Find 4 Star Hotels in Windsor, MA from $114

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Check availability on Windsor 4 Star Hotels

Tonight
Mar 29 - Mar 30
Tomorrow
Mar 30 - Mar 31
Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12

Our top choices for Windsor 4-star hotels

Front of property - evening/night

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (601 reviews)
"Amazing place to stay."
United States
Augusta
$179 nightly
The price is $200
Mar 30 - Mar 31
Total with taxes and fees
The Williams Inn
50-inch flat-screen TV with cable channels, TV, streaming services

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (359 reviews)
"Clean room, easy checkin, loved the tea kettle. Clean, comfortable, would definitely return. "
United States
TIFFANY
$102 nightly
The price is $114
Mar 30 - Mar 31
Total with taxes and fees
The Central Downtown Inn & Suites
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
$151 nightly
The price is $169
Apr 3 - Apr 4
Total with taxes and fees
Lakehouse Inn
Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$335 nightly
The price is $374
Apr 13 - Apr 14
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$329 nightly
The price is $367
Mar 30 - Mar 31
Total with taxes and fees
Devonfield Inn B&B
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
$238 nightly
The price is $266
Apr 3 - Apr 4
Total with taxes and fees
The Inn at Stockbridge
Front of property

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467 reviews)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Exterior

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$445 nightly
The price is $498
Apr 6 - Apr 7
Total with taxes and fees
33 Main
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
$252 nightly
The price is $281
Mar 31 - Apr 1
Total with taxes and fees
Hampton Terrace Inn
Front of property - evening/night

Garden Gables Inn

Garden Gables Inn
4.0 star property
Lenox
9.2 out of 10, Wonderful, (57 reviews)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
United States
john
Garden Gables Inn
Apartment (4 Bedrooms) | Interior

Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes!
4.0 star property
Hancock
Family-friendly Hancock Home: Walk to Slopes!
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Top Windsor Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"The hotel is a great, upscale business hotel with friendly staff and a great restaurant."
Julie 1-night trip
Posted 3 days ago
The Williams Inn

Find out more about Windsor

Windsor Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Windsor, Massachusetts are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Windsor 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Windsor. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Windsor, Massachusetts, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Windsor hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
With Expedia's search and sort filters, bagging a top deal on a 4-star hotel in Windsor just got easier. Start by keying in your chosen travel dates and length of your vacation. Then list the results by price and pick a hotel that best fits your style and budget.

  • Search for the lowest price from $114

What's the difference between 5-star and 4-star hotels in Windsor?
If you choose to vacation at a 4-star hotel in Windsor, you'll typically find lots of amenities to ensure you're comfortable, such as a pool, gym and restaurant. You can look forward to high-quality service and deluxe accommodations. Go for a 5-star hotel and you'll have access to a few more perks — think around-the-clock concierge, on-site spas and indulgent turndown services. You'll most likely get additional amenities and first-rate services at a 5-star stay, though both are terrific options for luxury travelers.
Does Windsor have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your next dream getaway in Windsor where everything is taken care of, from your room to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this popular destination.

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