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27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sep - 7 Sep

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Top 10 Windsor hotels and places to stay

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, (1005)
"It’s the only place close to the Treehouse so we stayed there, it is definitely a RR Inn."
The price is ฿3,471
฿3,877 total
includes taxes & fees
3 Sept - 4 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is ฿2,688
฿4,594 total
includes taxes & fees
10 Sept - 11 Sept
Blooming Inn
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, (1003)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,105
฿4,585 total
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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
9.4 out of 10, Exceptional, (26)
"Do hotel, very clean we had a great day"
The price is ฿4,388
฿4,901 total
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (1004)
"Very clean rooms and excellent staff."
The price is ฿3,443
฿3,846 total
includes taxes & fees
28 Sept - 29 Sept
Best Western Plus Berkshire Hills Inn & Suites
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 ฿3,176
฿3,548 total
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (599)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is ฿2,893
฿3,231 total
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (731)
"Great quiet stay. "
The price is ฿2,889
฿3,227 total
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,560
฿2,860 total
includes taxes & fees
28 Sept - 29 Sept
Howard Johnson by Wyndham Lenox
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (63)
"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "
The price is ฿3,696
฿4,055 total
includes taxes & fees
1 Sept - 2 Sept
The Springs Motel
Element Lenox Berkshires
Lobby lounge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is ฿4,935
฿5,512 total
includes taxes & fees
3 Sept - 4 Sept
Element Lenox Berkshires
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (941)
"Comfortable, clean, and great continental breakfast options! "
The price is ฿2,893
฿3,231 total
includes taxes & fees
1 Sept - 2 Sept
Willows Motel Williamstown
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1008)
"Great location!"
The price is ฿4,890
฿5,462 total
includes taxes & fees
28 Sept - 29 Sept
Hotel Downstreet, an Ascend Collection Hotel
The Revival House
Romantic Room, 1 King Bed (Room 4) | 1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.0 out of 10, Wonderful, (12)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
The price is ฿5,844
฿6,528 total
includes taxes & fees
1 Sept - 2 Sept
The Revival House
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (697)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ฿5,207
฿5,816 total
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold
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, (1002)
"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 ฿4,138
฿5,890 total
includes taxes & fees
28 Sept - 29 Sept
The Cornell Inn, Lenox & The Berkshires
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great staff! Comfortable bed! "
The price is ฿4,656
฿5,201 total
includes taxes & fees
28 Sept - 29 Sept
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (572)
"Fabulous place"
The price is ฿4,935
฿5,512 total
includes taxes & fees
2 Sept - 3 Sept
Courtyard by Marriott Lenox Berkshires
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (848)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is ฿2,747
฿3,232 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Corner 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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Learn more about Windsor

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Top Windsor Hotel Reviews

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 ฿2,560 per night from 28 Sept to 29 Sept
฿2,560
฿2,860 total
28 Sept - 29 Sept
includes taxes & fees
7.4/10 Good! (758 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Berkshire Mountain Lodge and FairBridge Inn Express. See all available top hotels, or 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.