4 Stars Hotels in Windsor, Massachusetts from CA $156

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Our top choices for Windsor 4-star hotels

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (597 reviews)
"one of my favorite places to stay..."
United States
Augusta
The price is CA $270
CA $302 total
includes taxes & fees
Mar 23 - Mar 24
The Williams Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (359 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is CA $140
CA $156 total
includes taxes & fees
Mar 23 - Mar 24
The Central Downtown Inn & Suites

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is CA $182
CA $214 total
includes taxes & fees
Apr 3 - Apr 4
Lakehouse Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $425
CA $514 total
includes taxes & fees
Apr 5 - Apr 6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $328
CA $384 total
includes taxes & fees
Mar 27 - Mar 28
The Inn at Stockbridge

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $624
CA $698 total
includes taxes & fees
Mar 29 - Mar 30
33 Main

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is CA $300
CA $336 total
includes taxes & fees
Mar 24 - Mar 25
Hampton Terrace Inn

Garden Gables Inn

Garden Gables Inn
4.0 star property
Lenox
9.2 out of 10, Wonderful, (57 reviews)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
United States
john
Garden Gables Inn

Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
4.0 star property
Hancock
Family-friendly Hancock Home: Walk to Slopes!
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Top Windsor Hotel Reviews

Find out more about Windsor

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windsor are calling your name. Known for providing first-rate service in amazing locations, each of the Windsor 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Windsor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windsor, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windsor hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
With Expedia's handy filter tool, locking in a terrific deal on a 4-star hotel in Windsor just got simpler. Start by entering your chosen travel dates and length of your stay. Then sort the results by price and pick the option that best suits your budget and style.

  • Search for the lowest price from CA $156

What's the difference between 5-star and 4-star hotels in Windsor?
If you decide to book a stay at a 4-star hotel in Windsor, you'll typically find lots of conveniences to keep you relaxed, such as a restaurant, gym and pool. You can look forward to excellent service and upmarket accommodations. Go for a 5-star hotel and you'll get a few more perks — think concierge assistance, on-site spas and nightly turndown services. You'll most likely get extra amenities and premium services at a 5-star getaway, though both are fabulous options for luxury travellers.
Does Windsor have any 4-star all-inclusive resorts?
Finding vacation bliss in Windsor is as easy as entering in your destination and dates, and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your meals, accommodations, entertainment and activities, or choose a standard 4-star resort in or around this top destination.

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