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Top 10 trending Windsor hotels

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, (1004)
"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 P6,112
P6,828 total
includes taxes & fees
Sep 1 - Sep 2
Red Roof Inn PLUS+ South Deerfield – Amherst
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is P5,884
P9,370 total
includes taxes & fees
Aug 18 - Aug 19
Blooming 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, (1004)
"Lovely setting on the lake."
The price is P7,229
P8,075 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is P5,594
P6,248 total
includes taxes & fees
Sep 1 - Sep 2
Huttopia Berkshires
Willows Motel Williamstown
Exterior

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 P5,086
P5,681 total
includes taxes & fees
Sep 1 - Sep 2
Willows Motel Williamstown
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (680)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is P9,125
P10,193 total
includes taxes & fees
Aug 18 - Aug 19
Berkshires Untold
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great staff! Comfortable bed! "
The price is P8,199
P9,158 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (727)
"Great quiet stay. "
The price is P5,080
P5,674 total
includes taxes & fees
Sep 1 - Sep 2
The Villager Motel
The Revival House
1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.4 out of 10, Exceptional, (10)
"Self check in was easy. Rooms were spacious and clean. Great place."
The price is P10,274
P11,476 total
includes taxes & fees
Aug 18 - Aug 19
The Revival House
The Porches Inn at Mass MoCA
2 bedrooms, Frette Italian sheets, premium bedding, down comforters

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 P10,140
P12,601 total
includes taxes & fees
Sep 15 - Sep 16
The Porches Inn at Mass MoCA
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)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is P7,288
P10,372 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
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, (1004)
"Great location!"
The price is P8,199
P9,158 total
includes taxes & fees
Sep 15 - Sep 16
Hotel Downstreet, Ascend Hotel Collection
Element Lenox Berkshires
Free daily continental breakfast

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is P8,676
P9,691 total
includes taxes & fees
Sep 1 - Sep 2
Element Lenox Berkshires
Cozy Corner Motel
Exterior

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 P5,365
P6,297 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Corner Motel
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (569)
"Fabulous place"
The price is P8,676
P9,691 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (571)
"The staff, room and property was wonderful! "
The price is P6,421
P7,172 total
includes taxes & fees
Sep 2 - Sep 3
Maple Terrace Motel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (571)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (17)
"Really enjoyed my stay here, definitely need a car to get around"
The price is P7,714
P8,616 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Williams Inn
Front of property - evening/night

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 P13,305
P14,861 total
includes taxes & fees
Sep 7 - Sep 8
The Williams Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is P6,258
P6,991 total
includes taxes & fees
Sep 1 - Sep 2
Quality Inn
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

Quality Inn

Quality Inn

10/10 Excellent
"Friendly staff"
Edward 1-night trip
Posted 2 days ago
Quality 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 Berkshire Mountain Lodge and FairBridge Inn Express. 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.