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Our top choices for Windsor hotels

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, (1,001 reviews)
"Comfy bed, nice front desk staff."
United States
Christina
The price is CA $121
CA $135 total
includes taxes & fees
Apr 26 - Apr 27
Red Roof Inn PLUS+ South Deerfield – Amherst

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (895 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is CA $109
CA $121 total
includes taxes & fees
Apr 14 - Apr 15
Berkshires Untold

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is CA $145
CA $229 total
includes taxes & fees
Apr 15 - Apr 16
Blooming Inn

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, (1,003 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is CA $153
CA $171 total
includes taxes & fees
Apr 14 - Apr 15
Best Western Plus Berkshire Hills Inn & Suites

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (28 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is CA $208
CA $232 total
includes taxes & fees
Apr 14 - Apr 15
The Revival House

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is CA $151
CA $166 total
includes taxes & fees
Apr 13 - Apr 14
Shaker Mill Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (897 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is CA $110
CA $129 total
includes taxes & fees
Apr 16 - Apr 17
Cozy Corner Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (783 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is CA $109
CA $122 total
includes taxes & fees
Apr 16 - Apr 17
The Villager Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is CA $128
CA $143 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Lee - Lenox South

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is CA $109
CA $122 total
includes taxes & fees
Apr 13 - Apr 14
Howard Johnson by Wyndham Lenox

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $203
CA $227 total
includes taxes & fees
Apr 19 - Apr 20
Element Lenox Berkshires

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $96
CA $106 total
includes taxes & fees
Apr 26 - Apr 27
Pleasant Valley Motel West Stockbridge

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
The price is CA $162
CA $178 total
includes taxes & fees
Apr 13 - Apr 14
The Springs Motel

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (901 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is CA $120
CA $165 total
includes taxes & fees
May 12 - May 13
Berkshire Mountain Lodge

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is CA $106
CA $118 total
includes taxes & fees
Apr 20 - Apr 21
Rodeway Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is CA $140
CA $156 total
includes taxes & fees
Apr 30 - May 1
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is CA $163
CA $182 total
includes taxes & fees
Apr 16 - Apr 17
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is CA $189
CA $212 total
includes taxes & fees
Apr 15 - Apr 16
Hideaway Inn Lenox

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is CA $145
CA $209 total
includes taxes & fees
Apr 13 - Apr 14
Becket Motel

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (292 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is CA $152
CA $170 total
includes taxes & fees
Apr 13 - Apr 14
The Whitlock
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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Frequently asked questions

What is the best area to stay in Windsor?
The best area to stay in Windsor is the main town centre, particularly around the historic Market Square and along Peascod Street.

This central area is the heart of Windsor, offering easy pedestrian access to many of the town's key attractions. You'll find a wide selection of shops, restaurants, and pubs here, all within a short stroll of Windsor Castle and the Long Walk. The streets are generally well-kept and easy to navigate.

Couples looking for a romantic getaway will find the town centre ideal. With the castle on your doorstep, charming cobbled streets, and a variety of dining options from casual to fine dining, it provides a refined and convenient base for exploring. You can easily spend your days touring the castle, enjoying a boat trip on the River Thames, or simply relaxing in one of the many cafes.

Families will also appreciate the convenience of staying in the town centre. Being close to the castle means less travel time with little ones, and there are several parks nearby, including Alexandra Gardens along the river, superb for children to play.
When is the best time to go to Windsor?
The best time to go to Windsor, Massachusetts, is during the summer months, from June to August, and the early autumn, specifically September and October.

Summer offers warm, pleasant weather, ideal for outdoor activities like hiking, fishing, and exploring the natural beauty of the Berkshire Mountains. The days are long, allowing ample time for sightseeing and enjoying the region's lakes and rivers. This is a great time for families looking for a relaxed holiday with plenty of fresh air and nature.

Early autumn brings cooler temperatures and the spectacular colours of the fall foliage. This period is particularly good for couples or solo travellers who appreciate scenic drives, photography, and outdoor adventures in a picturesque setting.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor.
How can I save on a Windsor hotel booking with Expedia?
Members always get our best prices. Find our best Windsor hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Windsor hotel?
Prices for hotels in Windsor often vary, but you can find a great deal from CA $121 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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