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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 96 Apartments 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, (2325)
"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 AED 443
AED 514 total
includes taxes & fees
6 Apr - 7 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 AED 397
AED 443 total
includes taxes & fees
6 Apr - 7 Apr
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1006)
"Great location and the room was very nice. The only issue I had was the bed was very firm. "
The price is AED 325
AED 363 total
includes taxes & fees
13 Apr - 14 Apr
The Yankee, Trademark Collection by Wyndham
Howard Johnson by Wyndham Amherst Hadley
Property amenity

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1000)
"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 AED 362
AED 405 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 AED 461
AED 515 total
includes taxes & fees
8 Apr - 9 Apr
Comfort Inn & Suites
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 AED 803
AED 897 total
includes taxes & fees
6 Apr - 7 Apr
The Williams Inn
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (675)
"Great rooms clean and great hot tub and pool"
The price is AED 342
AED 391 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 AED 297
AED 339 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 AED 437
AED 540 total
includes taxes & fees
6 Apr - 7 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1000)
"Excellent"
The price is AED 340
AED 380 total
includes taxes & fees
13 Apr - 14 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection
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 AED 327
AED 375 total
includes taxes & fees
13 Apr - 14 Apr
Red Roof Inn PLUS+ West Springfield
The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (646)
"Very clean and cozy."
The price is AED 511
AED 570 total
includes taxes & fees
6 Apr - 7 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 AED 465
AED 520 total
includes taxes & fees
21 Apr - 22 Apr
Homewood Suites by Hilton Holyoke-Springfield/North
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (451)
"Easy check on thru text. No staff after 4PM. Cozy place and room was nice. Close to Mount Snow ski area."
The price is AED 372
AED 451 total
includes taxes & fees
8 Apr - 9 Apr
Mountaineer Inn
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 AED 399
AED 452 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 AED 393
AED 604 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 AED 465
AED 520 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 AED 298
AED 333 total
includes taxes & fees
4 May - 5 May
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Hampton Inn West Springfield
Seasonal outdoor pool

Hampton Inn West Springfield

2.5 star property
8.4 out of 10, Very Good, (1000)
"Well taken care of."
The price is AED 434
AED 497 total
includes taxes & fees
13 Apr - 14 Apr
Hampton Inn West Springfield
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 AED 403
AED 450 total
includes taxes & fees
8 Apr - 9 Apr
Quality Inn & Suites Northampton - 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
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 AED 380
AED 458 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 AED 493
AED 540 total
includes taxes & fees
6 Apr - 7 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 AED 551
AED 837 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

What's it like to stay at an apartment in Windsor?
You might not have many choices centrally in Windsor, but Expedia can help you find lodging options in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages.
Are you thinking about an apartment for your stay?
An apartment features a kitchen for convenient meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families who want the conveniences of home.
What's a favorite apartment for a stay in Windsor?
Here are some of the top apartments in the area to choose from: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Situated in Lee, 17.4 mi/28 km from the heart of Windsor. Includes private patios and fireplaces. 51 Church Street, Lenox MA - One Bedroom Unit: Located 16 mi/25.7 km away in Lenox. The Studio mini home away from home in the Berkshires: 17.3 mi/27.9 km away in Lee. Amenities include private patios. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 12.9 mi/20.7 km from Windsor. Includes sofa beds. A fitness center and an indoor pool are on site.
What can I expect from the weather during my trip to Windsor?
Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay 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 should I see and do in Windsor?
While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Wahconah Falls State Park. In the larger area, you’ll find Mount Greylock State Reservation Visitor Center and Swift River.
What's the best way to get to and around Windsor?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away from the city center. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.