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Best Resorts in Windsor

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
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, (983 reviews)
"Very nice hotel"
United States
Philip
$112 nightly
The price is $125
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, (936 reviews)
"Friendly staff"
United States
William
$79 nightly
The price is $88
Nov 11 - Nov 12
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, (285 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
$65 nightly
The price is $72
Dec 10 - Dec 11
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, (1,007 reviews)
"What a beautiful stay. Room was so clean ! Great food selection for breakfast."
United States
Stephanie
$114 nightly
The price is $127
Nov 12 - Nov 13
Total with taxes and fees
The Yankee Inn
Exterior

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
"Excellent stay!!!!"
United States
Susan J
$108 nightly
The price is $120
Dec 10 - Dec 11
Total with taxes and fees
Berkshire Mountain Lodge
A living room with a fireplace, two sofas, and four black side tables.

6. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
"Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7"
United States
Ruby
$150 nightly
The price is $168
Nov 15 - Nov 16
Total with taxes and fees
The Revival House
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, (942 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$85 nightly
The price is $95
Dec 11 - Dec 12
Total with taxes and fees
Berkshire Inn
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
9.4 out of 10, Exceptional, (258 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
$110 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A patio area with outdoor furniture, a fire pit, and potted plants.

9. 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
$106 nightly
The price is $116
Dec 10 - Dec 11
Total with taxes and fees
The Springs Motel
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, (937 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Nov 11 - Nov 12
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

11. 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
$223 nightly
The price is $236
Dec 1 - Dec 2
Total with taxes and fees
Harbour House Inn
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, (436 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$93 nightly
The price is $104
Nov 13 - Nov 14
Total with taxes and fees
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.

13. 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
$173 nightly
The price is $193
Dec 11 - Dec 12
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
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, (1,003 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 17 - Nov 18
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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, (717 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 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, (302 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
$180 nightly
The price is $201
Nov 15 - Nov 16
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
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.

17. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (369 reviews)
"Yes no frills but good for an economic stay. Great coffee at The Coffee Shop Williamstown nearby"
United States
Grantley
$81 nightly
The price is $90
Nov 11 - Nov 12
Total with taxes and fees
Williamstown Motel
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
$270 nightly
The price is $301
Nov 11 - Nov 12
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Room

19. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,006 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
$119 nightly
The price is $133
Nov 24 - Nov 25
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.

20. 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, (1,002 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
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

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good
"Registration assistant was very pleasant. The room was clean and the bed was quite comfortable."
barbara 1-night trip
Posted 1 hour ago
Red Roof Inn PLUS+ South Deerfield – Amherst
Hotel On North

Hotel On North

10/10 Excellent
"Staff very pleasant and accommodating."
Rosemarie 4-night trip
Posted 3 hours ago
Hotel On North

Find out more about Windsor

Windsor Resorts information

Number of reviews
3,948
Accommodation
8 Resorts
Lowest Price
$72
Highest Price
$301

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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