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Find 4 Star Hotels in Windsor, MA from $111

Check availability on Windsor 4 Star Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Windsor 4-star hotels

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.
A bar area with wooden beams, red chairs, and a long wooden table.

1. The Williams Inn

The Williams Inn
Williamstown
United States
Soleil
$213 nightly
$238 total
Nov 8 - Nov 9
Total with taxes and fees
The Williams Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
$99 nightly
$111 total
Oct 14 - Oct 15
Total with taxes and fees
The Central Downtown Inn & Suites
Front of property
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
Exterior
A living room with a fireplace, leather sofas, and a dog.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

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
Stockbridge
United States
Philippe
$376 nightly
$420 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
An indoor dining area with a central table and chairs, surrounded by a decorative archway and greenery.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.
A room with a large bay window, a wooden bench with cushions, and a chandelier.
A dining room with a large wooden table, blue upholstered chairs, and a chandelier.

5. Seven Hills Inn

Seven Hills Inn
Lenox
United States
Christopher
Seven Hills Inn
A large, two-story house with a well-maintained lawn and a fence.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

6. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A dining room with a large table set for a meal, surrounded by ornate chairs.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
$251 nightly
$280 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
A breakfast buffet with pastries, fruits, and condiments.
A neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.
A room with a large bed, a chair, and a decorative hanging light fixture.

8. 33 Main

33 Main
Lenox
United States
Tatyana
33 Main
A wooden deck with wicker furniture and a view of a lake.
A hallway with wooden flooring, a wooden bench, a vase with flowers, and a mirror on the wall.
A two-story house with a balcony, a front porch, and a well-maintained lawn.
A view of a lakeside property with a deck and a white building.

9. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
A deck with outdoor furniture, a hot tub, and a grill.
A kitchen with wooden cabinets, a stainless steel refrigerator, a window with a view of greenery, and a countertop with various items.
A cozy living room with a fireplace, a large window, and a dining area set for six.
A spacious living area with a brown leather sectional sofa, a wooden coffee table, and a dining area with wooden chairs and a bar.

10. Family-friendly Hancock Home: Walk to Slopes!

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

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 $111
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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