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2 Stars Hotels in Windsor, Massachusetts from CA $99

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Check availability on Windsor 2 Star Hotels

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Windsor 2-star hotels

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A dining area with wooden tables and chairs, a television, and a door with a sign.
A hotel room with a TV, microwave, mini-fridge, desk, chair, mirror, and a coat rack.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.

1. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
Richard
CA $89
CA $99 total
includes taxes & fees
Oct 18 - Oct 19
FairBridge Inn Express
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

2. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $138
CA $154 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with a counter, seating area, and large windows.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A snack bar with shelves of snacks and a refrigerated display.

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ginger
CA $141
CA $157 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

4. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Aleksandr
CA $112
CA $125 total
includes taxes & fees
Oct 18 - Oct 19
Howard Johnson by Wyndham Lenox
A gaming area with arcade machines, a seating area with tables and chairs, and large windows providing natural light.
A hotel room with a television displaying a football game, a desk with a lamp, a microwave, and a refrigerator.
A hotel room with two beds, a desk, a chair, a TV, and a mirror.
A Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.

5. Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
South Deerfield
United States
Jack
CA $127
CA $142 total
includes taxes & fees
Nov 1 - Nov 2
Red Roof Inn PLUS+ South Deerfield – Amherst
A large house with a covered patio area featuring outdoor seating and a fire pit.
A sunlit room with large windows, a stone floor, and two rocking chairs.
A corner dining area with a wooden table set for four, surrounded by upholstered chairs.
A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

6. The Whitlock

The Whitlock
Lenox
United States
Michael
CA $201
CA $225 total
includes taxes & fees
Nov 4 - Nov 5
The Whitlock
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.
A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a television, a microwave, and a sofa.

7. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Lucinda
CA $131
CA $147 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Lee - Lenox South
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

8. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
James
CA $138
CA $155 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Berkshire Hills Inn & Suites
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A room with a blue armchair, a wooden cabinet with a coffee maker, a television on the wall, and a small table with a cup.

9. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
CA $156
CA $174 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Berkshires-Lenox
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.
A hay bale display with pumpkins and scarecrows.

10. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
David
CA $120
CA $134 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.
A residential street with a paved road, a lamp post, and flowering trees.
A motel with a parking lot, a swimming pool, and outdoor seating.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

11. Berkshire Inn

Berkshire Inn
Pittsfield
United States
cheryl
CA $117
CA $131 total
includes taxes & fees
Nov 16 - Nov 17
Berkshire Inn
A building with a covered parking area and a grassy front yard.
A motel with multiple rooms, a parking area, and a large tree in the foreground.
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.
A dining area with wooden chairs and tables, a kitchen counter with appliances, and framed pictures on the wall.

12. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
Williamstown
United States
Barbara
CA $142
CA $159 total
includes taxes & fees
Oct 18 - Oct 19
Howard Johnson by Wyndham Williamstown
Outdoor pool
Front of property
Lobby sitting area
Lobby sitting area

13. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
United States
Kris
CA $96
CA $107 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Travel Lodge
A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.
A cozy room with a round table, a sofa, a leopard-print armchair, and a large window with a view.
A sign for 'Hide Away Inn' with 'Hotel Entrance' below it, set against a snowy landscape with bare trees.
A bedroom with a bed, a fireplace, a staircase, and a TV mounted on the wall.

14. Hideaway Inn Lenox

Hideaway Inn Lenox
Lenox
United States
Barbara
CA $160
CA $179 total
includes taxes & fees
Nov 15 - Nov 16
Hideaway Inn Lenox
A kitchen with a countertop, a refrigerator, and a window.
A park with picnic tables, a playground, and a large coniferous tree.
A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.
A kitchen with a refrigerator, a coffee maker, and a microwave.

15. The Villager Motel

The Villager Motel
Williamstown
United States
DONNA
CA $106
CA $119 total
includes taxes & fees
Nov 16 - Nov 17
The Villager Motel
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.
A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.
A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

16. Williamstown Motel

Williamstown Motel
Williamstown
United States
Ahmet
CA $101
CA $113 total
includes taxes & fees
Nov 5 - Nov 6
Williamstown Motel
An outdoor seating area with Adirondack chairs and potted plants.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

17. Cozy Corner Motel

Cozy Corner Motel
Williamstown
United States
Jonathan
CA $106
CA $125 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Corner Motel
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A hotel room with two beds, a chair, and a bedside table with a phone.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

18. Sunset Inn

Sunset Inn
Lee
United States
Lauren
CA $115
CA $128 total
includes taxes & fees
Nov 2 - Nov 3
Sunset Inn
A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.
A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.
A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.
A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

19. Blue Vista Motor Lodge

Blue Vista Motor Lodge
North Adams
United States
William
CA $261
CA $276 total
includes taxes & fees
Oct 26 - Oct 27
Blue Vista Motor Lodge
A hotel room with a bed, a desk, and two wall-mounted lamps.
A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.
A motel with a parking lot, a signboard, and a lawn with plants.
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

20. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
CA $93
CA $104 total
includes taxes & fees
Nov 6 - Nov 7
Econo Lodge Lee - Great Barrington
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Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Windsor.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
CA $114
CA $143 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (2,750 reviews)
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
CA $121
CA $167 total
Nov 10 - Nov 11
includes taxes & fees
Berkshire Mountain Lodge
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA
CA $169
CA $189 total
Nov 8 - Nov 9
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Windsor Hotel Reviews

The Whitlock

The Whitlock

10/10 Excellent
"This property was the perfect location to enjoy downtown Lennox and very close to our friends’ son’s wedding at Tanglewood. I’d stay again!"
Michelle 1-night trip
Posted 2 hours ago
The Whitlock

Find out more about Windsor

Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Windsor, Windsor you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions.

Several of the best hotels with 2 Stars in Windsor are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in Windsor.

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