Find hotels in Windsor, MA from SAR 253

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Tonight
19 Jun - 20 Jun
Tomorrow
20 Jun - 21 Jun
This weekend
20 Jun - 22 Jun
Next weekend
27 Jun - 29 Jun

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Compare 968 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (824)
"Great classic motel. Clean. Friendly, helpful staff."
The price is SAR 334
SAR 392 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Corner Motel
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (390)
"Phenomenal room, staff and location! We loved The Porches!!"
The price is SAR 740
SAR 910 total
includes taxes & fees
23 Jun - 24 Jun
The Porches Inn at Mass MoCA
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (545)
"Great, and quiet place. Friendly staff!"
The price is SAR 555
SAR 620 total
includes taxes & fees
24 Jun - 25 Jun
Berkshire Valley Inn
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (736)
"Best hotel in the Berkshire! "
The price is SAR 574
SAR 641 total
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
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, (1000)
"Great place to stay "
The price is SAR 380
SAR 424 total
includes taxes & fees
1 Jul - 2 Jul
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (656)
"Wonderful property we’ve been coming here for years"
The price is SAR 469
SAR 577 total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (86)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is SAR 709
SAR 766 total
includes taxes & fees
23 Jun - 24 Jun
Inn at Silver Maple Farm
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1830)
"Love it's peace and beautiful~"
The price is SAR 390
SAR 477 total
includes taxes & fees
22 Jun - 23 Jun
Vacation Village in the Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is SAR 656
SAR 900 total
includes taxes & fees
23 Jun - 24 Jun
The Red Lion Inn
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (933)
"Amazing place!"
The price is SAR 597
SAR 666 total
includes taxes & fees
22 Jun - 23 Jun
Jiminy Peak Mountain Resort
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (714)
"Nice clean spot that was convenient and affordable."
The price is SAR 334
SAR 373 total
includes taxes & fees
22 Jun - 23 Jun
The Villager Motel
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (313)
"Gorgeous place with clean room and excellent areas to have breakfast, read, and relax. Friendly staff and easy checking process. Would stay here again!"
The price is SAR 660
SAR 738 total
includes taxes & fees
24 Jun - 25 Jun
The Dewey
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is SAR 702
SAR 784 total
includes taxes & fees
22 Jun - 23 Jun
Hilton Garden Inn Lenox Pittsfield
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Quiet, clean, great proximity to places and destinations. "
The price is SAR 446
SAR 499 total
includes taxes & fees
30 Jun - 1 Jul
The Yankee, Trademark Collection by Wyndham
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (412)
"Nice"
The price is SAR 529
SAR 580 total
includes taxes & fees
23 Jun - 24 Jun
Shaker Mill Inn
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (172)
"Lovely stay!"
The price is SAR 749
SAR 792 total
includes taxes & fees
22 Jun - 23 Jun
Blue Vista Motor Lodge
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (474)
"Staff was incredibly nice & helpful, and the stay was very comfortable. We’d definitely stay there again."
The price is SAR 578
SAR 646 total
includes taxes & fees
23 Jun - 24 Jun
The Constance by the Lenox Collection
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."
The price is SAR 539
SAR 602 total
includes taxes & fees
21 Jul - 22 Jul
Hotel Downstreet, Ascend Hotel Collection
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (559)
"A great place to stay in Williamstown. Beautiful garden, friendly staff, very comfortable."
The price is SAR 431
SAR 482 total
includes taxes & fees
25 Jun - 26 Jun
Maple Terrace 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

Explore Windsor: its food and more!

See all hotels in Windsor

More cheap stays in Windsor

More cheap stays in Windsor

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd, South Deerfield, MA
The price is SAR 385 per night from Jun 24 to Jun 25
SAR 385
SAR 430 total
24 Jun - 25 Jun
includes taxes & fees
7/10 Good! (1,008 reviews)

Hotels in Windsor with star-rating

Hotels in Windsor with star-rating

Recent reviews of Windsor hotels

Recent reviews of Windsor hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Sweet hotel with lovely lake in back"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 13 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection

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?

Red Roof Inn PLUS+ South Deerfield – Amherst, located 22.1 mi (35.5 km) from the heart of Windsor, is a top choice for your stay based on our traveler data. Other good options for your visit to the area are The Yankee, Trademark Collection by Wyndham and Vacation Village in the Berkshires. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental in Windsor?

Deluxe Queen Room with 2 Queen Beds: This vacation home rental outside of Windsor is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay. See all vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

Where can I learn more about changing or cancelling my trip to Windsor?

For more information about updating your trip to Windsor or cancelling it, click here.

What's the best hotel for staying near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations 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 Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Swift River. You'll also find Mount Greylock and Barrington Stage Company in the area. Check out what more to see and do in Expedia's Windsor guide.

What's the seasonal weather like in Windsor?

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.