Hotels in Windsor

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Check prices for these dates

Tonight
Mar 18 - Mar 19
Tomorrow
Mar 19 - Mar 20
This weekend
Mar 20 - Mar 22
Next weekend
Mar 27 - Mar 29

Where to stay in Windsor?

Lobby lounge
Berkshires Untold
Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (876 reviews)
  • cleanliness
    Enjoy luxury and culture in the Berkshires with nearby Tanglewood Music Center access.
The price is $78
$87 total
includes taxes & fees
Mar 29 - Mar 30
Berkshires Untold
55-inch LCD TV with digital channels, printers
The Revival House
The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (26 reviews)
  • cleanliness
    Tranquil guesthouse in Adams with free breakfast and easy access to local attractions.
The price is $138
$154 total
includes taxes & fees
Mar 29 - Mar 30
The Revival House
Desk, laptop workspace, blackout drapes, iron/ironing board
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
  • cleanliness
    Charming Berkshires motel near Tanglewood with free WiFi and convenient parking.
The price is $65
$71 total
includes taxes & fees
Mar 19 - Mar 20
Pleasant Valley Motel West Stockbridge
Exterior
Hideaway Inn Lenox
Hideaway Inn Lenox
2.0 star property
Lenox
The price is $156
$174 total
includes taxes & fees
Mar 23 - Mar 24
Hideaway Inn Lenox
Lobby lounge
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (23 reviews)
  • cleanliness
    Unwind in the Berkshires with a cozy indoor pool near Tanglewood Music Center.
The price is $139
$155 total
includes taxes & fees
Mar 26 - Mar 27
Element Lenox Berkshires
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Relaxing Berkshire retreat near Tanglewood with free breakfast and mountain recreation.
The price is $107
$119 total
includes taxes & fees
Mar 30 - Mar 31
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Blooming Inn
Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
  • cleanliness
    Charming guesthouse near Glacial Potholes offers free WiFi and winter adventures.
The price is $94
$154 total
includes taxes & fees
Mar 19 - Mar 20
Blooming Inn
Lobby sitting area
Berkshire Travel Lodge
Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
The price is $70
$78 total
includes taxes & fees
Mar 21 - Mar 22
Berkshire Travel Lodge
Lobby
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    A cozy retreat 15 minutes from Tanglewood Music Center with complimentary WiFi.
The price is $84
$94 total
includes taxes & fees
Apr 6 - Apr 7
Quality Inn Lee - Lenox South
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets
Rodeway Inn
Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (239 reviews)
The price is $72
$80 total
includes taxes & fees
Mar 25 - Mar 26
Rodeway Inn
Miscellaneous
1896 House Country Inn & Motels
1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (449 reviews)
  • cleanliness
    Peaceful inn nestled among Williamstown attractions with restaurant and bar.
The price is $125
$140 total
includes taxes & fees
Mar 19 - Mar 20
1896 House Country Inn & Motels
Gazebo
Cozy Corner Motel
Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (896 reviews)
The price is $79
$93 total
includes taxes & fees
Mar 19 - Mar 20
Cozy Corner Motel
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (839 reviews)
  • cleanliness
    Experience Lenox from a central motel with a pool and friendly staff at your service.
The price is $79
$88 total
includes taxes & fees
Mar 19 - Mar 20
Howard Johnson by Wyndham Lenox
Reception
The Villager Motel
The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (780 reviews)
  • cleanliness
    Explore Williamstown's scenic charm from this well-positioned motel in the Berkshires.
The price is $75
$84 total
includes taxes & fees
Mar 19 - Mar 20
The Villager Motel
Lake
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Tranquil lakefront escape with stunning sunset views and a 24-hour fitness center.
The price is $92
$103 total
includes taxes & fees
Apr 7 - Apr 8
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard
The Springs Motel
The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (94 reviews)
  • cleanliness
    Cozy lodging near Jiminy Peak offers outdoor relaxation at seasonal pool.
The price is $123
$135 total
includes taxes & fees
Mar 22 - Mar 23
The Springs Motel
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Unwind in Lenox with mountain vistas, seasonal pools, and easy Berkshire access.
The price is $88
$99 total
includes taxes & fees
Mar 23 - Mar 24
The Yankee, Trademark Collection by Wyndham
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144 reviews)
The price is $174
$194 total
includes taxes & fees
Mar 19 - Mar 20
The Trail in Adams - Berkshires’ Art Hotel
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 reviews)
  • cleanliness
    Lakeside getaway in Berkshires with indoor pool and Tanglewood Music Center nearby.
The price is $132
$147 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
In-room dining
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (659 reviews)
  • cleanliness
    Cozy retreat near Lee Premium Outlets with mini golf and continental breakfast.
The price is $67
$75 total
includes taxes & fees
Apr 1 - Apr 2
Econo Lodge Lee - Great Barrington
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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Check out reviews of Windsor hotels guests love

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Clean, quiet, and a great breakfast! The staff was friendly. We enjoyed a fire in our room and the free bottle of wine. "
Jill 1-night trip
Posted 5 hours ago
The Cornell Inn, Lenox & The Berkshires

Frequently asked questions

What accommodations do travelers like in Windsor?
Guests like FairBridge Inn Express.
Can I book refundable hotels in Windsor?
If you need the flexibility to change your travel plans to Windsor, most accommodations offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Windsor be like during my trip?
July and August are typically the warmest months in Windsor when the average temp is 63°F. January and February are the coldest months when the average temperature is 25°F. July and August are the months with the most rain.
Why should I book my Windsor hotel with Hotels.com?
There are lots of reasons to book your Windsor trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.