Windsor Hotels from ₹6,276

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
12 Sept - 14 Sept
Next weekend
19 Sept - 21 Sept

Filter by

Guest rating
Guest rating
Star rating

Top 10 Windsor hotels and places to stay

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₹10,879
₹12,151 total
includes taxes & fees
18 Sept - 19 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Good location, lovely grounds, we enjoyed the pool"
The price is ₹10,428
₹11,648 total
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (715)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ₹14,179
₹15,838 total
includes taxes & fees
10 Sept - 11 Sept
Berkshires Untold
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ₹11,270
₹16,039 total
includes taxes & fees
10 Sept - 11 Sept
The Cornell Inn, Lenox & The Berkshires
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1005)
"Great location!"
The price is ₹13,425
₹14,996 total
includes taxes & fees
11 Sept - 12 Sept
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (623)
"The perfect place "
The price is ₹13,437
₹16,981 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1995)
"All around loved everything about the place! "
The price is ₹7,667
₹9,533 total
includes taxes & fees
21 Sept - 22 Sept
Vacation Village in the Berkshires
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (541)
"Great place , love it, will return"
The price is ₹13,484
₹15,061 total
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (36)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is ₹12,494
₹13,955 total
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (719)
"Pleasant stay"
The price is ₹10,247
₹12,679 total
includes taxes & fees
16 Sept - 17 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Wonderful old inn; chock full of charm."
The price is ₹14,022
₹19,607 total
includes taxes & fees
10 Sept - 11 Sept
The Red Lion Inn
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ₹8,650
₹9,662 total
includes taxes & fees
11 Sept - 12 Sept
Huttopia Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (870)
"Consistently a clean room with welcoming staff."
The price is ₹9,621
₹10,746 total
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (770)
"Hotel on North punches above its weight. It's a great hotel in an OK downtown. "
The price is ₹14,034
₹15,676 total
includes taxes & fees
28 Sept - 29 Sept
Hotel On North
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (293)
"This motel is a good value considering the location and condition. Simple motel that is fairly dated. Very friendly owners/staff. If you are looking for a basic motel that is not expensive, is clean and convenient to Williamstown, this a good fit."
The price is ₹7,699
₹8,599 total
includes taxes & fees
11 Sept - 12 Sept
Williamstown Motel
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.6 out of 10, (875)
"A good location. Easy to find and access. Very clean and modern. "
The price is ₹9,708
₹10,844 total
includes taxes & fees
11 Sept - 12 Sept
Howard Johnson by Wyndham Williamstown
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1003)
"Very nice stay"
The price is ₹9,377
₹10,474 total
includes taxes & fees
14 Sept - 15 Sept
Best Western Plus Berkshire Hills Inn & Suites
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (735)
"This was an easy, clean and quiet motel not too far from North Adams. I think it would be great for hikers or others seeking a pleasant place to stop. Really nice tables and sit-down swings for adults, too. "
The price is ₹7,855
₹8,774 total
includes taxes & fees
10 Sept - 11 Sept
The Villager Motel
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (779)
"Close to our target event a plus"
The price is ₹6,276
₹7,010 total
includes taxes & fees
23 Sept - 24 Sept
FairBridge Inn Express
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (631)
"This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area."
The price is ₹5,600
₹6,256 total
includes taxes & fees
22 Sept - 23 Sept
Econo Lodge Lee - Great Barrington
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

More cheap stays in Windsor

More cheap stays in Windsor

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA
The price is ₹6,276 per night from 23 Sept to 24 Sept
₹6,276
₹7,010 total
23 Sept - 24 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Berkshire Mountain Lodge. See all available top hotels, or 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 Mount Greylock State Reservation Visitor Center, Mount Greylock and Barrington Stage Company. You'll also find Berkshire Museum and Colonial Theater 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.