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20 Aug - 21 Aug
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22 Aug - 24 Aug
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Top 10 Windsor hotels and places to stay

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Wonderful place to stay"
The price is 3.525.757 ₫
3.938.278 ₫ total
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is 3.329.882 ₫
3.719.479 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (687)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is 4.206.813 ₫
4.699.010 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Berkshires Untold
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1958)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is 2.847.924 ₫
3.469.555 ₫ total
includes taxes & fees
28 Aug - 29 Aug
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1008)
"Great location!"
The price is 3.999.013 ₫
4.466.898 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Hotel Downstreet, Ascend Hotel Collection
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is 3.356.963 ₫
4.777.613 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (523)
"Great place , love it, will return"
The price is 3.926.952 ₫
4.386.405 ₫ total
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (581)
"Amazing place to stay. Can’t wait to go again. "
The price is 1.731.132 ₫
2.521.506 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Berkshire Mountain Lodge
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"Loved our visit"
The price is 4.973.157 ₫
6.730.681 ₫ total
includes taxes & fees
26 Aug - 27 Aug
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (697)
"Pleasant stay"
The price is 2.405.981 ₫
3.054.604 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is 1.869.361 ₫
2.088.110 ₫ total
includes taxes & fees
2 Sept - 3 Sept
FairBridge Inn Express
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (863)
"Consistently a clean room with welcoming staff."
The price is 3.023.580 ₫
3.377.339 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (19)
"Really enjoyed my stay here, definitely need a car to get around"
The price is 3.553.364 ₫
3.969.107 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (867)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is 2.628.937 ₫
2.936.523 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Howard Johnson by Wyndham Williamstown
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (435)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is 1.774.447 ₫
1.987.412 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Berkshire Travel Lodge
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (728)
"Great quiet stay. "
The price is 2.339.988 ₫
2.613.688 ₫ total
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (625)
"It was lovely!"
The price is 1.676.115 ₫
1.872.221 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Econo Lodge Lee - Great Barrington
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (289)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is 2.342.617 ₫
2.616.703 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Very clean rooms and excellent staff."
The price is 2.793.262 ₫
3.120.074 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (756)
"Staff were excellent and welcoming."
The price is 4.706.268 ₫
5.256.822 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Hotel On North
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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Frequently asked questions

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.