Title: The Best 5 Star Hotels in Windsor, MA from $113 | Expedia.com

[Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides)

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## Check availability on Windsor 5 Star Hotels

Tonight

[Feb 6 - Feb 7](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 7 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-07&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windsor.

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Williams Inn

101 Spring Street Williamstown MA

$208 nightly

$233 total

Mar 9 - Mar 10

Total with taxes and fees

9.6/10 Exceptional! (572 reviews)

[](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information)

![The Central Downtown Inn & Suites](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA

$101 nightly

$113 total

Mar 1 - Mar 2

Total with taxes and fees

8.6/10 Excellent! (354 reviews)

[](https://expedia.com/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

![Lakehouse Inn](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Lakehouse Inn

615 Laurel St. Lee MA

$141 nightly

$158 total

Feb 7 - Feb 8

Total with taxes and fees

9.6/10 Exceptional! (291 reviews)

[](https://expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Windsor.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50)

You can also use these popular filters to refine your search.

[Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026&regionId=6005427&star=50&star=50&amenities=WATER_PARK)

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.

## Top Windsor Hotel Reviews

## Find out more about Windsor

Why not demand the best of accommodations on your trip to Windsor? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Windsor so popular in the last year. There's no reason to delay a getaway to Windsor any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Windsor are the perfect places to relax in during your next escape. Don't wait any longer!

### 5-Star Hotels in Windsor

You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and attentive guest service are all waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A reflexology treatment that will leave you feeling outstanding? Butler services? No matter what you want on a perfect getaway, you're bound to find it here. 

But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Windsor are waiting for you to rest up after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. 

### Make Your Escape

The results are in, and Windsor 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Decide on one of Expedia's Windsor 5-star hotels today and settle down in total tranquility tomorrow.

## Frequently asked questions

### How much does it cost to stay in a 5-star hotel in Windsor?

> - Search for the lowest price per night from $113

### What makes a hotel 5 stars in Windsor?

### Are there any 5-star all-inclusive resorts in Windsor?

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