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Best Resorts in Windsor

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Windsor

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 reviews)
"Very nice and convenient hotel."
United States
Karen
$116 nightly
The price is $130
Sep 22 - Sep 23
Total with taxes and fees
The Yankee Inn
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

2. 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, (1,010 reviews)
"It was clean and amenities were above average."
United States
Prasanna
$90 nightly
The price is $100
Sep 9 - Sep 10
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

3. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (894 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
$62 nightly
The price is $69
Sep 15 - Sep 16
Total with taxes and fees
FairBridge Inn Express

4. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,001 reviews)
"Look good for being under constructikn"
United States
Debra
$118 nightly
The price is $132
Sep 10 - Sep 11
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,131 reviews)
"Clean & comfortable stay"
United States
Robert
$113 nightly
The price is $126
Oct 1 - Oct 2
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, (37 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
$166 nightly
The price is $185
Sep 7 - Sep 8
Total with taxes and fees
The Revival House
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

7. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (275 reviews)
"Room was very clean and spacious. Front desk personnel were extremely friendly and helpful. Downside was proximity and noise from road. Made for a noisy night"
United States
Brandie
$72 nightly
The price is $81
Oct 5 - Oct 6
Total with taxes and fees
Rodeway 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
9.2 out of 10, Wonderful, (194 reviews)
"Clean & easy to stay there"
United States
Steve
$127 nightly
The price is $142
Sep 10 - Sep 11
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A building entrance with a large planter with purple flowers and a small tree.

9. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (909 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
$152 nightly
The price is $170
Sep 7 - Sep 8
Total with taxes and fees
Hotel On North
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, (909 reviews)
"Stay again"
United States
irene
$78 nightly
The price is $87
Sep 17 - Sep 18
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

11. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (919 reviews)
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
United States
Ellen
$82 nightly
The price is $91
Oct 7 - Oct 8
Total with taxes and fees
Berkshire Inn
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.

12. 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, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
$169 nightly
The price is $189
Oct 1 - Oct 2
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.

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
$112 nightly
The price is $125
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A patio area with outdoor furniture, a fire pit, and potted plants.

14. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (117 reviews)
"Loved the vibe!"
United States
Elizabeth
$114 nightly
The price is $125
Sep 13 - Sep 14
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.

15. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very Good, (407 reviews)
"Large, clean, comfortable suite."
United States
Rena
$99 nightly
The price is $111
Sep 8 - Sep 9
Total with taxes and fees
The Central Downtown Inn & Suites
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

16. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
$224 nightly
The price is $236
Sep 17 - Sep 18
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.

17. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,611 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
$122 nightly
The price is $136
Sep 7 - Sep 8
Total with taxes and fees
Vacation Village in the Berkshires
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, (31 reviews)
"Excellent area for hiking the Berkshires! House is clean, comfortable, and perfect for cooking a quick dinner after showering off the mud and pine needles. Dog friendly. Right off the main street of a very nice neighborhood."
United States
Elizabeth G.
$290 nightly
The price is $323
Sep 10 - Sep 11
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

19. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Hotel was clean and stag was helpful and friendly."
United States
Basil
$143 nightly
The price is $160
Sep 27 - Sep 28
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A building with a covered parking area and a grassy front yard.

20. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (940 reviews)
"Great place"
United States
Donna
$100 nightly
The price is $112
Sep 7 - Sep 8
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Comfy, clean and central to many Berkshires gems"
Deborah 1-night trip
Posted 4 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Resorts information

Number of reviews
8,963
Accommodation
12 Resorts
Lowest Price
$69
Highest Price
$236

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: COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 12.9 mi (20.8 km) from Windsor. Has ski-in/ski-out access, a fitness center, and beach sun loungers. 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. Enjoy the ski-in/ski-out access, fitness center, and garden. Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 12.8 mi (20.7 km) from Windsor. Access to a fitness center, an indoor pool, and an outdoor 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 Mount Greylock and Barrington Stage Company.
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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