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Oct 13 - Oct 14
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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 hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
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

FairBridge Inn Express
Pittsfield
United States
William
CA $79
CA $88 total
includes taxes & fees
Nov 5 - Nov 6
FairBridge Inn Express
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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

2. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $136
CA $152 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A building entrance with a large planter with purple flowers and a small tree.
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.
A library with bookshelves, a television, and two armchairs.

3. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
CA $191
CA $214 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A snack bar with shelves of snacks and a refrigerated display.
A modern cafe with a counter, seating area, and large windows.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ginger
CA $141
CA $158 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 doorway leading to a room with a fireplace, a sofa, and decorative wall sconces.
A dining area with a wooden table, four chairs, and a framed picture on the wall.

5. The Revival House

The Revival House
Adams
United States
Katrina
CA $214
CA $239 total
includes taxes & fees
Nov 2 - Nov 3
The Revival House
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.
A single-story building with a porch, a chimney, and a satellite dish.
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.

6. Rodeway Inn

Rodeway Inn
Adams
United States
Joann
CA $96
CA $107 total
includes taxes & fees
Nov 2 - Nov 3
Rodeway Inn
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 garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Kathleen
CA $121
CA $168 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
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 hotel building with the name "Hotel Downtown" on the facade.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.

8. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
Canada
Tara
CA $170
CA $190 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Downstreet, an Ascend Collection Hotel
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.

9. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Linda
CA $114
CA $127 total
includes taxes & fees
Nov 12 - Nov 13
Berkshire Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
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.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

10. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
CA $141
CA $158 total
includes taxes & fees
Oct 20 - Oct 21
The Central Downtown Inn & Suites
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 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.

11. 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 12 - Nov 13
The Trail in Adams - Berkshires’ Art Hotel
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

12. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Mark
CA $147
CA $164 total
includes taxes & fees
Nov 13 - Nov 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 a coffee machine, a water dispenser, and a sign indicating the fitness center.
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 grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

13. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
James
CA $133
CA $149 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.
A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
CA $156
CA $175 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Berkshires-Lenox
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.
Indoor pool
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.

15. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Pofen
CA $115
CA $144 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
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 hotel room with a large bed, a desk, a chair, and a view of the outdoors.

16. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $151
CA $165 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
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 featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

17. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Aleksandr
CA $113
CA $126 total
includes taxes & fees
Oct 20 - Oct 21
Howard Johnson by Wyndham Lenox
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.
Exterior

18. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
CA $182
CA $204 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 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.
A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.

19. Williamstown Motel

Williamstown Motel
Williamstown
United States
Ahmet
CA $103
CA $115 total
includes taxes & fees
Nov 8 - Nov 9
Williamstown Motel
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 cozy library with bookshelves, a fireplace, and comfortable seating.
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.

20. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
CA $186
CA $207 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Amazing pool and great full kitchens in rooms."
robin 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Hotel On North

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."
John 1-night trip
Posted 5 hours ago
Hotel On North
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"O"
Ilya 2-night trip
Posted 5 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

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"
Mark 1-night trip
Posted 5 hours ago
The Yankee Inn
Berkshire Mountain Lodge

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."
Christian 2-night trip
Posted 8 hours ago
Berkshire Mountain Lodge
The Cornell Inn, Lenox & The Berkshires

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."
Alexandra 1-night trip
Posted 12 hours ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

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."
Patricia 1-night trip
Posted 12 hours ago
The Red Lion Inn
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good
"no breakfast"
Jason 4-night trip
Posted 20 hours ago
Red Roof Inn PLUS+ South Deerfield – Amherst
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"It was good"
Vishva 1-night trip
Posted 1 day ago
Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
CA $79
CA $88 total
Nov 5 - Nov 6
includes taxes & fees
5.4/10 (923 reviews)
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
CA $113
CA $126 total
Oct 20 - Oct 21
includes taxes & fees
7.6/10 Good! (923 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
7.2/10 Good! (1,008 reviews)
Red Roof Inn PLUS+ South Deerfield – Amherst
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
CA $136
CA $152 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
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 $158 total
Nov 10 - Nov 11
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Whitlock

The Whitlock

16 Church St Lenox MA
CA $208
CA $233 total
Nov 2 - Nov 3
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 $88 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.

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