Search Residences in Windsor from CA $93

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Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
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Dec 4 - Dec 6
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Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

A building entrance with a large planter with purple flowers and a small tree.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (980 reviews)
"Very nice hotel"
United States
Philip
The price is CA $162
CA $181 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

2. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (934 reviews)
"Friendly staff"
United States
William
The price is CA $99
CA $111 total
includes taxes & fees
Nov 8 - Nov 9
FairBridge Inn Express
A living room with a fireplace, two sofas, and four black side tables.

3. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (44 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is CA $193
CA $216 total
includes taxes & fees
Nov 16 - Nov 17
The Revival House
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

4. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (284 reviews)
"The motel was clean and somewhat updated. Check in and check out was easy. Across the street was a yummy pizzeria."
United States
Joann
The price is CA $94
CA $105 total
includes taxes & fees
Dec 6 - Dec 7
Rodeway Inn
Two Adirondack chairs facing a river with a forested hill in the background.

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The location was good for our trip."
United States
Basil
The price is CA $152
CA $170 total
includes taxes & fees
Dec 6 - Dec 7
The Yankee Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is CA $144
CA $161 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

7. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is CA $113
CA $126 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Inn
Exterior

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $107
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
Room

9. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,000 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $167
CA $186 total
includes taxes & fees
Nov 23 - Nov 24
Hotel Downstreet, an Ascend Collection Hotel
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

10. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $238
CA $266 total
includes taxes & fees
Dec 7 - Dec 8
The Trail in Adams - Berkshires’ Art Hotel
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,000 reviews)
"enjoyed our stay"
United States
Mark
The price is CA $144
CA $161 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A patio area with outdoor furniture, a fire pit, and potted plants.

12. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (123 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is CA $131
CA $144 total
includes taxes & fees
Dec 1 - Dec 2
The Springs Motel
A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

13. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $294
CA $311 total
includes taxes & fees
Dec 1 - Dec 2
Harbour House Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"Breakfast was great"
United States
Thomas
The price is CA $153
CA $171 total
includes taxes & fees
Nov 14 - Nov 15
Hampton Inn & Suites Berkshires-Lenox
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

15. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $138
CA $155 total
includes taxes & fees
Nov 8 - Nov 9
The Central Downtown Inn & Suites
Indoor pool

16. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $112
CA $141 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

17. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (935 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
The price is CA $110
CA $123 total
includes taxes & fees
Nov 8 - Nov 9
Howard Johnson by Wyndham Lenox
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

18. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (301 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is CA $189
CA $279 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Village Carriage House - Super Private!!
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

19. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is CA $131
CA $146 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Berkshire Hills Inn & Suites
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

20. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is CA $166
CA $185 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Lenox Pittsfield
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.
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Top reviews in Windsor

A building entrance with a large planter with purple flowers and a small tree.
Hotel On North

Hotel On North

Hotel On North
Pittsfield

10/10 Excellent

This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
Canada
alan
Reviewed October 8, 2026
Hotel On North

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