Windsor Hotels

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Top 10 trending Windsor hotels

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"Friendly staff and good place for the price. You get everything you need, is clean and close to dinning/shopping. I recommend it. "
The price is €103
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn PLUS+ South Deerfield – Amherst

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great staff! Comfortable bed! "
The price is €138
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Berkshires-Lenox

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is €138
includes taxes & fees
14 Sept - 15 Sept
Blooming Inn

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (485)
"The property was spacious but still had a cozy feel. "
The price is €224
includes taxes & fees
7 Sept - 8 Sept
The Williams Inn

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (937)
"Great breakfast, clean room, functioning AC and helpfull staff."
The price is €85
includes taxes & fees
1 Sept - 2 Sept
Willows Motel Williamstown

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Wonderful place to stay"
The price is €129
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (844)
"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 €95
includes taxes & fees
3 Sept - 4 Sept
Cozy Corner Motel

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (727)
"Great quiet stay. "
The price is €85
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Very clean rooms and excellent staff."
The price is €114
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Had a wonderful time "
The price is €121
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great location!"
The price is €138
includes taxes & fees
14 Sept - 15 Sept
Hotel Downstreet, Ascend Hotel Collection

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (407)
"Very comfortable room that worked great for our family. "
The price is €190
includes taxes & fees
15 Sept - 16 Sept
The Porches Inn at Mass MoCA

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is €105
includes taxes & fees
1 Sept - 2 Sept
Quality Inn

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (623)
"Convenient location for my trip"
The price is €66
includes taxes & fees
18 Aug - 19 Aug
Wagon Wheel Inn

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (286)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is €85
includes taxes & fees
2 Sept - 3 Sept
Williamstown Motel

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is €155
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (794)
"good location....easy access to highlight destinations and downtown"
The price is €95
includes taxes & fees
18 Aug - 19 Aug
Berkshire Inn

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (753)
"Staff were excellent and welcoming."
Hotel On North

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (56)
"Love this renovated motel. They made it cute and trendy"
The price is €112
includes taxes & fees
9 Sept - 10 Sept
The Springs Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (14)
"Really enjoyed my stay here, definitely need a car to get around"
The price is €145
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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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Learn more about Windsor

Explore Windsor: its dining and more!

Top Windsor Hotel Reviews

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 Berkshire Mountain Lodge and FairBridge Inn Express. See all available top hotels, or vacation rentals in Windsor.

What are some of the best holiday rentals that Windsor has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 are some hotels with pools in Windsor?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are two additional hotels that feature an on-site pool. View all hotels with pools 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.