Luxury Hotels & Resorts in Windsor from AU$94

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Windsor Luxury Hotels

This weekend
Next weekend

Our top choices for Windsor luxury hotels

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
The price is AU$415
includes taxes & fees
11 May - 12 May
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)
The price is AU$426
includes taxes & fees
25 May - 26 May
The Inn at Stockbridge

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (623 reviews)
The price is AU$441
includes taxes & fees
26 May - 27 May
The Williams 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, (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$517
includes taxes & fees
25 May - 26 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is AU$457
includes taxes & fees
28 May - 29 May
Hampton Terrace Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (363 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is AU$164
includes taxes & fees
31 May - 1 June
The Central Downtown Inn & Suites

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is AU$1,008
includes taxes & fees
10 May - 11 May
33 Main
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

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 Wahconah Falls State Park, Susan B. Anthony Birthplace Museum and Mount Greylock State Reservation Visitor Center. If you have some spare time during your trip, you might want to check out Swift River and Mount Greylock.

Explore a world of travel with Expedia