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Our top choices for Windsor 3-star hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,233 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Feb 22 - Feb 23
Total with taxes and fees
Vacation Village in the Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (835 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$121 nightly
The price is $136
Mar 11 - Mar 12
Total with taxes and fees
Berkshire Mountain Lodge

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,004 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
$102 nightly
The price is $114
Mar 7 - Mar 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (854 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
$98 nightly
The price is $110
Mar 8 - Mar 9
Total with taxes and fees
Berkshires Untold

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (833 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
$130 nightly
The price is $145
Feb 22 - Feb 23
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,001 reviews)
"Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel."
United States
Kelly
$126 nightly
The price is $140
Feb 24 - Feb 25
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
$185 nightly
The price is $207
Mar 10 - Mar 11
Total with taxes and fees
The Red Lion Inn

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (822 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
$140 nightly
The price is $156
Feb 25 - Feb 26
Total with taxes and fees
Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,004 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
$98 nightly
The price is $109
Mar 2 - Mar 3
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (599 reviews)
"Our stay was great! "
United States
Gianna
$130 nightly
The price is $145
Mar 1 - Mar 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (455 reviews)
"The great people!!!"
United States
Julie
$164 nightly
The price is $183
Mar 11 - Mar 12
Total with taxes and fees
The Porches Inn at Mass MoCA

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$189 nightly
The price is $211
Mar 8 - Mar 9
Total with taxes and fees
Jiminy Peak Mountain Resort

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
$137 nightly
The price is $154
Feb 10 - Feb 11
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (666 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
$136 nightly
The price is $152
Mar 8 - Mar 9
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Feb 22 - Feb 23
Total with taxes and fees
Element Lenox Berkshires

The Ponds at Foxhollow

The Ponds at Foxhollow
3.0 star property
Lenox
8.6 out of 10, Excellent, (140 reviews)
"Great place"
United States
Lisa
The Ponds at Foxhollow

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
$139 nightly
The price is $150
Mar 3 - Mar 4
Total with taxes and fees
Blooming Inn

Apple Tree Inn

Apple Tree Inn
3.0 star property
Lenox
8.6 out of 10, Excellent, (316 reviews)
"Great inn, good food at the restaurant!"
United States
michael
Apple Tree Inn

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook
3.0 star property
Hancock
9.2 out of 10, Wonderful, (569 reviews)
"Good place to take your family."
United States
Maria
Club Wyndham Bentley Brook

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very Good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
United States
Miguel
$167 nightly
The price is $186
Feb 16 - Feb 17
Total with taxes and fees
Gateways Inn & Restaurant
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Explore similar 4-star hotels

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Top Windsor Hotel Reviews

Find out more about Windsor

Three Star Hotel Guide for Windsor

There’s a reason the top 3 star hotels in Windsor, Massachusetts are so incredibly popular: They combine comforting amenities and just-for-you service with some of the best rates and discounts the area has to offer. When you book a stay at a three star hotel in Windsor, you’ll get access to perfect little perks like on-site restaurants and cocktail bars, well-appointed fitness centers, and spacious rooms.

Search for a cheap deal on a 3 star upscale hotel in Windsor for the most elegant experience, or grab a low rate on one of the cheap 3 star hotels in Windsor near the local attractions, if you want something a touch more unassuming. Whatever your traveling style, make sure to use the search tools at Expedia to track down prices, read more about amenities, and score a few local discounts.

From business trips to family getaways, the Windsor 3 star hotels offer a fantastic home base for any type of vacation.

Frequently asked questions

How much does it cost to stay in a 3-star hotel in Windsor?
Find the perfect trifecta of comfort, affordability and quality at a 3-star hotel in Windsor with our handy filters. Enter your travel dates and then tailor your search based on the amount you want to spend per night.

  • Search for the lowest price per night right now from $122

What is the difference between a 4-star and 3-star hotel in Windsor?
Relaxation comes easy in 3-star hotels in Windsor. On top of cozy surroundings, these more cost-effective properties include a variety of welcome amenities like WiFi, coffee maker and a gym. A 4-star hotel offers a classier experience with enhanced features such as an on-site spa center, pool and more spacious rooms. Regardless of your preferred hotel style or what you want to spend, we have the right option for you.
What is the difference between a 3-star hotel and a motel in Windsor?
Motels usually offer more affordable rates than hotels, which makes them excellent if you're exploring around Windsor and sticking to a budget. A great option for overnight stays, these roadside getaways have simply furnished rooms, basic services and ample parking. Choose a 3-star hotel and you can expect to pay more for additional comfort, privacy and amenities. Travelers can make use of things like a gym, free WiFi and business services at this property type.

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