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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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, (716)
"No issues"
The price is AED 253
AED 283 total
includes taxes & fees
19 Mar - 20 Mar
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 331
AED 369 total
includes taxes & fees
20 Mar - 21 Mar
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (690)
"The front desk staff was really nice and check in was very quick. My king bed room was great. It smelled fresh and was very clean. There’s a mini fridge, coffee maker, and a microwave. The bathroom was stocked nicely with towels and soaps as well as a hair dryer. Outside there are cute chairs and some swings on the property. This was a very budget friendly place and will definitely come back again!"
The price is AED 253
AED 283 total
includes taxes & fees
19 Mar - 20 Mar
The Villager Motel
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (764)
"The room was very clean "
The price is AED 316
AED 353 total
includes taxes & fees
19 Mar - 20 Mar
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (708)
"Friendly staff and quick checkin "
The price is AED 228
AED 255 total
includes taxes & fees
31 Mar - 1 Apr
FairBridge Inn Express
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (547)
"This is a great place to escape to in the Berkshires. Convenient location, quiet neighborhood, and great spots to eat."
The price is AED 345
AED 386 total
includes taxes & fees
20 Mar - 21 Mar
Maple Terrace Motel
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.0 out of 10, Wonderful, (800)
"The Staff were wonderful. Location great if visiting Mass MOCA and/or Clark Museum. Good dining options nearby as well"
The price is AED 309
AED 363 total
includes taxes & fees
19 Mar - 20 Mar
Cozy Corner Motel
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (905)
"Great motel, very clean, and great staff. recommended!"
The price is AED 294
AED 329 total
includes taxes & fees
31 Mar - 1 Apr
Willows Motel Williamstown
Blue Vista Motor Lodge
Single Room | In-room safe, desk, free WiFi, bed sheets

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (166)
"We had such a great stay at the Blue Vista Motor Lodge. The staff we encountered were welcoming and lovely. The room was super clean and had everything we needed for a comfortable stay. And the view! Incredible. "
The price is AED 578
AED 611 total
includes taxes & fees
19 Mar - 20 Mar
Blue Vista Motor Lodge
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 223
AED 245 total
includes taxes & fees
23 Mar - 24 Mar
Pleasant Valley Motel West Stockbridge
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (398)
"Staff friendly and helpful. "
The price is AED 241
AED 261 total
includes taxes & fees
31 Mar - 1 Apr
Berkshire Travel Lodge
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is AED 253
AED 283 total
includes taxes & fees
19 Mar - 20 Mar
Wagon Wheel Inn
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 220
AED 246 total
includes taxes & fees
26 Mar - 27 Mar
Econo Lodge Lee - Great Barrington
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...
The price is AED 295
AED 330 total
includes taxes & fees
26 Mar - 27 Mar
Sunset Inn
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (253)
"Very helpful, friendly, and attentive owners"
The price is AED 290
AED 324 total
includes taxes & fees
19 Mar - 20 Mar
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 "
The price is AED 271
AED 356 total
includes taxes & fees
19 Mar - 20 Mar
Heart of the Berkshires
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
8.8 out of 10, Excellent, (40)
"The outdoor fire pits and setting areas looked like a blast but it rained so we didn’t get a chance to hang outside. Next time! "
The price is AED 418
AED 459 total
includes taxes & fees
19 Mar - 20 Mar
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
19 Mar - 20 Mar
Becket Motel
Northside Motel
Exterior

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
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1791)
"Property needs a little upgrade."
The price is AED 437
AED 520 total
includes taxes & fees
24 Mar - 25 Mar
Vacation Village in the Berkshires
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
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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 941 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 Williamstown is located 15 mi (24.2 km) from the heart of Windsor. Enjoy access to the business center, and freebies including breakfast, WiFi, and parking. The Villager Motel: Free breakfast, free WiFi, and free parking are available during your stay. Central Windsor is 17.8 mi (28.7 km) away. Howard Johnson by Wyndham Lenox: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 13.4 mi (21.6 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. Berkshire Inn: 11.9 mi (19.2 km) from the heart of Windsor. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking.
What can I do in Windsor?
Some outdoorsy places nearby include Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Swift River. You’ll find these family-friendly sights in the area: Berkshire Museum, Bousquet Ski Area, and Shelburne Falls Bowling Alley. While you’re checking out the area, consider visiting Mount Greylock, Barrington Stage Company, and Colonial Theater.
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.