Default HTG hotel image

Find hotels in Windsor, MA from CA $98

  • 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

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A hotel room with a desk, computer, TV, and a chair.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.
A dining area with wooden tables and chairs, a television, and a door with a sign.

1. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
William
CA $88
CA $98 total
includes taxes & fees
Oct 20 - Oct 21
FairBridge Inn Express
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Susan
CA $141
CA $157 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

3. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $139
CA $156 total
includes taxes & fees
Oct 19 - Oct 20
The Yankee Inn
A building entrance with a large planter with purple flowers and a small tree.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A library with bookshelves, a television, and two armchairs.

4. Hotel On North

Hotel On North
Pittsfield
United States
Drew
CA $159
CA $178 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Jay
CA $112
CA $157 total
includes taxes & fees
Oct 19 - Oct 20
Berkshire Mountain Lodge
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 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.

6. The Revival House

The Revival House
Adams
United States
Katrina
CA $223
CA $249 total
includes taxes & fees
Nov 1 - Nov 2
The Revival House
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 residential street with a paved road, a lamp post, and flowering trees.
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

7. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Kristina
CA $114
CA $127 total
includes taxes & fees
Nov 1 - Nov 2
Berkshire Inn
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 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.

8. Rodeway Inn

Rodeway Inn
Adams
United States
Brandie
CA $101
CA $113 total
includes taxes & fees
Nov 1 - Nov 2
Rodeway Inn
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.
Indoor pool

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Jacob
CA $123
CA $153 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
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.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

10. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
CA $141
CA $157 total
includes taxes & fees
Oct 20 - Oct 21
The Central Downtown Inn & Suites
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Pool
Exterior
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

11. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
CA $173
CA $193 total
includes taxes & fees
Oct 20 - Oct 21
Hampton Inn & Suites Berkshires-Lenox
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 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 hallway with a wooden door, a bench, and a staircase.
A room with a hanging bed, a white wall, a window, and a door.

12. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
Adams
United States
Susan
CA $230
CA $257 total
includes taxes & fees
Nov 1 - Nov 2
The Trail in Adams - Berkshires’ Art Hotel
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

13. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Joe
CA $133
CA $148 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
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 bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A poolside area with lounge chairs, umbrellas, and a swimming pool.

14. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $162
CA $177 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
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.

15. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Alexandra
CA $170
CA $190 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Downstreet, an Ascend Collection Hotel
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 hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

16. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
COLLEEN
CA $112
CA $125 total
includes taxes & fees
Oct 12 - Oct 13
Howard Johnson by Wyndham Lenox
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

17. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
CA $182
CA $203 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 garden with a house in the background.
A gazebo in a lush garden with flowering plants and a large tree.

18. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
CA $360
CA $381 total
includes taxes & fees
Oct 26 - Oct 27
Harbour House Inn
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

Berkshires Untold
Lenox
United States
Madhavi R
CA $187
CA $209 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
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.

20. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
CA $179
CA $200 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Clean, big rooms!"
Mark 1-night trip
Posted 7 hours ago
Howard Johnson by Wyndham Lenox
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Awesome!"
soren 1-night trip
Posted 8 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel On North

Hotel On North

10/10 Excellent
"Great place!"
Lawrence 1-night trip
Posted 10 hours ago
Hotel On North
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 13 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Berkshires Untold

Berkshires Untold

8/10 Good
"All was good for the price. Great location. Gentlemen at the bar and check-in was very pleasant and helpful. Dinner could have been better prepared."
Dan 1-night trip
Posted 14 hours ago
Berkshires Untold
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Most helpful staff, very clean and best breakfast around"
Sheldon 2-night trip
Posted 14 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very unique property. Great nostalgic atmosphere."
TAKOSHIA 1-night trip
Posted 15 hours ago
The Red Lion Inn
The Williams Inn

The Williams Inn

10/10 Excellent
"Great"
William 1-night trip
Posted 2 days ago
The Williams Inn
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
CA $88
CA $98 total
Oct 20 - Oct 21
includes taxes & fees
5.4/10 (911 reviews)
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
CA $112
CA $125 total
Oct 12 - Oct 13
includes taxes & fees
7.6/10 Good! (918 reviews)
Howard Johnson by Wyndham Lenox
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA
CA $127
CA $142 total
Nov 1 - Nov 2
includes taxes & fees
Red Roof Inn PLUS+ South Deerfield – Amherst
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
CA $139
CA $156 total
Oct 19 - Oct 20
includes taxes & fees
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
CA $141
CA $157 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (221 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Whitlock

The Whitlock

16 Church St Lenox MA
CA $212
CA $237 total
Oct 28 - Oct 29
includes taxes & fees
The Whitlock

Hotels in Windsor with star rating

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 CA $98 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