Hotels in Windsor

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

Where to stay in Windsor?

A building entrance with a large planter with purple flowers and a small tree.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (972 reviews)
This boutique hotel combines business-friendly amenities with cozy accommodations near Barrington Stage Company. Enjoy thoughtful perks including complimentary WiFi, free parking, and convenient room service, all while exploring nearby cultural attractions.
The price is $116
$130 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

2. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (931 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 $71
$79 total
includes taxes & fees
Nov 2 - Nov 3
FairBridge Inn Express
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

3. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (283 reviews)
The price is $67
$75 total
includes taxes & fees
Nov 29 - Nov 30
Rodeway Inn
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 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 $115
$128 total
includes taxes & fees
Nov 20 - Nov 21
The Yankee Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

5. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (158 reviews)
The price is $174
$194 total
includes taxes & fees
Nov 2 - Nov 3
The Trail in Adams - Berkshires’ Art Hotel
A living room with a fireplace, two sofas, and four black side tables.

6. The Revival House

The Revival House
3.0 star property
Adams
8.8 out of 10, Excellent, (43 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 $138
$154 total
includes taxes & fees
Nov 9 - Nov 10
The Revival House
A patio area with outdoor furniture, a fire pit, and potted plants.

7. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (123 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 $107
$117 total
includes taxes & fees
Nov 4 - Nov 5
The Springs Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

8. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 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 $83
$92 total
includes taxes & fees
Nov 28 - Nov 29
Berkshire Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
Dive into the indoor pool at this Lenox hotel, just 10 minutes from Tanglewood Music Center. Enjoy a complimentary breakfast before exploring nearby attractions like Guido's Marketplace and Bousquet Ski Area. Free WiFi and parking complete your comfortable stay.
The price is $110
$122 total
includes taxes & fees
Nov 7 - Nov 8
Hampton Inn & Suites Berkshires-Lenox
Exterior

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,250 reviews)
The price is $95
$128 total
includes taxes & fees
Nov 8 - Nov 9
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (252 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 $103
$115 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

12. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (933 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 $79
$88 total
includes taxes & fees
Nov 2 - Nov 3
Howard Johnson by Wyndham Lenox
Room

13. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,005 reviews)
The price is $119
$133 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Downstreet, an Ascend Collection Hotel
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

14. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (527 reviews)
The price is $169
$211 total
includes taxes & fees
Nov 30 - Dec 1
The Porches Inn at Mass MoCA
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

15. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (433 reviews)
The price is $99
$111 total
includes taxes & fees
Nov 2 - Nov 3
The Central Downtown Inn & Suites
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
Embrace comfort at this Pittsfield retreat with an indoor pool and fitness center. Jae's Asian Fusion restaurant serves three daily meals, while rooms offer convenient refrigerators and microwaves. Guido's Marketplace and literary landmarks await nearby.
The price is $119
$133 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

17. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (683 reviews)
Immerse yourself in the Berkshires at this centrally located hotel with an indoor pool and fitness center. Rooms feature microwaves and refrigerators, while the café and bar provide dining options. Free WiFi, parking, and proximity to Kennedy Park enhance your stay.
The price is $114
$127 total
includes taxes & fees
Nov 29 - Nov 30
Courtyard by Marriott Lenox Berkshires
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

18. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 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
Nov 2 - Nov 3
Harbour House Inn
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

19. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,817 reviews)
The price is $95
$117 total
includes taxes & fees
Nov 2 - Nov 3
Vacation Village in the Berkshires
A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

20. Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (241 reviews)
Blue Vista Motor Lodge offers 2 relaxing hot tubs and a rejuvenating sauna to end your day. Located near Florida Free Public Library, this North Adams motel provides complimentary WiFi and parking, with guests praising the helpful staff and clean rooms.
The price is $182
$192 total
includes taxes & fees
Nov 2 - Nov 3
Blue Vista Motor Lodge
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 Williams Inn

The Williams Inn

10/10 Excellent
"Incredible staff, wonderful accommodations, food in restaurant was excellent and they fit us in for a busy Friday night dinner when they didn’t really have room. Great fitness center. Right in the heart of Williamstown / Williams College. Beautiful place!"
Anne 2-night trip
Posted 4 hours ago
The Williams 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.