Windsor hotels from HK$596

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25 Dec - 26 Dec
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26 Dec - 27 Dec
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26 Dec - 28 Dec
Next weekend
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Our top choices for Windsor hotels

Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn PLUS+ South Deerfield – Amherst

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, (1001)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is HK$665
HK$743 total
includes taxes & fees
8 Jan - 9 Jan 2026
Red Roof Inn PLUS+ South Deerfield – Amherst
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is HK$594
HK$663 total
includes taxes & fees
8 Jan - 9 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is HK$616
HK$1,069 total
includes taxes & fees
4 Jan - 5 Jan 2026
Blooming Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is HK$721
HK$805 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is HK$780
HK$871 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is HK$686
HK$766 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
The price is HK$553
HK$654 total
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Corner Motel
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is HK$972
HK$1,085 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1000)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is HK$643
HK$718 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South
In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is HK$1,389
HK$1,468 total
includes taxes & fees
28 Dec - 29 Dec
Blue Vista Motor Lodge
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is HK$1,050
HK$1,173 total
includes taxes & fees
8 Jan - 9 Jan 2026
Element Lenox Berkshires
Exterior
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (767)
"It's very good for stay over"
United States
Frances
The price is HK$537
HK$599 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Villager Motel
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is HK$994
HK$1,111 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"Old time charm and hot tub under the stars"
United States
Lori
The price is HK$1,120
HK$1,599 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is HK$803
HK$897 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is HK$614
HK$686 total
includes taxes & fees
31 Dec - 1 Jan 2026
Howard Johnson by Wyndham Lenox
Exterior
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (996)
"Very friendly staff and fresh fruit at breakfast!"
United States
Justin
The price is HK$595
HK$664 total
includes taxes & fees
1 Jan - 2 Jan 2026
Willows Motel Williamstown
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (591)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is HK$770
HK$860 total
includes taxes & fees
8 Jan - 9 Jan 2026
Maple Terrace Motel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
The price is HK$829
HK$910 total
includes taxes & fees
5 Jan - 6 Jan 2026
Shaker Mill Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is HK$767
HK$1,031 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain 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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Top Windsor Hotel Reviews

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

10/10 Excellent
"Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more."
Cynthia 2-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is HK$614 per night from 31 Dec to 1 Jan
HK$614
HK$686 total
31 Dec - 1 Jan 2026
includes taxes & fees
7.4/10 Good! (827 reviews)

Hotels in Windsor with star-rating

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Hotel Downstreet, an Ascend Collection Hotel and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.
What are some of the best holiday rentals that Windsor has to offer?
Peace and quiet on the lake: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
What is staying in Windsor like?
Visitors can enjoy all that Windsor has to offer, including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodation options to choose from. Find out more about Windsor.
What should I do while I'm visiting Windsor?
Places to visit in the wider area include Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center and Swift River. You'll also find Mount Greylock and Barrington Stage Company in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.
What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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