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4 Stars Hotels in Windsor, Massachusetts from CA $156

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Check availability on Windsor 4 Star Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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.
A spacious living area with a fireplace, wooden beams, and a large window.
A bar area with wooden beams, red chairs, and a long wooden table.
A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

1. The Williams Inn

The Williams Inn
Williamstown
United States
William
CA $292
CA $326 total
includes taxes & fees
Oct 18 - Oct 19
The Williams Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
CA $140
CA $156 total
includes taxes & fees
Oct 1 - Oct 2
The Central Downtown Inn & Suites
Front of property
A living room with a fireplace, leather sofas, and a dog.
Exterior
A stone fountain surrounded by trees in a park setting.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United States
Jodi
CA $619
CA $726 total
includes taxes & fees
Oct 1 - Oct 2
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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
CA $730
CA $884 total
includes taxes & fees
Oct 18 - Oct 19
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 large, white, multi-story house with a symmetrical design, surrounded by lush greenery and trees.

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 house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
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
CA $580
CA $648 total
includes taxes & fees
Oct 25 - Oct 26
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 room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A dining room with a large table set for a meal, surrounded by ornate chairs.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
CA $363
CA $406 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Terrace Inn
A modern bathroom with a glass shower, white marble walls, and a large window.
A two-story white house with a front porch, a central entrance, and a small tower-like structure on the roof.
A neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.
A breakfast buffet with pastries, fruits, and condiments.

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 modern living room with a sofa, a coffee table, and a TV mounted on the wall.
A two-story house with a balcony, a front porch, and a well-maintained lawn.

9. Lakehouse Inn

Lakehouse Inn
Lee
United States
Kathleen
Lakehouse Inn
A deck with outdoor furniture, a hot tub, and a grill.
A spacious living area with a brown leather sectional sofa, a wooden coffee table, and a dining area with wooden chairs and a bar.
A cozy living room with a fireplace, a large window, and a dining area set for six.
A bedroom with a large bed, a nightstand, a painting, and a view of the outside.

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

The Williams Inn

The Williams Inn

10/10 Excellent
"Amazing"
Jermay 1-night trip
Posted 2 hours ago
The Williams Inn

Find out more about Windsor

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windsor are calling your name. Known for providing first-rate service in amazing locations, each of the Windsor 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Windsor. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windsor, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windsor hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Windsor?
With Expedia's handy filter tool, locking in a terrific deal on a 4-star hotel in Windsor just got simpler. Start by entering your chosen travel dates and length of your stay. Then sort the results by price and pick the option that best suits your budget and style.
  • Search for the lowest price from CA $156
What's the difference between 5-star and 4-star hotels in Windsor?
If you decide to book a stay at a 4-star hotel in Windsor, you'll typically find lots of conveniences to keep you relaxed, such as a restaurant, gym and pool. You can look forward to excellent service and upmarket accommodations. Go for a 5-star hotel and you'll get a few more perks — think concierge assistance, on-site spas and nightly turndown services. You'll most likely get extra amenities and premium services at a 5-star getaway, though both are fabulous options for luxury travellers.
Does Windsor have any 4-star all-inclusive resorts?
Finding vacation bliss in Windsor is as easy as entering in your destination and dates, and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your meals, accommodations, entertainment and activities, or choose a standard 4-star resort in or around this top destination.

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