Hotels in Windsor, MA - Best Windsor Hotels from £50 - Fully Refundable Options

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Our top choices for Windsor hotels

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

A dining area with wooden tables and chairs, a television, and a door with a sign.

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

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

1. FairBridge Inn Express

Pittsfield

William

£50

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

2. Rodeway Inn

Adams

Joann

£57

includes taxes & fees

2 Nov - 3 Nov

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.

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

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

3. The Yankee Inn

Lenox

Basil

£90

includes taxes & fees

1 Nov - 2 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 modern cafe with a counter, seating area, and large windows.

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

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

Pittsfield

Ginger

£84

includes taxes & fees

11 Nov - 12 Nov

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

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

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.

5. The Revival House

Adams

Katrina

£127

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

6. Hotel On North

Pittsfield

Lawrence

£113

includes taxes & fees

3 Nov - 4 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 hotel room with two beds, a nightstand with a lamp, and a window with curtains.

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

7. The Central Downtown Inn & Suites

Pittsfield

Rena

£84

includes taxes & fees

15 Oct - 16 Oct

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

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

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

8. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

£67

includes taxes & fees

21 Oct - 22 Oct

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 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.

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

9. The Trail in Adams - Berkshires’ Art Hotel

Adams

Susan

£140

includes taxes & fees

12 Nov - 13 Nov

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

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

10. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

£108

includes taxes & fees

1 Nov - 2 Nov

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

A kitchen with a fireplace, dining area, and a large window with curtains.

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

11. Williamstown Motel

Williamstown

Ahmet

£63

includes taxes & fees

5 Nov - 6 Nov

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

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

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

A garden with wooden Adirondack chairs and a stone pathway.

12. Berkshire Mountain Lodge

Pittsfield

Kathleen

£89

includes taxes & fees

9 Nov - 10 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

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

13. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

£79

includes taxes & fees

3 Nov - 4 Nov

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

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

£93

includes taxes & fees

10 Nov - 11 Nov

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

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

A modern hotel building with the name "Hotel Downtown" on the facade.

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

15. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

£101

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

16. Berkshire Inn

Pittsfield

Linda

£70

includes taxes & fees

13 Nov - 14 Nov

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

A conference room with a whiteboard, tables, and chairs.

An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

17. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

£87

includes taxes & fees

13 Nov - 14 Nov

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

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.

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.

18. Harbour House Inn

Cheshire

Gregory

£203

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.

19. Berkshires Untold

Lenox

Madhavi R

£110

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

20. The Springs Motel

New Ashford

Elizabeth

£88

includes taxes & fees

1 Nov - 2 Nov

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Top Windsor Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"The rooms were clean and parking what’s convenient."

Vacation Village in the Berkshires

10/10 Excellent

"Amazing pool and great full kitchens in rooms."

Hotel On North

10/10 Excellent

"This is a great hotel.. likely the best place to stay in Pittsfield. Just an overnight stop so not time to get a good read on the area but a good option for the Berkshires if you you don't want to pay the Lenox/Stockbridge premium."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"O"

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

Berkshire Mountain Lodge

10/10 Excellent

"The room was fantastic. Great place to stay in the Berkshires. The hot tub wasn't working, but things happen. Other than that, it was a perfect stay."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

The Red Lion Inn

8/10 Good

"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good

"no breakfast"

More cheap stays in Windsor

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

£50

26 Oct - 27 Oct

includes taxes & fees

5.4/10 (923 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

£67

21 Oct - 22 Oct

includes taxes & fees

7.6/10 Good! (923 reviews)

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

£75

1 Nov - 2 Nov

includes taxes & fees

7.2/10 Good! (1,008 reviews)

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

1055 South Street Pittsfield MA

£84

11 Nov - 12 Nov

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

£90

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

The Whitlock

16 Church St Lenox MA

£108

1 Nov - 2 Nov

includes taxes & fees

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 canceled 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 much is the nightly rate at a Windsor hotel?

Prices for hotels in Windsor often vary, but you can find a great deal from £50 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 the cheapest rate.

Explore a world of travel with Expedia

Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, MA from £50

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

1. FairBridge Inn Express

2. Rodeway Inn

3. The Yankee Inn

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

5. The Revival House

6. Hotel On North

7. The Central Downtown Inn & Suites

8. Howard Johnson by Wyndham Lenox

9. The Trail in Adams - Berkshires’ Art Hotel

10. Hilton Garden Inn Lenox Pittsfield

11. Williamstown Motel

12. Berkshire Mountain Lodge

13. Best Western Plus Berkshire Hills Inn & Suites

14. Hampton Inn & Suites Berkshires-Lenox

15. Hotel Downstreet, an Ascend Collection Hotel

16. Berkshire Inn

17. Holiday Inn & Suites Pittsfield-Berkshires by IHG

18. Harbour House Inn

19. Berkshires Untold

20. The Springs Motel

Top Windsor Hotel Reviews

Quality Inn Lee - Lenox South

Vacation Village in the Berkshires

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Berkshire Mountain Lodge

The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

More cheap stays 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

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