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Windsor Condominium Resorts to Rent

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

1. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (927 reviews)
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
United States
Richard
$65 nightly
The price is $72
Nov 12 - Nov 13
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.

2. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (282 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
Nov 26 - Nov 27
Total with taxes and fees
Rodeway Inn
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

3. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (967 reviews)
"Big spacious rooms, great bed, great bath."
United States
John
$128 nightly
The price is $143
Nov 8 - Nov 9
Total with taxes and fees
Hotel On North
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, (1,010 reviews)
"The location was good for our trip."
United States
Basil
$105 nightly
The price is $117
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (930 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 29 - Oct 30
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (431 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Oct 29 - Oct 30
Total with taxes and fees
The Central Downtown Inn & Suites
Exterior

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,237 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
$118 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

8. 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, (248 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
$101 nightly
The price is $113
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
$151 nightly
The price is $169
Nov 4 - Nov 5
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A living room with a fireplace, two sofas, and four black side tables.

10. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (42 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
$150 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
The Revival House
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, (122 reviews)
"Loved the vibe!"
United States
Elizabeth
$106 nightly
The price is $116
Nov 1 - Nov 2
Total with taxes and fees
The Springs Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

12. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (940 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$79 nightly
The price is $88
Nov 26 - Nov 27
Total with taxes and fees
Berkshire Inn
A hotel patio with outdoor seating and a fire pit.

13. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 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 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, (1,004 reviews)
"Great experience and Great onsite restaurant."
United States
mary ellen
$119 nightly
The price is $133
Nov 17 - Nov 18
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, (1,003 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

16. 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.
$189 nightly
The price is $211
Oct 29 - Oct 30
Total with taxes and fees
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.

17. 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, (1,000 reviews)
"Room was spacious and clean"
United States
James
$93 nightly
The price is $104
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

18. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,802 reviews)
"We had an amazing stay."
United States
Luke
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

19. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (365 reviews)
"Excellent service, excellent stay."
United States
Ahmet
$73 nightly
The price is $82
Nov 1 - Nov 2
Total with taxes and fees
Williamstown Motel
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

20. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,054 reviews)
"A very good place to stay"
United States
Madhavi R
$133 nightly
The price is $149
Nov 3 - Nov 4
Total with taxes and fees
Berkshires Untold
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

The Yankee Inn

The Yankee Inn

8/10 Good
"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"
Jeanne 1-night trip
Posted 2 hours ago
The Yankee Inn

Find out more about Windsor

Windsor Condo Resorts information

Number of reviews
8,611
Accommodation
0 Condo Resorts
Lowest Price
$72
Highest Price
$211

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