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Compare 26 B&B in Windsor with updated reviews, rates, and availability.

D. Hotel Suites & Spa
Front of property

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2343)
"Staff was great! "
The price is AED 447
AED 517 total
includes taxes & fees
28 Dec - 29 Dec
D. Hotel Suites & Spa
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (458)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."
The price is AED 326
AED 364 total
includes taxes & fees
9 Jan - 10 January 2025
Life House Berkshires
Quality Inn West Springfield
Exterior

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1002)
"Good service "
The price is AED 316
AED 361 total
includes taxes & fees
20 Jan - 21 January 2025
Quality Inn West Springfield
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great check in experience. "
The price is AED 356
AED 398 total
includes taxes & fees
7 Jan - 8 January 2025
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Love the view of the lake while having breakfast!"
The price is AED 372
AED 415 total
includes taxes & fees
2 Jan - 3 January 2025
The Black Swan Lee - Lenox, Ascend Hotel Collection
Homewood Suites by Hilton Holyoke-Springfield/North
Terrace/patio

Homewood Suites by Hilton Holyoke-Springfield/North

3.0 star property
9.0 out of 10, Wonderful, (928)
"Nice rooms"
The price is AED 465
AED 520 total
includes taxes & fees
7 Jan - 8 January 2025
Homewood Suites by Hilton Holyoke-Springfield/North
Howard Johnson by Wyndham Amherst Hadley
Room

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1001)
"For me it is the place to stay, because of proximity to the college and university, the mall, the dining options, downtown Amherst and the friendliness of the staff, the smooth registration, and the value-for-money."
The price is AED 372
AED 415 total
includes taxes & fees
1 Jan - 2 January 2025
Howard Johnson by Wyndham Amherst Hadley
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Lively plae"
The price is AED 320
AED 522 total
includes taxes & fees
9 Jan - 10 January 2025
The Red Lion Inn
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (355)
"Perfectly fine little place to stay while in Vermont. Unbelievably convenient location right off the base of Mount Snow, but at a fraction of the price of the lodges at the resort. Easy check in and comfortable beds. Complementary coffee and snacks as well. 2nd time staying here and will definitely consider them again next time."
The price is AED 528
AED 640 total
includes taxes & fees
8 Jan - 9 January 2025
Mountaineer Inn
Comfort Inn & Suites
Exterior

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1001)
"It was all good "
The price is AED 465
AED 520 total
includes taxes & fees
1 Jan - 2 January 2025
Comfort Inn & Suites
Tru by Hilton Chicopee Springfield
Exterior

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1006)
"Great experience and descent breakfast with all the items such, cereal, eggs, protein, yogurt, pancakes, milk, juice, coffee and more."
The price is AED 340
AED 386 total
includes taxes & fees
2 Jan - 3 January 2025
Tru by Hilton Chicopee Springfield
The Ellery
Exterior

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (563)
"Just a lovely place. "
The price is AED 511
AED 570 total
includes taxes & fees
29 Dec - 30 Dec
The Ellery
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (574)
"It was nice an omar the worker in the game room is very nice.helpful and grate personality....an the place was clean an nice"
The price is AED 474
AED 581 total
includes taxes & fees
6 Jan - 7 January 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Red Roof Inn PLUS+ West Springfield
Exterior

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1004)
"Price"
The price is AED 321
AED 367 total
includes taxes & fees
29 Dec - 30 Dec
Red Roof Inn PLUS+ West Springfield
Hotel UMass
Lobby sitting area

Hotel UMass

2.5 star property
8.8 out of 10, Excellent, (925)
"Ver clean, big room. Pillows were not comfortable. Nice breakfast. Cute lobby"
The price is AED 528
AED 597 total
includes taxes & fees
5 Jan - 6 January 2025
Hotel UMass
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (170)
"👍"
The price is AED 1,029
AED 1,231 total
includes taxes & fees
22 Jan - 23 January 2025
Mount Snow Grand Summit Resort
Courtyard by Marriott Hadley Amherst
Reception

Courtyard by Marriott Hadley Amherst

3.0 star property
9.0 out of 10, Wonderful, (591)
"Great place!"
The price is AED 621
AED 693 total
includes taxes & fees
29 Dec - 30 Dec
Courtyard by Marriott Hadley Amherst
Comfort Inn & Suites
Exterior

Comfort Inn & Suites

2.5 star property
7.6 out of 10, Good, (780)
"It was a good stay BUT the shower was horrible. The water was only warm, and we are in the middle of winter, and the shower head was not strong. It was only a trickle of water coming out. I was very disappointed with the shower. The actual stay was good. The continental breakfast was good. The pool was nice and clean but the pool water was really cold too cold for it being winter her winter days. The room old looking but clean and it smelled really good. "
The price is AED 372
AED 425 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites
Hampton Inn West Springfield
Pool

Hampton Inn West Springfield

2.5 star property
8.4 out of 10, Very Good, (1001)
"A nice stay in a busy area. The rooms were nice.., not very large and could use a comfortable chair. However, staff were friendly and professional. Would stay again."
The price is AED 390
AED 447 total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn West Springfield
Homewood Suites by Hilton Hadley Amherst
Exterior

Homewood Suites by Hilton Hadley Amherst

3.0 star property
9.4 out of 10, Exceptional, (606)
"Great hotel with friendly people. Suite was beautiful and comfortable. "
The price is AED 559
AED 624 total
includes taxes & fees
2 Jan - 3 January 2025
Homewood Suites by Hilton Hadley Amherst
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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Other property types in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.

Frequently asked questions

Searching for B&Bs in Windsor?
If you want to find an accommodation with fewer rooms than the traditional hotel and a cozy environment, a B&B may be the perfect thing for your trip to Windsor.
How do you know if a B&B is the right choice for you?
B&Bs all have a unique charm. Whether it’s a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Windsor?
Below are some well-liked B&Bs in the area: The Cornell Inn, Lenox: 15.6 mi (25.1 km) from the heart of Windsor. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 16.8 mi (27 km) from the downtown core. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. 17.4 mi (28 km) from the heart of downtown. Enjoy the private yard and deli.
When is the best time to book my B&B in Windsor?
When you’re planning your escape to Windsor, year-round temperatures and rainfall may be important factors to consider. 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 is there to do in Windsor?
Spend some time exploring Savoy Mountain State Forest and Mohawk Trail State Forest if you’re hoping to see some of the area’s natural features. You might put Berkshire East Ski Resort and Jiminy Peak Mountain Resort on your list if you want to see more of the area.
How can I get to and around Windsor?
Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you’d like to explore around the area, you may want a rental car for your journey.