Default HTG hotel image

Best Resorts in Windsor

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13
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, (924 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 4 - Nov 5
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, (279 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 3 - Nov 4
Total with taxes and fees
Rodeway Inn
A living room with a fireplace, two sofas, and four black side tables.

3. 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
$138 nightly
The price is $154
Nov 5 - Nov 6
Total with taxes and fees
The Revival House
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 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 entrance with a large planter with purple flowers and a small tree.

5. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (956 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
$142 nightly
The price is $158
Nov 1 - Nov 2
Total with taxes and fees
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

6. 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, (239 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
$95 nightly
The price is $106
Nov 17 - Nov 18
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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, (425 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$89 nightly
The price is $100
Oct 22 - Oct 23
Total with taxes and fees
The Central Downtown Inn & Suites
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

8. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (937 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$79 nightly
The price is $88
Nov 17 - Nov 18
Total with taxes and fees
Berkshire Inn
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, (1,213 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$110 nightly
The price is $123
Nov 18 - Nov 19
Total with taxes and fees
Berkshire Mountain Lodge
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

10. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (300 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
$189 nightly
The price is $211
Oct 19 - Oct 20
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
Room

11. 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, (1,000 reviews)
"enjoyed our stay"
United States
Mark
$105 nightly
The price is $117
Nov 7 - Nov 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

12. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (927 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 19 - Oct 20
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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.
$439 nightly
The price is $490
Oct 19 - Oct 20
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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.

14. 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
$160 nightly
The price is $179
Nov 18 - Nov 19
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.

15. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
$110 nightly
The price is $122
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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, (121 reviews)
"Loved the vibe!"
United States
Elizabeth
$105 nightly
The price is $115
Nov 18 - Nov 19
Total with taxes and fees
The Springs Motel
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

17. 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
$233 nightly
The price is $247
Nov 17 - Nov 18
Total with taxes and fees
Harbour House Inn
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

18. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,003 reviews)
"Great experience and Great onsite restaurant."
United States
mary ellen
$119 nightly
The price is $133
Nov 8 - Nov 9
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A hotel patio with outdoor seating and a fire pit.

19. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (714 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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.

20. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (363 reviews)
"Excellent service, excellent stay."
United States
Ahmet
$73 nightly
The price is $82
Nov 2 - Nov 3
Total with taxes and fees
Williamstown Motel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Windsor

Windsor Resorts information

Number of reviews
8,160
Accommodation
8 Resorts
Lowest Price
$72
Highest Price
$490

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.

Explore a world of travel with Expedia