Default HTG hotel image

Find 4 Star Hotels in Windsor, MA from $130

Check availability on Windsor 4 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Windsor 4-star hotels

Front of property - evening/night

1. The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (648 reviews)
"amazing friendly and helpful staff perfect stay!"
United States
Thomas
$243 nightly
The price is $271
Aug 16 - Aug 17
Total with taxes and fees
The Williams Inn
Exterior

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (381 reviews)
"Large, clean, comfortable suite."
United States
Rena
$116 nightly
The price is $130
Aug 2 - Aug 3
Total with taxes and fees
The Central Downtown Inn & Suites
Front of property

3. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Beautifully decorated inside and gorgeous gardens and landscaping outside. A lovely serene spot away from the crowds that are only minutes away in downtown Stockbridge. The breakfasts were plentiful, artfully presented and delicious. Staff were friendly and very competent."
United States
Barbara
$427 nightly
The price is $477
Aug 10 - Aug 11
Total with taxes and fees
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room

4. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Aug 16 - Aug 17
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

5. 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
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

6. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
$666 nightly
The price is $744
Aug 16 - Aug 17
Total with taxes and fees
33 Main
Porch

7. Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (303 reviews)
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
United States
Angela
Lakehouse Inn
Front of property - evening/night

8. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
$409 nightly
The price is $457
Aug 27 - Aug 28
Total with taxes and fees
Devonfield Inn B&B
Exterior detail

9. 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
$279 nightly
The price is $312
Aug 27 - Aug 28
Total with taxes and fees
Hampton Terrace Inn
Apartment (4 Bedrooms) | Front of property

10. 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!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Hotel was terrific..very clean..restaurant was excellent…very well located for Williams College"
GENE 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 $130

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.

Explore a world of travel with Expedia