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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
$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, (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
$64 nightly
The price is $71
Nov 1 - Nov 2
Total with taxes and fees
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
$110 nightly
The price is $122
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A building entrance with a large planter with purple flowers and a small tree.

4. 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
$132 nightly
The price is $148
Nov 10 - Nov 11
Total with taxes and fees
Hotel On North
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.

5. 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
$144 nightly
The price is $161
Nov 2 - Nov 3
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

6. 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
$79 nightly
The price is $88
Nov 23 - Nov 24
Total with taxes and fees
Berkshire Inn
Two Adirondack chairs facing a river with a forested hill in the background.

7. 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
$101 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (427 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Oct 25 - Oct 26
Total with taxes and fees
The Central Downtown Inn & Suites
A living room with a fireplace, two sofas, and four black side tables.

9. 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 spacious lobby with a fireplace, multiple seating areas, and a chandelier.

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,224 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$110 nightly
The price is $123
Nov 23 - Nov 24
Total with taxes and fees
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.

11. 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
$79 nightly
The price is $88
Oct 25 - Oct 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.

12. 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
$95 nightly
The price is $106
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

13. 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 26 - Oct 27
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

14. 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.
$424 nightly
The price is $474
Nov 9 - Nov 10
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

15. 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 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
$106 nightly
The price is $116
Nov 1 - Nov 2
Total with taxes and fees
The Springs Motel
A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

17. 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
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
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.

18. 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
$98 nightly
The price is $109
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
$254 nightly
The price is $268
Oct 28 - Oct 29
Total with taxes and fees
Harbour House Inn
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

20. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,782 reviews)
"We had an amazing stay."
United States
Luke
$117 nightly
The price is $131
Nov 23 - Nov 24
Total with taxes and fees
Vacation Village in the Berkshires
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

Hotel On North

Hotel On North

10/10 Excellent
"Charming hotel, far exceeded expectations. Clean. Well managed. Stayed for a girls weekend and enjoyed the area and surrounding towns. Would highly recommend."
Amie 2-night trip
Posted 4 hours ago
Hotel On North

Find out more about Windsor

Windsor Inns information

Number of reviews
13,567
Accommodation
3 Inns
Lowest Price
$71
Highest Price
$474

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