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Search Resort Hotels in Windsor from CA $100

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
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, (926 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
The price is CA $90
CA $100 total
includes taxes & fees
Oct 27 - Oct 28
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, (281 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
Nov 22 - Nov 23
Rodeway Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

3. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Breakfast was great"
United States
Thomas
The price is CA $154
CA $172 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

4. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (938 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is CA $120
CA $135 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire 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, (1,003 reviews)
"The location was good for our trip."
United States
Basil
The price is CA $134
CA $150 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A building entrance with a large planter with purple flowers and a small tree.

6. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (960 reviews)
"This was an excellent hotel. Super convenient right in the middle of town, clean, huge rooms, historic, and comfortable, I would love to stay here again I would recommend it to anyone!"
United States
Devon
The price is CA $162
CA $180 total
includes taxes & fees
Nov 8 - Nov 9
Hotel On North
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (428 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $139
CA $155 total
includes taxes & fees
Oct 27 - Oct 28
The Central Downtown Inn & Suites
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.

8. 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
The price is CA $212
CA $236 total
includes taxes & fees
Nov 2 - Nov 3
The Trail in Adams - Berkshires’ Art Hotel
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

9. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,225 reviews)
"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."
United States
ulla
The price is CA $119
CA $165 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (929 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
The price is CA $111
CA $124 total
includes taxes & fees
Oct 26 - Oct 27
Howard Johnson by Wyndham Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.

11. 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, (244 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
The price is CA $133
CA $149 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A living room with a fireplace, two sofas, and four black side tables.

12. 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
The price is CA $193
CA $216 total
includes taxes & fees
Nov 2 - Nov 3
The Revival House
A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

13. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,002 reviews)
"Great experience and Great onsite restaurant."
United States
mary ellen
The price is CA $167
CA $186 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Downstreet, an Ascend Collection Hotel
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

14. 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
The price is CA $137
CA $153 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Berkshire Hills Inn & Suites
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

15. 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 $294 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire Village Carriage House - Super Private!!
A patio area with outdoor furniture, a fire pit, and potted plants.

16. 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
The price is CA $148
CA $162 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

17. 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
The price is CA $166
CA $186 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
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, (2,784 reviews)
"We had an amazing stay."
United States
Luke
The price is CA $113
CA $141 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
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.

19. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (363 reviews)
"Excellent service, excellent stay."
United States
Ahmet
The price is CA $101
CA $113 total
includes taxes & fees
Nov 1 - Nov 2
Williamstown Motel
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

20. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is CA $287
CA $669 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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
"Good price, affordable, a lot of amenities. A little dated but nothing was in need of repair just an update. There’s free laundry, a pool, movie night, activity list for the week you’re there. It’s a good place to stay! I will say we did lose power for 9 hours and they kept us up to date but nothing was offered for the inconvenience which was a bit disappointing as we had food in the fridge. Overall, recommend!"
Madisson 7-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Find out more about Windsor

Windsor Resorts information

Number of reviews
13,513
Accommodation
8 Resorts
Lowest Price
CA $100
Highest Price
CA $669

Frequently asked questions

What is Windsor like for a resort vacation?
You deserve a getaway, and a resort is the perfect place to pamper yourself with the amenities and services you need for a relaxing stay in Windsor. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, blissful spa treatments, or nightly entertainment options.
What's a favorite resort for my stay in Windsor?
Our top-rated resorts near Windsor: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Windsor. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 12.8 mi (20.7 km) from Windsor. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
What can I do in Windsor?
Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Pontoosuc Lake are a few interesting places to visit nearby. In the area, other attractions include Swift River and Mount Greylock.
What's the weather like in Windsor?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Windsor?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the city center. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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