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4 Stars Hotels in Windsor, Massachusetts from CA $186

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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, (633 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
United States
Sam
The price is CA $407
CA $455 total
includes taxes & fees
Jul 5 - Jul 6
The Williams Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is CA $166
CA $186 total
includes taxes & fees
Jun 30 - Jul 1
The Central Downtown Inn & Suites

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $467
CA $565 total
includes taxes & fees
Jul 12 - Jul 13
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, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $610
CA $681 total
includes taxes & fees
Jul 15 - Jul 16
Devonfield Inn B&B

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

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is CA $688
CA $807 total
includes taxes & fees
Jun 29 - Jun 30
The Inn at Stockbridge

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 $984
CA $1,099 total
includes taxes & fees
Jul 23 - Jul 24
33 Main

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
Lakehouse Inn

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 $427
CA $476 total
includes taxes & fees
Jun 25 - Jun 26
Hampton Terrace 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 $186

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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