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Aug 4 - Aug 5
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Top 10 trending Windsor hotels

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Loved the Yankee Inn!"
The price is P8,850
P9,885 total
includes taxes & fees
Aug 17 - Aug 18
The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (507)
"Property was excellent "
The price is P9,348
P10,442 total
includes taxes & fees
Sep 2 - Sep 3
The Constance by the Lenox Collection
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, (1000)
"Beautiful location!"
The price is P7,366
P8,228 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1005)
"Clean,friendly staff and great location."
The price is P8,355
P9,333 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Downstreet, Ascend Hotel Collection
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (658)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is P24,669
P27,556 total
includes taxes & fees
Aug 8 - Aug 9
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, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P7,752
P10,933 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1930)
"Great stay with all plenty of things to do…"
The price is P5,456
P6,732 total
includes taxes & fees
Aug 19 - Aug 20
Vacation Village in the 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, (845)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is P6,689
P7,471 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (761)
"Close to our target event a plus"
The price is P4,135
P4,619 total
includes taxes & fees
Aug 17 - Aug 18
FairBridge Inn Express
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, (683)
"Had a great time"
The price is P6,933
P8,556 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1001)
"Very nice stay"
The price is P6,921
P7,731 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Food was great!"
The price is P10,993
P14,878 total
includes taxes & fees
Aug 6 - Aug 7
The Red Lion Inn
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (618)
"It was a clean, well-run, low cost option. "
The price is P3,708
P4,142 total
includes taxes & fees
Aug 17 - Aug 18
Econo Lodge Lee - Great Barrington
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (282)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is P5,182
P5,789 total
includes taxes & fees
Sep 2 - Sep 3
Williamstown Motel
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (431)
"Beautiful scenery. Room was not fancy but comfortable and clean. "
The price is P3,978
P4,297 total
includes taxes & fees
Aug 5 - Aug 6
Berkshire Travel Lodge
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (860)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is P6,397
P7,146 total
includes taxes & fees
Aug 5 - Aug 6
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (725)
"Great quiet stay. "
The price is P5,177
P5,782 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (554)
"Very clean and very nice staff. Breakfast was great"
The price is P9,684
P10,817 total
includes taxes & fees
Aug 6 - Aug 7
Berkshire Valley Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (540)
"Excellent stay!"
Berkshire Mountain Lodge
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1001)
"Quiet and nice stay. Wish the area had better bus service ."
The price is P6,229
P6,958 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn PLUS+ South Deerfield – Amherst
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 food and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Food was great!"
Emily 1-night trip
Posted 3 days ago
The Red Lion Inn

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 traveler data. Other good options for your visit to the area are Hotel Downstreet, Ascend Hotel Collection and Red Roof Inn PLUS+ South Deerfield – Amherst. 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! Most hotel bookings are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

Where can I learn more about changing or cancelling my trip to Windsor?

For more information about updating your trip to Windsor or cancelling it, click here.

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 with an onsite pool. View all hotels with pools in Windsor.

What's the best hotel for staying near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations 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. Check out what more to see and do in Expedia's Windsor guide.

What's the seasonal weather like in Windsor?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.