Find 4 Star Hotels in Windsor, MA from $114

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Check availability on Windsor 4 Star Hotels

Tonight
Oct 28 - Oct 29
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Oct 29 - Oct 30
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Compare Windsor 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Front of property - evening/night
The Williams Inn
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (529)
"Nice place to stay for a wedding "
United States
Timothy
$197 nightly
The price is $220
Nov 17 - Nov 18
Total with taxes and fees
The Williams Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (333)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
$102 nightly
The price is $114
Nov 2 - Nov 3
Total with taxes and fees
The Central Downtown Inn & Suites
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
$191 nightly
The price is $213
Nov 2 - Nov 3
Total with taxes and fees
Lakehouse Inn
Business center
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
9.2 out of 10, Wonderful, (109)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$335 nightly
The price is $374
Nov 11 - Nov 12
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Seven Hills Inn
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Exterior
General Williams Estate House Lenox/Stockbridge
General Williams Estate House Lenox/Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
United States
Joanna T.
General Williams Estate House Lenox/Stockbridge
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$369 nightly
The price is $412
Nov 21 - Nov 22
Total with taxes and fees
Devonfield Inn B&B
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
$364 nightly
The price is $407
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Stockbridge
Exterior
Hampton Terrace Inn
Hampton Terrace Inn
4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
$307 nightly
The price is $343
Nov 2 - Nov 3
Total with taxes and fees
Hampton Terrace Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
33 Main
4.0 star property
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$445 nightly
The price is $498
Nov 25 - Nov 26
Total with taxes and fees
33 Main
Front of property - evening/night
Garden Gables Inn
Garden Gables Inn
4.0 star property
9.2 out of 10, Wonderful, (57)
"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
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Top Windsor Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Lovely property, friendly, helpful staff. Modern, large rooms. Pretty decor."
michelle 2-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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