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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 24 Motels in Windsor with updated reviews, rates, and availability.

Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (717)
"Staff friendly. Room comfortable. Location great."
The price is AED 253
AED 283 total
includes taxes & fees
20 Apr - 21 Apr
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (839)
"Such nice people who run it. Nothing fancy but the people who work there are so friendly and accommodating "
The price is AED 367
AED 410 total
includes taxes & fees
19 Apr - 20 Apr
Howard Johnson by Wyndham Williamstown
The Villager Motel
Room, 1 King Bed | Desk, iron/ironing board, cribs/infant beds, rollaway beds

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (695)
"We stayed 2 nights. The staff were great . The non smoking rooms were awesome, very clean. Plenry of Hot water too.. Best value for yhe money 💰 Highly recommend...✌️🤠 "
The price is AED 253
AED 283 total
includes taxes & fees
20 Apr - 21 Apr
The Villager Motel
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (712)
"Friendly staff and quick checkin "
The price is AED 261
AED 292 total
includes taxes & fees
30 Apr - 1 May
FairBridge Inn Express
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (765)
"The location is convenient for the Pittsfield area and the room was very comfortable. "
The price is AED 316
AED 353 total
includes taxes & fees
20 Apr - 21 Apr
Berkshire Inn
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (807)
"The staff was super friendly. The room was very clean. Overall, a great experience. "
The price is AED 290
AED 342 total
includes taxes & fees
18 May - 19 May
Cozy Corner Motel
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (551)
"We were in Williamstown for a college tour, two adults three children, we had two rooms in this hotel , and it was just what we needed. Rooms big enough and in a good state, and a nice outside area. "
The price is AED 364
AED 406 total
includes taxes & fees
21 Apr - 22 Apr
Maple Terrace Motel
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (964)
"The room and bathroom were very clean. "
The price is AED 226
AED 248 total
includes taxes & fees
19 Apr - 20 Apr
Pleasant Valley Motel West Stockbridge
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 228
AED 255 total
includes taxes & fees
23 Apr - 24 Apr
Econo Lodge Lee - Great Barrington
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (906)
"Great motel, very clean, and great staff. recommended!"
The price is AED 278
AED 310 total
includes taxes & fees
1 May - 2 May
Willows Motel Williamstown
Blue Vista Motor Lodge
Terrace/patio

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (168)
"Lovely stay!"
The price is AED 656
AED 693 total
includes taxes & fees
20 Apr - 21 Apr
Blue Vista Motor Lodge
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (400)
"Staff friendly and helpful. "
The price is AED 248
AED 268 total
includes taxes & fees
1 May - 2 May
Berkshire Travel Lodge
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is AED 323
AED 361 total
includes taxes & fees
22 Apr - 23 Apr
Sunset Inn
Wagon Wheel Inn
Standard Room, 1 King Bed | View from room

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (601)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
18 Apr - 19 Apr
Wagon Wheel Inn
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (255)
"My husband and I visited Williamstown and N Adams for the first time. We were there for 5 nights. Rocky was not only a good host, he was a great guide. We loved his recommendations for food and local sights/events. The rooms were clean and comfortable as were the beds. We slept so soundly. We will definitely return. "
The price is AED 290
AED 324 total
includes taxes & fees
20 Apr - 21 Apr
Williamstown Motel
Heart of the Berkshires
Economy Cabin | Premium bedding, individually decorated, free WiFi, bed sheets

Heart of the Berkshires

9.4 out of 10, Exceptional, (3)
"Was great comfy quiet "
Heart of the Berkshires
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
8.8 out of 10, Excellent, (41)
"Springs Motel has a one of a kind vibe, loved the Double bed room! & managed by experienced, friendly people. Can’t wait to book a cabin next time with my family !! "
The price is AED 460
AED 505 total
includes taxes & fees
20 Apr - 21 Apr
The Springs Motel
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is AED 349
AED 513 total
includes taxes & fees
20 Apr - 21 Apr
Becket Motel
Northside Motel
Comfort Double Room, 2 Double Beds | Balcony

Northside Motel

2.0 star property
6.6 out of 10, (109)
"Stayed here for Solid Sound Festival since it’s a 10 min drive to Mass MOCA. It was exactly what you’d expect from a motel. Clean and comfortable. Perfectly met our needs. Coffee, orange juice, water cooler, and some pastries were offered in the office in the morning. It also looked like they were in the process of upgrading as mattresses and other items were being removed from some of the room the morning we left. We’d stay here again."
Northside Motel
Green Valley Motel
Free WiFi, bed sheets, alarm clocks

Green Valley Motel

2.0 star property
6.6 out of 10, (101)
"I felt that It was a dirty on the outisde and the paint chips on the outside took away the pleasant view of it "
Green Valley 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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Other property types in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1797)
"The location to jimney peak was great."
The price is AED 380
AED 458 total
includes taxes & fees
27 Apr - 28 Apr
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (927)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
21 Apr - 22 Apr
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.

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 938 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. Maple Terrace Motel: A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. Central Windsor is 15.7 mi (25.2 km) away. Berkshire Inn: Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking. Located 11.9 mi (19.2 km) from the heart of Windsor. The Villager Motel: Central Windsor is 17.8 mi (28.7 km) away. Free breakfast and free WiFi are available during your stay, along with room amenities like climate control. Williamstown Motel: 15.2 mi (24.4 km) from the heart of Windsor. Enjoy access to the library, and freebies including breakfast, WiFi, and parking.
What can I do in Windsor?
Some outdoorsy places nearby include Wahconah Falls State Park, Tannery Falls, and Mount Greylock State Reservation Visitor Center. You’ll find these family-friendly sights in the area: Berkshire Museum, Land of Providence, and Bousquet Ski Area. While you’re checking out the area, consider visiting Swift River, Mount Greylock, and Barrington Stage Company.
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.