Find hotels in Windsor, MA from £59

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Filter by

Guest rating
Guest rating
Property class

Top 10 Windsor hotels and places to stay

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

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1004)
"It’s the only place close to the Treehouse so we stayed there, it is definitely a RR Inn."
The price is £88
includes taxes & fees
4 Sept - 5 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (731)
"Great quiet stay. "
The price is £74
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (941)
"Comfortable, clean, and great continental breakfast options! "
The price is £74
includes taxes & fees
2 Sept - 3 Sept
Willows Motel Williamstown
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is £65
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (848)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is £82
includes taxes & fees
2 Sept - 3 Sept
Cozy Corner Motel
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (624)
"Convenient location for my trip"
The price is £57
includes taxes & fees
27 Aug - 28 Aug
Wagon Wheel Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Very comfortable and a nice breakfast "
The price is £91
includes taxes & fees
8 Sept - 9 Sept
Quality Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is £107
includes taxes & fees
9 Sept - 10 Sept
Blooming Inn
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great staff! Comfortable bed! "
The price is £119
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Berkshires-Lenox
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1006)
"Wonderful place to stay"
The price is £103
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
The Porches Inn at Mass MoCA
Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (413)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is £164
includes taxes & fees
24 Sept - 25 Sept
The Porches Inn at Mass MoCA
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 clean rooms and excellent staff."
The price is £88
includes taxes & fees
2 Sept - 3 Sept
Best Western Plus Berkshire Hills Inn & Suites
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (803)
"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room, "
The price is £66
includes taxes & fees
27 Aug - 28 Aug
Berkshire Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

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 £105
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (869)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is £91
includes taxes & fees
2 Sept - 3 Sept
Howard Johnson by Wyndham Williamstown
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1008)
"Great location!"
The price is £119
includes taxes & fees
24 Sept - 25 Sept
Hotel Downstreet, Ascend Hotel Collection
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, (626)
"It was lovely!"
The price is £53
includes taxes & fees
18 Sept - 19 Sept
Econo Lodge Lee - Great Barrington
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, (1002)
"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 £134
includes taxes & fees
4 Sept - 5 Sept
The Cornell Inn, Lenox & The Berkshires
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is £69
includes taxes & fees
7 Sept - 8 Sept
Williamstown Motel
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (180)
"Clean, beautiful view wonderful service"
The price is £170
includes taxes & fees
27 Aug - 28 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Windsor

Explore Windsor: its dining and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Beautiful atmosphere and grounds."
Betsy 2-night trip
Posted 14 hours ago
The Williams Inn

More cheap stays in Windsor

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is £65 per night from 1 Sept to 2 Sept
£65
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (785 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Windsor hotel for you.
How can I save on a Windsor hotel booking with Expedia?
Before booking your Windsor hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.
How much is the nightly rate at a Windsor hotel?
Prices for hotels in Windsor often vary, but you can find a great deal from £59 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.