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Check prices for these dates

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12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
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30 Jan - 1 Feb

Motels in Windsor

Front of property
Becket Motel

Becket Motel

2.5 star property
Becket
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
The price is SAR 342
SAR 508 total
includes taxes & fees
5 Dec - 6 Dec
Becket Motel
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

2.0 star property
North Adams
9.8 out of 10, Exceptional, (195)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is SAR 670
SAR 708 total
includes taxes & fees
7 Dec - 8 Dec
Blue Vista Motor Lodge
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is SAR 328
SAR 366 total
includes taxes & fees
10 Dec - 11 Dec
Sunset Inn
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is SAR 301
SAR 336 total
includes taxes & fees
18 Dec - 19 Dec
FairBridge Inn Express
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
Lee
6.4 out of 10, (648)
"Great place. , good staff "
United States
ketul
The price is SAR 220
SAR 246 total
includes taxes & fees
21 Dec - 22 Dec
Econo Lodge Lee - Great Barrington
Property grounds
Wagon Wheel Inn

Wagon Wheel Inn

2.0 star property
Lenox
7.0 out of 10, Good, (641)
"Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon."
United States
Benjamin
The price is SAR 259
SAR 289 total
includes taxes & fees
7 Dec - 8 Dec
Wagon Wheel Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is SAR 296
SAR 331 total
includes taxes & fees
5 Dec - 6 Dec
Howard Johnson by Wyndham Lenox
Exterior detail
Williamstown Motel

Williamstown Motel

2.0 star property
Williamstown
9.4 out of 10, Exceptional, (314)
"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."
United States
DAVID
The price is SAR 331
SAR 369 total
includes taxes & fees
11 Dec - 12 Dec
Williamstown Motel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is SAR 297
SAR 332 total
includes taxes & fees
17 Dec - 18 Dec
Berkshire Inn
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (991)
"Warm welcome. Great location. Best fresh fruit breakfast ever."
United States
Melissa
The price is SAR 287
SAR 321 total
includes taxes & fees
18 Dec - 19 Dec
Willows Motel Williamstown
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (586)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is SAR 372
SAR 415 total
includes taxes & fees
18 Dec - 19 Dec
Maple Terrace Motel
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
The price is SAR 280
SAR 331 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Corner Motel
Courtyard
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is SAR 453
SAR 497 total
includes taxes & fees
8 Dec - 9 Dec
The Springs Motel
Exterior
The Villager Motel

The Villager Motel

2.0 star property
Williamstown
8.8 out of 10, Excellent, (763)
"It's very good for stay over"
United States
Frances
The price is SAR 259
SAR 289 total
includes taxes & fees
18 Dec - 19 Dec
The Villager Motel
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
The price is SAR 197
SAR 216 total
includes taxes & fees
1 Jan - 2 January 2026
Pleasant Valley Motel West Stockbridge
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

2.5 star property
Austerlitz
5.4 out of 10, (458)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is SAR 257
SAR 288 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Travel Lodge
Pool
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

2.0 star property
Williamstown
6.6 out of 10, (899)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is SAR 338
SAR 377 total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Williamstown
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 3 days ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

What can I expect from a motel trip to Windsor?
If you're having a hard time finding motels in Windsor, let us help you find a motel or something similar from over 976 accommodations in the area. Simply filter using our search tools by price per night or cost-effective amenities such as free parking and free breakfast.
What's it like to stay in a motel?
At many motels, you'll often find a free parking spot and an outdoor pool. When you stay at a motel property, you'll usually access your room from an outside corridor overlooking the parking lot. The word "motel" was conceived in 1925 in San Luis Obispo, California by the owner of the Milestone Mo-Tel.
What are the best motels in Windsor?
Here are some of our customers' favorite motels in the larger area. Howard Johnson by Wyndham Lenox is located 13.4 mi (21.6 km) from the heart of Windsor. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. The Springs Motel: A seasonal outdoor pool, free WiFi, and free parking are available during your stay. Central Windsor is 11.7 mi (18.9 km) away. FairBridge Inn Express: Enjoy access to the business center, and freebies including WiFi and parking. Located 8.5 mi (13.6 km) from the heart of Windsor. Maple Terrace Motel: Central Windsor is 15.7 mi (25.2 km) away. A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. The Villager Motel: 17.8 mi (28.7 km) from the heart of Windsor. Enjoy the in-room free WiFi, and freebies including breakfast and parking.
What can I do in Windsor?
Some outdoorsy places nearby include Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Skyline Trail. You'll find these family-friendly sights in the area: Berkshire Museum, Bousquet Ski Area, and Berkshire Scenic Railway Museum. While you're checking out the area, consider visiting Crane Museum of Papermaking, Swift River, and Mount Greylock.
What's the weather like in Windsor?
Weather can make or break a roadtrip, so here's some data about year-round temperatures in Windsor to help you plan yours: The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are my options for getting around Windsor when staying in a motel?
We've gathered some information about getting around Windsor to help you navigate your stay: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away from the heart of the city. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.