Hotels in Windsor

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Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,002 reviews)
  • cleanliness
    Relax near UMass Amherst with free WiFi and parking at this convenient South Deerfield hotel.
The price is $85
$95 total
includes taxes & fees
Apr 1 - Apr 2
Red Roof Inn PLUS+ South Deerfield – Amherst
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 24 - Mar 25
Blooming Inn
UU Rowe Camp and Conference Center
UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
The price is $225
$238 total
includes taxes & fees
Mar 24 - Mar 25
UU Rowe Camp and Conference Center
12-acre Vacation Rental in the Berkshires!
12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is $243
$545 total
includes taxes & fees
Mar 24 - Mar 25
12-acre Vacation Rental in the Berkshires!
Becket Motel
Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
  • cleanliness
    Contemporary Berkshires retreat with natural surroundings and nearby trails.
The price is $95
$140 total
includes taxes & fees
Apr 7 - Apr 8
Becket Motel
Blue Vista Motor Lodge
Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (207 reviews)
  • cleanliness
    Tranquil retreat in North Adams with hot tubs and sauna for ultimate relaxation.
The price is $182
$192 total
includes taxes & fees
Mar 24 - Mar 25
Blue Vista Motor Lodge
Rodeway Inn
Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
The price is $72
$80 total
includes taxes & fees
Mar 29 - Mar 30
Rodeway Inn
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 24 - Mar 25
The Trail in Adams - Berkshires’ Art Hotel
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 $150
$168 total
includes taxes & fees
Mar 24 - Mar 25
The Revival House
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
The price is $118
$132 total
includes taxes & fees
Apr 6 - Apr 7
Hotel Downstreet, an Ascend Collection Hotel
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (461 reviews)
The price is $169
$211 total
includes taxes & fees
Mar 24 - Mar 25
The Porches Inn at Mass MoCA
Harbour House Inn
Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
  • cleanliness
    Cozy Cheshire B&B within easy reach of Adams Theater and Mount Greylock.
The price is $254
$268 total
includes taxes & fees
Mar 24 - Mar 25
Harbour House Inn
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 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
Sunset Inn
Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
  • cleanliness
    Countryside lodging with a seasonal pool, steps away from Tanglewood Music Center.
The price is $95
$106 total
includes taxes & fees
Mar 24 - Mar 25
Sunset Inn
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (814 reviews)
  • cleanliness
    Restful sanctuary in Pittsfield with free WiFi and parking, perfect for skiers.
The price is $79
$88 total
includes taxes & fees
Apr 1 - Apr 2
FairBridge Inn Express
Chambery Inn
Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
  • cleanliness
    Peaceful countryside retreat with spa treatments just minutes from Tanglewood Music Center.
The price is $190
$212 total
includes taxes & fees
Mar 24 - Mar 25
Chambery Inn
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 5 - Apr 6
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
  • cleanliness
    Step back from the crowds with a relaxing Berkshires escape next to scenic fairways.
The price is $329
$367 total
includes taxes & fees
Mar 24 - Mar 25
Devonfield Inn B&B
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, (1,001 reviews)
  • cleanliness
    Tranquil lakefront escape with stunning sunset views and a 24-hour fitness center.
The price is $95
$106 total
includes taxes & fees
Apr 13 - Apr 14
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (855 reviews)
  • cleanliness
    Berkshire getaway offers indoor and outdoor pools with mountain scenery and cafe.
The price is $113
$145 total
includes taxes & fees
Mar 25 - Mar 26
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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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Frequently asked questions

What accommodations do travelers like in Windsor?
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.