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Aug 28 - Aug 29
Tomorrow
Aug 29 - Aug 30
This weekend
Aug 28 - Aug 30
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Sep 4 - Sep 6

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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 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.

1. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
ERICIA
CA $76
CA $85 total
includes taxes & fees
Sep 29 - Sep 30
FairBridge Inn Express
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.

2. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
CA $177
CA $198 total
includes taxes & fees
Sep 16 - Sep 17
The Yankee Inn
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 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.

3. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Jermaine
CA $159
CA $178 total
includes taxes & fees
Sep 20 - Sep 21
Best Western Plus Berkshire Hills Inn & Suites
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A multi-story hotel with a brick facade and a flat roof.
A pool area with a glass ceiling, multiple levels, and outdoor seating.
A lobby with three grey armchairs, a small round table with a plant, and a patterned rug.

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Myrna
CA $163
CA $183 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 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.

5. Rodeway Inn

Rodeway Inn
Adams
United States
Andrew
CA $100
CA $111 total
includes taxes & fees
Sep 6 - Sep 7
Rodeway Inn
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 bedroom with a bed, a sofa, a fireplace, and a chandelier.

6. The Revival House

The Revival House
Adams
United States
James
CA $211
CA $236 total
includes taxes & fees
Sep 6 - Sep 7
The Revival House
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.

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Sheila
CA $108
CA $121 total
includes taxes & fees
Sep 24 - Sep 25
Howard Johnson by Wyndham Lenox
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 residential street with a paved road, a lamp post, and flowering trees.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

8. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Adriana
CA $119
CA $133 total
includes taxes & fees
Sep 27 - Sep 28
Berkshire Inn
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern hotel building with the name "Hotel Downtown" on the facade.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A modern interior with a large window, a wooden table, and bar stools.

9. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Peter
CA $211
CA $235 total
includes taxes & fees
Sep 20 - Sep 21
Hotel Downstreet, an Ascend Collection Hotel
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 seating areas, a coffee station, and large windows offering a view of greenery.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ken
CA $163
CA $183 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.

11. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
CA $131
CA $177 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

12. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
CA $169
CA $189 total
includes taxes & fees
Sep 9 - Sep 10
Hampton Inn & Suites Berkshires-Lenox
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.

13. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
CA $137
CA $153 total
includes taxes & fees
Aug 30 - Aug 31
The Central Downtown Inn & Suites
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.

14. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $170
CA $186 total
includes taxes & fees
Aug 31 - Sep 1
The Springs Motel
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.
A spacious living room with large windows, a fireplace, and a variety of seating options.

15. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Alex
CA $120
CA $150 total
includes taxes & fees
Aug 31 - Sep 1
Vacation Village in the Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
CA $152
CA $170 total
includes taxes & fees
Sep 20 - Sep 21
Quality Inn Lee - Lenox South
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 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.

17. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
CA $314
CA $332 total
includes taxes & fees
Sep 24 - Sep 25
Harbour House Inn
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A white two-story building with a porch, labeled as a motel.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A hay bale display with pumpkins and scarecrows.

18. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Richard
CA $117
CA $131 total
includes taxes & fees
Aug 30 - Aug 31
Willows Motel Williamstown
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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.

19. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
CA $212
CA $236 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Lenox Pittsfield
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 hallway with a wooden door, a bench, and a staircase.

20. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
Adams
United States
Jenna
CA $274
CA $306 total
includes taxes & fees
Aug 31 - Sep 1
The Trail in Adams - Berkshires’ Art Hotel
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Top Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted less than an hour ago
The Red Lion Inn
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"It is a safe place with friendly staff and clean accommodations; it is an excellent spot for traveling with children."
Jiye 2-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Room was"
Christopher 1-night trip
Posted 5 hours ago
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Chic bar and outdoor space. Nice remodel."
Kurt 1-night trip
Posted 6 hours ago
Berkshires Untold
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Friendly staff and clean comfortable room! Location is super"
Kathleen 1-night trip
Posted 21 hours ago
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
Corinne 1-night trip
Posted 23 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
JAMES 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 1 day ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Nice place"
Peter 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
CA $84
per night
Sep 10 - Sep 11
FairBridge Inn Express
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
CA $108
per night
Sep 24 - Sep 25
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 $137
per night
Sep 7 - Sep 8
Red Roof Inn PLUS+ South Deerfield – Amherst
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
CA $159
per night
Sep 20 - Sep 21
8.6/10 Excellent! (1,000 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
CA $163
per night
Sep 8 - Sep 9
9.4/10 Exceptional! (176 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
CA $177
per night
Sep 16 - Sep 17
9.2/10 Wonderful! (1,001 reviews)
The Yankee Inn

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 $94 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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