Find hotels in Windsor, MA from 2.329.801 ₫

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28 Sep - 29 Sep
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29 Sep - 30 Sep
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3 Oct - 5 Oct
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10 Oct - 12 Oct

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Top 10 Windsor hotels and places to stay

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1018)
"Great Indian restaurant in the hotel!"
The price is 3.029.744 ₫
3.384.224 ₫ total
includes taxes & fees
27 Oct - 28 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (735)
"Rooms are a clean and upgraded motel. Nice lobby and rooms. "
The price is 3.369.973 ₫
3.764.261 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1012)
"Nice area to visit "
The price is 3.065.388 ₫
3.424.205 ₫ total
includes taxes & fees
1 Oct - 2 Oct
The Yankee, Trademark Collection by Wyndham
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, (1005)
"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 3.371.135 ₫
4.797.783 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2022)
"Clean room, friendly staff, affordable."
The price is 2.616.242 ₫
3.211.983 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1012)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is 3.825.267 ₫
4.272.823 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (662)
"It was a great Stay where we had to it was a good area I would come back to this place again "
The price is 2.460.826 ₫
3.338.586 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Berkshire Mountain Lodge
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, (739)
"The lodging was convenient to all the area attractions."
The price is 3.421.829 ₫
4.190.768 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (45)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is 3.343.940 ₫
3.735.182 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is 2.587.494 ₫
2.890.231 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Huttopia Berkshires
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, (883)
"Our stay was very pleasant "
The price is 2.590.134 ₫
2.893.180 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (775)
"Great property! Very large clean room in a unique hotel! "
The price is 4.726.137 ₫
5.279.095 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Hotel On North
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1009)
"great place have stayed several times, and hope to return."
The price is 4.726.137 ₫
6.458.781 ₫ total
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (546)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is 3.974.972 ₫
4.439.929 ₫ total
includes taxes & fees
29 Oct - 30 Oct
The Constance by the Lenox Collection
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (301)
"It was clean and in a convenient location "
The price is 3.405.987 ₫
3.804.488 ₫ total
includes taxes & fees
29 Sept - 30 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, (1012)
"Great property would certainly stay again."
The price is 3.007.566 ₫
3.359.451 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Best Western Plus Berkshire Hills Inn & Suites
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (508)
"Great hotel, staff and restaurant!"
The price is 6.261.471 ₫
6.994.063 ₫ total
includes taxes & fees
29 Oct - 30 Oct
The Williams Inn
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (743)
"Perfect location for our passing through vacay."
The price is 2.349.867 ₫
2.624.722 ₫ total
includes taxes & fees
29 Sept - 30 Sept
The Villager Motel
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.6 out of 10, (882)
"All good except needs updating in rooms and add a microwave, more updated breakfast room needed."
The price is 2.904.066 ₫
3.243.842 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Howard Johnson by Wyndham Williamstown
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout curtains, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1016)
"excellent value for the price"
The price is 2.589.897 ₫
2.892.915 ₫ total
includes taxes & fees
1 Oct - 2 Oct
Red Roof Inn PLUS+ South Deerfield – Amherst
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

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
Marti 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Huttopia Berkshires

Huttopia Berkshires

10/10 Excellent
"Great Time! Beautiful new tents with all the items you need to Glamp with from silverware to tupperware. Comfy beds and comforter! Everyone was so nice and you know they love what they do! Next fall/foiliage camping in the trapper with the wood stove !"
Melissa 3-night trip
Posted 1 month ago
Huttopia Berkshires

More cheap stays in Windsor

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is 2.085.837 ₫ per night from 29 Sept to 30 Sept
2.085.837 ₫
2.329.801 ₫ total
29 Sept - 30 Sept
includes taxes & fees
7.4/10 Good! (802 reviews)

Hotels in Windsor with star rating

Hotels in Windsor with star rating

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.

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