Search B&B in Windsor

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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

D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2327)
"The elevator may be the slowest one in western MA, Also, the king size bed was not as comfortable as I remember from previous stays. The staff there are all terrific!"
The price is SAR 419
SAR 487 total
includes taxes & fees
7 Apr - 8 Apr
D. Hotel Suites & Spa
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (541)
"Quiet, quick, and easy stay. Clean simple rooms "
The price is SAR 405
SAR 453 total
includes taxes & fees
7 Apr - 8 Apr
Berkshires Untold
Howard Johnson by Wyndham Amherst Hadley
Property amenity

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1001)
"Was kind of nervous since the outside of the hotel looked sketchy and old however it was surprisingly decent. The free breakfast was delicious, the staff was nice and helpful, the room was clean. Will definitely stay here again next time I’m in the area. "
The price is SAR 373
SAR 417 total
includes taxes & fees
8 Apr - 9 Apr
Howard Johnson by Wyndham Amherst Hadley
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1003)
"big rooms, clean"
The price is SAR 471
SAR 527 total
includes taxes & fees
8 Apr - 9 Apr
Comfort Inn & Suites
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1006)
"Comfortable beds "
The price is SAR 332
SAR 371 total
includes taxes & fees
13 Apr - 14 Apr
The Yankee, Trademark Collection by Wyndham
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (676)
"Great rooms clean and great hot tub and pool"
The price is SAR 349
SAR 399 total
includes taxes & fees
12 Apr - 13 Apr
Candlewood Suites West Springfield by IHG
Quality Inn West Springfield
Lobby

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1001)
"The rooms are clean, the staff are efficient and friendly and the hotel was easy to find with lots of parking."
The price is SAR 303
SAR 347 total
includes taxes & fees
20 Apr - 21 Apr
Quality Inn West Springfield
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (615)
"Clean and great location "
The price is SAR 447
SAR 551 total
includes taxes & fees
7 Apr - 8 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Red Roof Inn PLUS+ West Springfield
Lobby

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1007)
"Only utilzed the Inn for rest/sleep; Inn was clean /comfortable at a reasonable price. Only issue/concern was outside noise by residents in the morning prior to departure."
The price is SAR 334
SAR 383 total
includes taxes & fees
14 Apr - 15 Apr
Red Roof Inn PLUS+ West Springfield
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Excellent"
The price is SAR 348
SAR 388 total
includes taxes & fees
13 Apr - 14 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (435)
"조용하고 깨끗한 룸이 마음에 들었지만 힛팅 소리가 크게들려 중간에 잠이 깼다 "
The price is SAR 909
SAR 1,016 total
includes taxes & fees
7 Apr - 8 Apr
The Williams Inn
The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (646)
"Very clean and cozy."
The price is SAR 522
SAR 583 total
includes taxes & fees
8 Apr - 9 Apr
The Ellery
Homewood Suites by Hilton Holyoke-Springfield/North
Exterior

Homewood Suites by Hilton Holyoke-Springfield/North

3.0 star property
9.0 out of 10, Wonderful, (984)
"Nice property--room was comfortable and clean, breakfast was excellent, and staff were friendly."
The price is SAR 475
SAR 531 total
includes taxes & fees
21 Apr - 22 Apr
Homewood Suites by Hilton Holyoke-Springfield/North
Tru by Hilton Chicopee Springfield
Premium bedding, down comforters, blackout drapes, iron/ironing board

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1002)
"First time stating a tru hotel. The bed and pillows were comfortably. I LOVED early check in 3pm and late checkout at 12pm. That extra hour makes a huge difference. They dont have an actual closet just an small area to hang up clothes , room could ealy looks messy clothes in the open. That will not deter me from staying again late check OUT YES. "
The price is SAR 422
SAR 479 total
includes taxes & fees
21 Apr - 22 Apr
Tru by Hilton Chicopee Springfield
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"The staff was absolutely amazing, very accommodating and friendly. Overall we had a wonderful experience!! "
The price is SAR 397
SAR 612 total
includes taxes & fees
30 Apr - 1 May
The Red Lion Inn
Hotel Downstreet, Ascend Hotel Collection
Exterior

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1002)
"We have been here about 5 times. Greay location. Good price."
The price is SAR 475
SAR 531 total
includes taxes & fees
27 Apr - 28 Apr
Hotel Downstreet, Ascend Hotel Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (437)
"This inn is located in a very convenient location to the town center where there are numerous boutique shops. The inn itself is quiet, clean, and safe, with a small 24-hour open dining room with a coffee station that offers Green Mountain coffee pods, and pop-corn and cracker snacks. The stay includes a breakfast that consists of cold items -- cereals, yogurt, croissants, hard-boiled eggs, etc. But the town center is but a stone's throw away with a few excellent locations for a full breakfast. "
The price is SAR 305
SAR 340 total
includes taxes & fees
4 May - 5 May
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Comfort Inn & Suites
Indoor pool

Comfort Inn & Suites

2.5 star property
7.6 out of 10, Good, (808)
"We had a great room with a fireplace very relaxing and a great surprise for our valentines get away. Thanks "
The price is SAR 380
SAR 434 total
includes taxes & fees
9 Apr - 10 Apr
Comfort Inn & Suites
Quality Inn & Suites Northampton - Amherst
Deluxe Room, 2 Queen Beds, Non Smoking | Desk, iron/ironing board, cribs/infant beds, rollaway beds

Quality Inn & Suites Northampton - Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"Very plain appearance on outside. Beds very comfortable. Room darkened well. Room heat easily adjustable. Other than beds, nothing great; nothing terrible."
The price is SAR 412
SAR 460 total
includes taxes & fees
9 Apr - 10 Apr
Quality Inn & Suites Northampton - Amherst
Inn on Boltwood
Balcony

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (637)
"Overall, a great place to stay. The staff were fantastic -- and the outdoor gathering/firepit space is just lovely, weather permitting."
The price is SAR 897
SAR 1,002 total
includes taxes & fees
8 Apr - 9 Apr
Inn on Boltwood
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windsor

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1794)
"The location to jimney peak was great."
The price is SAR 389
SAR 467 total
includes taxes & fees
16 Apr - 17 Apr
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, (926)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 552 total
includes taxes & fees
7 Apr - 8 Apr
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 855 total
includes taxes & fees
7 Apr - 8 Apr
Berkshire Village Carriage House - Super Private!!
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 & The Berkshires: 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. Situated 17.4 mi (28 km) from the heart of Windsor. 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.