Hotels in Windsor

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Check prices for these dates

This weekend
17 July - 19 July
Next weekend
24 July - 26 July

Where to stay in Windsor?

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Windsor on Hotels.com. These Windsor hotels consistently deliver on comfort, location and traveller experience. Last updated on .

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 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 AU$243
includes taxes & fees
15 July - 16 July
The Yankee Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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 Centre nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness centre. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is AU$191
includes taxes & fees
15 July - 16 July
Best Western Plus Berkshire Hills Inn & Suites
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, (133 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing spa pool after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is AU$228
includes taxes & fees
16 July - 17 July
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (491 reviews)
The price is AU$109
includes taxes & fees
15 July - 16 July
Berkshire Travel Lodge
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
The price is AU$304
includes taxes & fees
10 Aug - 11 Aug
Berkshire Lake Lodge
BBQ/picnic Area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (17 reviews)
The price is AU$213
includes taxes & fees
15 July - 16 July
Hideaway Inn Lenox
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (928 reviews)
The price is AU$149
includes taxes & fees
19 July - 20 July
Cozy Corner Motel
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (800 reviews)
Wake up to continental breakfast at this friendly motel near the Mountain Meadow Preserve. Clean, comfortable rooms with free WiFi await after a day of hiking nearby trails. The helpful staff will ensure a memorable stay in Williamstown.
The price is AU$159
includes taxes & fees
15 July - 16 July
The Villager Motel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (141 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 AU$273
includes taxes & fees
15 July - 16 July
Blooming Inn
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, (151 reviews)
The price is AU$337
includes taxes & fees
15 July - 16 July
The Trail in Adams - Berkshires’ Art Hotel
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.
The price is AU$293
includes taxes & fees
20 July - 21 July
Shaker Mill Inn
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, (883 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 AU$159
includes taxes & fees
15 July - 16 July
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (852 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 AU$96
includes taxes & fees
27 July - 28 July
FairBridge Inn Express
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,009 reviews)
Immerse in the Berkshire charm at this Williamstown motel featuring an outdoor pool with pool bar. Rooms offer refrigerators and microwaves for convenience, while free breakfast, WiFi, and parking enhance your visit. Nearby Colonial Plaza awaits exploration.
The price is AU$151
includes taxes & fees
15 July - 16 July
Willows Motel Williamstown
Standard Room, 1 King Bed, Non Smoking

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (257 reviews)
The price is AU$129
includes taxes & fees
20 July - 21 July
Rodeway Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,013 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 AU$212
includes taxes & fees
19 July - 20 July
Quality Inn Lee - Lenox South
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, (1,011 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 AU$159
includes taxes & fees
19 July - 20 July
Red Roof Inn PLUS+ South Deerfield – Amherst
View from property

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (331 reviews)
The price is AU$154
includes taxes & fees
15 July - 16 July
Williamstown Motel
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

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

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

10/10 Excellent
"Very nice and clean hotel for an overnight stay passing through Massachusetts. Located off a very busy road so pulling out of the parking lot can be difficult."
Timothy 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

How much does a hotel room cost in Windsor?
You can discover great hotels in Windsor from AU$129 with properties to suit all budgets and needs. If you're after an affordable hotel in Windsor that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Windsor hotels?
Discover great deals on Windsor hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Windsor hotels.
Can I book Windsor hotels with free cancellation?
To book a refundable Windsor hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
Can I book a refundable accommodation option in Windsor?
If you want the flexibility to change your plans to Windsor, most hotels offer refundable* rates that you can book. You can see this accommodation 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 visit?
July and August are typically the warmest months in Windsor, when the average temperature is 17°C. January and February are the coldest months, when the average temperature is -4°C. 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, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.

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