Hotels in Windsor

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Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9

Where to stay in Windsor?

Desk, iron/ironing board, WiFi (free), bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (859 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $69
$77 total
includes taxes & fees
Jul 28 - Jul 29
FairBridge Inn Express
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,023 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $170
$190 total
includes taxes & fees
Jul 27 - Jul 28
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

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, (1,006 reviews)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is $118
$132 total
includes taxes & fees
Jul 29 - Jul 30
Best Western Plus Berkshire Hills Inn & Suites
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, WiFi (free), bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (262 reviews)
The price is $86
$96 total
includes taxes & fees
Aug 2 - Aug 3
Rodeway Inn
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, (36 reviews)
Wake up to a complimentary self-serve breakfast at this charming Adams guesthouse. Enjoy free WiFi and parking while exploring nearby Adams Theater and Berkshire Scenic Railway Museum. Just a 22-minute drive from Pittsfield Station.
The price is $166
$185 total
includes taxes & fees
Jul 27 - Jul 28
The Revival House
Reception

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, (1,004 reviews)
This hotel puts you close to Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy clean rooms with free WiFi and parking, plus attentive 24-hour staff to assist throughout your stay. UMass Amherst is just a short drive away.
The price is $99
$110 total
includes taxes & fees
Jul 30 - Jul 31
Red Roof Inn PLUS+ South Deerfield – Amherst
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,025 reviews)
The price is $122
$158 total
includes taxes & fees
Aug 25 - Aug 26
Berkshire Mountain Lodge
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (142 reviews)
Immerse yourself in the tranquility of Shelburne Falls at this welcoming guesthouse. Free WiFi and daily housekeeping provide essential comforts, while snowmobiling, snowshoeing, and sledding await right outside. Popular attractions like Glacial Potholes are nearby.
The price is $111
$173 total
includes taxes & fees
Aug 17 - Aug 18
Blooming Inn
Desk, iron/ironing board, WiFi (free), bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (897 reviews)
Enjoy a serene retreat in Pittsfield with a seasonal outdoor pool and proximity to Colonial Theater and Berkshire Museum. This motel offers clean rooms, free WiFi, and parking. Just a 2-minute drive from the transportation hub for your Tanglewood adventures.
The price is $90
$101 total
includes taxes & fees
Jul 27 - Jul 28
Berkshire Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,005 reviews)
Unwind at this centrally located Pittsfield hotel with an indoor pool and health club. Just 15 minutes from Tanglewood Music Center and a quick 6-minute walk to transportation. Enjoy quiet rooms with microwaves, refrigerators, and a bar on-site.
The price is $114
$127 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (890 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $99
$111 total
includes taxes & fees
Jul 27 - Jul 28
Howard Johnson by Wyndham Lenox
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, (152 reviews)
The price is $190
$212 total
includes taxes & fees
Jul 27 - Jul 28
The Trail in Adams - Berkshires’ Art Hotel
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (934 reviews)
The price is $95
$111 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Corner Motel
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
This charming B&B offers free breakfast, WiFi, and parking in scenic Cheshire. Explore nearby attractions like Adams Theater and Mount Greylock State Reservation, then return to this welcoming inn. Pittsfield Station is just a 16-minute drive away.
The price is $254
$268 total
includes taxes & fees
Jul 28 - Jul 29
Harbour House Inn
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (110 reviews)
Tucked in New Ashford, this welcoming motel provides a refreshing seasonal outdoor pool, terraced grounds, and garden spaces. Just 15 minutes from skiing at Jiminy Peak and Brodie Mountain with free WiFi and convenient parking.
The price is $141
$154 total
includes taxes & fees
Jul 27 - Jul 28
The Springs Motel
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (380 reviews)
The price is $104
$116 total
includes taxes & fees
Jul 28 - Jul 29
The Central Downtown Inn & Suites
Front of property

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 $161
$179 total
includes taxes & fees
Aug 16 - Aug 17
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (145 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is $156
$174 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
The price is $127
$142 total
includes taxes & fees
Aug 24 - Aug 25
Quality Inn Lee - Lenox South
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 Yankee Inn

The Yankee Inn

8/10 Good
"Very clean lobby, breakfast area and our room. Comfortable bed and hotel was very accommodating in changing our initial room assignment based on my request for a first floor room. my husband has a disability. One constructive suggestion: air conditioning unit in our room was somewhat noisy though room was comfortably cool. Also housekeeping did not replace coffee mugs that we had used; they needed to be cleaned or swapped out for clean ones. Nice variety of breakfast foods and we had all that we needed. Fresh fruit was delicious appreciated. Overall we would definitely stay here again."
Mary 2-night trip
Posted 2 hours ago
The Yankee Inn

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.