the Long Walk. The streets are generally well-kept and easy to navigate.Couples looking for a romantic getaway will find the town centre ideal. With the castle on your doorstep, charming cobbled streets, and a variety of dining options from casual to fine dining, it provides a refined and convenient base for exploring. You can easily spend your days touring the castle, enjoying a boat trip on the River Thames, or simply relaxing in one of the many cafes.Families will also appreciate the convenience of staying in the town centre. Being close to the castle means less travel time with little ones, and there are several parks nearby, including Alexandra Gardens along the river, superb for children to play.

When is the best time to go to Windsor?

The best time to go to Windsor, Massachusetts, is during the summer months, from June to August, and the early autumn, specifically September and October.Summer offers warm, pleasant weather, ideal for outdoor activities like hiking, fishing, and exploring the natural beauty of the Berkshire Mountains. The days are long, allowing ample time for sightseeing and enjoying the region's lakes and rivers. This is a great time for families looking for a relaxed holiday with plenty of fresh air and nature.Early autumn brings cooler temperatures and the spectacular colours of the fall foliage. This period is particularly good for couples or solo travellers who appreciate scenic drives, photography, and outdoor adventures in a picturesque setting.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor.

How can I save on a hotel booking in Windsor with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Windsor hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Windsor?

Prices for hotels in Windsor often vary, but you can find a great deal from AU$103 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Explore a world of travel with Expedia

Book Hotels in Windsor on Expedia.com

Search Windsor hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Windsor hotels

1. Hotel On North

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

3. FairBridge Inn Express

4. The Trail in Adams - Berkshires’ Art Hotel

5. The Revival House

6. Berkshire Mountain Lodge

7. Rodeway Inn

8. The Yankee Inn

9. Hotel Downstreet, an Ascend Collection Hotel

10. The Central Downtown Inn & Suites

11. Berkshire Inn

12. Best Western Plus Berkshire Hills Inn & Suites

13. Howard Johnson by Wyndham Lenox

14. Harbour House Inn

15. Hampton Inn & Suites Berkshires-Lenox

16. Vacation Village in the Berkshires

17. Berkshires Untold

18. The Springs Motel

19. Hilton Garden Inn Lenox Pittsfield

20. Courtyard by Marriott Lenox Berkshires

Top Windsor Hotel Reviews

Recent Reviews in Windsor

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Vacation Village in the Berkshires

The Yankee Inn

Hotel On North

The Williams Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

FairBridge Inn Express

More cheap accommodation in Windsor

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Red Roof Inn PLUS+ South Deerfield – Amherst

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

The Yankee Inn

The Whitlock

Frequently asked questions

Explore a world of travel with Expedia

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