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Find 4 Star Hotels in Windsor, MA from $111

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Check availability on Windsor 4 Star Hotels

Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

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 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.
An outdoor seating area with stone fire pit, chairs, and a red building in the background.

1. The Williams Inn

The Williams Inn
Williamstown
United States
John
$255 nightly
$285 total
Sep 14 - Sep 15
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 compact living space with a kitchenette, a dining area, and a sofa.
A modern apartment with a living room, kitchenette, and dining area.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
$99 nightly
$111 total
Aug 25 - Aug 26
Total with taxes and fees
The Central Downtown Inn & Suites
A living room with a fireplace, leather sofas, and a dog.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A stone fountain surrounded by trees in a park setting.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United Kingdom
Michele
$396 nightly
$442 total
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
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
$358 nightly
$399 total
Sep 7 - Sep 8
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 room with a large bay window, a wooden bench with cushions, and a chandelier.
A row of turquoise bicycles parked in front of a building with brown-framed windows and a white facade.
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 modern bathroom with a glass shower, white marble walls, and a large window.
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.
A room with a large bed, a chair, and a decorative hanging light fixture.

6. 33 Main

33 Main
Lenox
United States
Tatyana
$700 nightly
$781 total
Aug 31 - Sep 1
Total with taxes and fees
33 Main
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 dining room with a large table set for a meal, surrounded by ornate chairs.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.

7. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
$233 nightly
$260 total
Sep 21 - Sep 22
Total with taxes and fees
Hampton Terrace Inn
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.

8. Lakehouse Inn

Lakehouse Inn
Lee
United States
Angela
Lakehouse Inn
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
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.

9. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Richard
$389 nightly
$435 total
Sep 3 - Sep 4
Total with taxes and fees
Devonfield Inn B&B
A deck with outdoor furniture, a hot tub, and a grill.
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.
A kitchen with wooden cabinets, a stainless steel refrigerator, a window with a view of greenery, and a countertop with various items.

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
"Staff and stay were excellent. Room was spotless."
Laura 2-night trip
Posted 3 hours 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 $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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