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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (978 reviews)
"Very nice hotel"
United States
Philip
$119 nightly
The price is $133
Nov 29 - Nov 30
Total with taxes and fees
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
$79 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
FairBridge Inn Express
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

3. 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
$67 nightly
The price is $75
Dec 6 - Dec 7
Total with taxes and fees
Rodeway Inn
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"The location was good for our trip."
United States
Basil
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
The Yankee Inn
A living room with a fireplace, two sofas, and four black side tables.

5. 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
$138 nightly
The price is $154
Nov 16 - Nov 17
Total with taxes and fees
The Revival House
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
$99 nightly
The price is $111
Dec 4 - Dec 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

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
$79 nightly
The price is $88
Dec 6 - Dec 7
Total with taxes and fees
Berkshire Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (934 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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.

9. 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
$156 nightly
The price is $175
Nov 15 - Nov 16
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Exterior

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,256 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
$102 nightly
The price is $113
Dec 6 - Dec 7
Total with taxes and fees
Berkshire Mountain Lodge
A patio area with outdoor furniture, a fire pit, and potted plants.

11. 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
$89 nightly
The price is $97
Nov 9 - Nov 10
Total with taxes and fees
The Springs Motel
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

12. 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
$99 nightly
The price is $111
Nov 8 - Nov 9
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

13. 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
$93 nightly
The price is $104
Dec 1 - Dec 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

14. 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
$119 nightly
The price is $133
Nov 19 - Nov 20
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A spacious hotel lobby with multiple seating areas, large windows, and a television.

15. 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
$110 nightly
The price is $122
Nov 11 - Nov 12
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

16. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (366 reviews)
"Excellent service, excellent stay."
United States
Ahmet
$76 nightly
The price is $85
Nov 19 - Nov 20
Total with taxes and fees
Williamstown Motel
A hotel patio with outdoor seating and a fire pit.

17. 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
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

18. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (685 reviews)
"Great stay!"
United States
Vandhana
$126 nightly
The price is $140
Nov 15 - Nov 16
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

19. 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
$226 nightly
The price is $239
Dec 1 - Dec 2
Total with taxes and fees
Harbour House Inn
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

20. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (528 reviews)
"Great stay"
United States
Ram
$181 nightly
The price is $202
Dec 6 - Dec 7
Total with taxes and fees
The Porches Inn at Mass MoCA
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 Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"It's a good place with beautiful views during the 🍁🍂 for a family or romantic get away"
fritzgerald 2-night trip
Posted 8 hours ago
Vacation Village in the Berkshires

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
787
Accommodation
27 Condo Rentals
Lowest Price
$75
Highest Price
$239

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