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Find hotels in Windsor, MA from ฿2,322

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Check prices for these dates

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

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Our top choices for Windsor hotels

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Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is ฿2,251
฿2,522 total
includes taxes & fees
16 Jul - 17 Jul
Berkshire Travel Lodge
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,009 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
United States
Brian
The price is ฿5,061
฿5,653 total
includes taxes & fees
12 Jul - 13 Jul
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,004 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is ฿4,510
฿5,038 total
includes taxes & fees
15 Jul - 16 Jul
Best Western Plus Berkshire Hills Inn & Suites
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (925 reviews)
"Very nice and cute place to stay. Staff was very friendly and helpful. Room was nice and clean. Very quiet with beautiful outside property. The only problem was no coffee or breakfast until 8am."
United States
Tracy
The price is ฿2,951
฿3,469 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Corner Motel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,009 reviews)
"Great place"
United States
Michelle
The price is ฿4,790
฿5,350 total
includes taxes & fees
27 Jul - 28 Jul
Quality Inn Lee - Lenox South
Reception

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,005 reviews)
"Clean and convenient!"
United States
Katie
The price is ฿3,481
฿3,888 total
includes taxes & fees
12 Jul - 13 Jul
Red Roof Inn PLUS+ South Deerfield – Amherst
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ฿2,252
฿2,470 total
includes taxes & fees
14 Jul - 15 Jul
Pleasant Valley Motel West Stockbridge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (798 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is ฿3,303
฿3,689 total
includes taxes & fees
21 Jul - 22 Jul
The Villager Motel
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (918 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is ฿4,003
฿4,471 total
includes taxes & fees
13 Jul - 14 Jul
Howard Johnson by Wyndham Williamstown
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,006 reviews)
"Great value and excellent location"
United States
Truett
The price is ฿3,148
฿3,516 total
includes taxes & fees
13 Jul - 14 Jul
Willows Motel Williamstown
Room, 1 King Bed, Accessible, Non Smoking (Transfer Shower) | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is ฿5,693
฿6,359 total
includes taxes & fees
20 Jul - 21 Jul
Hotel Downstreet, an Ascend Collection Hotel
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (463 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ฿7,105
฿7,795 total
includes taxes & fees
20 Jul - 21 Jul
Shaker Mill Inn
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,429 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is ฿4,406
฿5,289 total
includes taxes & fees
2 Aug - 3 Aug
Vacation Village in the Berkshires
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (253 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
The price is ฿2,681
฿2,995 total
includes taxes & fees
20 Jul - 21 Jul
Rodeway Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (874 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is ฿3,002
฿3,353 total
includes taxes & fees
20 Jul - 21 Jul
Berkshire Inn
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (618 reviews)
"Adorable little place! Staff was incredible and the rooms were cute but the only downside was the rooms had an older home smell!"
United States
Stephanie
The price is ฿4,318
฿4,823 total
includes taxes & fees
19 Jul - 20 Jul
Maple Terrace Motel
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,008 reviews)
"Great service and friendly staff "
United States
Ly
The price is ฿7,790
฿8,702 total
includes taxes & fees
12 Jul - 13 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (690 reviews)
"Five Star stay!"
United States
Adeline
The price is ฿6,888
฿7,694 total
includes taxes & fees
26 Jul - 27 Jul
Hilton Garden Inn Lenox Pittsfield
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Great place"
United States
Luciane
The price is ฿3,303
฿3,689 total
includes taxes & fees
15 Jul - 16 Jul
Howard Johnson by Wyndham Lenox
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (675 reviews)
"Good location to towns in area"
United States
William
The price is ฿2,807
฿3,136 total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
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

The Yankee Inn

The Yankee Inn

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted 5 hours ago
The Yankee Inn

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is ฿2,078 per night from 26 Jul to 27 Jul
฿2,078
฿2,322 total
26 Jul - 27 Jul
includes taxes & fees
5.4/10 (848 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 The Yankee Inn and Berkshire Mountain Lodge. 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 Susan B. Anthony Birthplace Museum, Mount Greylock State Reservation Visitor Center and Skyline Trail. You'll also find Mount Greylock and Barrington Stage Company 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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