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23 Oct - 24 Oct
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24 Oct - 25 Oct
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24 Oct - 26 Oct
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31 Oct - 2 Nov

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Top hotels and accommodation in Windsor

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.2 out of 10, Wonderful, (1002)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is AU$183
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (773)
"Great hotel with a beautiful restaurant and bar. They have a wonderful patio with couches and fire pits. Great place to spend time hanging out."
United States
Rebecca
The price is AU$159
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1017)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
United States
Susan M
The price is AU$218
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (916)
"Enjoyable stay. Staff were very nice. "
United States
Claire
The price is AU$177
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2096)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
The price is AU$280
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1001)
"Staff was very welcoming and friendly! They provided great tips on restaurants and things to do in are."
United States
Robert
The price is AU$241
includes taxes & fees
9 Nov - 10 Nov
Hotel Downstreet, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (723)
"Room was very spacious with separate bedroom and full kitchen. Pool/hot tub area was great. Conveniently located to local attractions and restaurants."
United States
Gerard
The price is AU$195
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is AU$247
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (765)
"Lovely spot, great accommodations, friendly staff, and great location."
United States
Joanne
The price is AU$243
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (784)
"Nice hotel. Very friendly and professional staff. "
United States
Magen
The price is AU$180
includes taxes & fees
11 Nov - 12 Nov
Hotel On North
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1016)
"If you're looking for a classic New England Inn the Red Lion fits the bill. Beautiful porch to enjoy cocktails and coffee. Rustic Inn and dining room as restaurant options. Stockbridge offers other great dining options and shopping. "
United States
Bill
The price is AU$310
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (799)
"Good service and people"
United States
Jerod
The price is AU$116
includes taxes & fees
9 Nov - 10 Nov
FairBridge Inn Express
Front of property – evening/night
The Williams Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (528)
"Beautiful hotel with amazing service, nice rooms and a great bar/restaurant right on the property. Very convenient for a business trip!"
United States
Nancy
The price is AU$339
includes taxes & fees
17 Nov - 18 Nov
The Williams Inn
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (555)
"Very quiet and comfortable "
United States
Beth
The price is AU$220
includes taxes & fees
10 Nov - 11 Nov
The Constance by the Lenox Collection
Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
7.2 out of 10, Good, (1038)
"Great location"
United States
Linda
The price is AU$161
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn PLUS+ South Deerfield – Amherst
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (330)
"My five star rating is based on the rental being an exceptional value at the rate I paid (the rate I found on Expedia). Our suite was a plain but super comfortable one bedroom apartment with full kitchen and living area, plenty of storage space. The location is extremely convenient, and it was very clean. "
United States
Anne
The price is AU$167
includes taxes & fees
3 Nov - 4 Nov
The Central Downtown Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1018)
"Good breakfast; pleasant staff on duty 24/7; convenient location."
United States
Dan and Alice
The price is AU$175
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Berkshire Hills Inn & Suites
Pool
Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham Williamstown
2.0 star property
6.6 out of 10, (894)
"A good location. Easy to find and access. Very clean and modern. "
United States
Adam
The price is AU$155
includes taxes & fees
26 Oct - 27 Oct
Howard Johnson by Wyndham Williamstown
Exterior detail
Williamstown Motel
Williamstown Motel
2.0 star property
9.4 out of 10, Exceptional, (307)
"It was clean and in a convenient location "
United States
Karen
The price is AU$129
includes taxes & fees
3 Nov - 4 Nov
Williamstown Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Huttopia Berkshires

Huttopia Berkshires

10/10 Excellent
"Healthy food too!"
GEORGINA 2-night trip
Posted 3 days ago
Huttopia Berkshires

More cheap accommodation in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd, South Deerfield, MA
The price is AU$161 per night from 2 Nov to 3 Nov
AU$161
2 Nov - 3 Nov
includes taxes & fees
7/10 Good! (1,025 reviews)

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Hotel Downstreet, an Ascend Collection Hotel and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of Windsor offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
What is staying in Windsor like?
Visitors can enjoy all that Windsor has to offer, including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodation options to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
Places to visit in the wider area include Mount Greylock State Reservation Visitor Center, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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