Compare and book 4 Star hotels in Windsor, Massachusetts

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Top Windsor 4 Star Hotels

The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (485)
"The property was spacious but still had a cozy feel. "
The price is 6.126.334 ₫
6.843.115 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Williams Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (301)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is 3.020.130 ₫
3.373.617 ₫ total
includes taxes & fees
4 Sept - 5 Sept
The Central Downtown Inn & Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is 16.256.178 ₫
18.158.151 ₫ total
includes taxes & fees
27 Aug - 28 Aug
33 Main
Seven Hills Inn
Front of property

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
Seven Hills Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is 10.301.795 ₫
12.462.255 ₫ total
includes taxes & fees
27 Aug - 28 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Hampton Terrace Inn
Exterior

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is 8.637.572 ₫
9.648.134 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Hampton Terrace Inn
Garden Gables Inn
Front of property – evening/night

Garden Gables Inn

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

How much does it cost to stay in a 4-star hotel in Windsor?
We can help you easily track down the perfect 4-star hotel for your getaway in Windsor. Use our handy filter tool to fine-tune your search by things like price, amenities and property star rating and get access to unbeatable deals in a few clicks.

  • Search for the lowest price from 3.020.130 ₫

What's the difference between 5-star and 4-star hotels in Windsor?
Give yourself the luxury treatment during your Windsor getaway by checking in to a 4-star hotel. As well as featuring upscale surroundings, these retreats are typically packed with amenities, including large beds, bathrobes and more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and memorable one. 24-hour front desk, elegant furnishings and gourmet dining are just the start of the superior services and conveniences you'll likely get access to.
Does Windsor have any 4-star all-inclusive resorts?
Finding your dream holiday in Windsor is as easy as typing in your travel details and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodation, meals, activities and entertainment, or opt for a standard 4-star resort in or around this leading destination.