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Luxury Hotels & Resorts in Windsor from AU$109

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Check availability on Windsor Luxury Hotels

Our top choices for Windsor luxury hotels

Front of property – evening/night

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (634 reviews)
The price is AU$500
includes taxes & fees
7 July - 8 July
The Williams Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is AU$741
includes taxes & fees
20 July - 21 July
The Inn at Stockbridge
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
The price is AU$678
includes taxes & fees
29 June - 30 June
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is AU$1,282
includes taxes & fees
7 July - 8 July
33 Main
Suite, Private Bathroom (RedBird Suite) | View from room

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)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is AU$578
includes taxes & fees
12 July - 13 July
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is AU$567
includes taxes & fees
20 July - 21 July
Hampton Terrace Inn
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is AU$173
includes taxes & fees
1 July - 2 July
The Central Downtown Inn & Suites
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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Top Windsor Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"The hot tub was welcomed after a long day of hiking the Berkshires!"
Linda 1-night trip
Posted 4 hours ago
The Yankee Inn

Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Windsor?
Expedia can help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Westfield, MA (BAF-Barnes Municipal) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a trip, so we make it easy to get what you want to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Windsor has to offer.
When can I expect good weather in Windsor?
Planning for the weather is a good way to make your trip to Windsor relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What's there to see and do in Windsor?
Enjoy Windsor with a stop at Susan B. Anthony Birthplace Museum, Berkshire Scenic Railway Museum and Mount Greylock State Reservation Visitor Center. If you have some spare time during your trip, you might want to check out Skyline Trail and Swift River.

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