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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 81 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, (2361)
"Safe "
The price is AED 391
AED 454 total
includes taxes & fees
9 Mar - 10 Mar
D. Hotel Suites & Spa
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (513)
"The restaurant and lounge area is so inviting, and staff is all around excellent."
The price is AED 355
AED 397 total
includes taxes & fees
19 Mar - 20 Mar
Life House Berkshires
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (426)
"Tradition ski inn with great common areas. "
The price is AED 450
AED 546 total
includes taxes & fees
9 Mar - 10 Mar
Mountaineer Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1007)
"This was a very nice little getaway from everyday life. The room was nice and roomy and we loved the fireplace. "
The price is AED 293
AED 328 total
includes taxes & fees
17 Mar - 18 Mar
The Yankee, Trademark Collection by Wyndham
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (419)
"Very nice boutique hotel in a wonderful college town. Winter season caused Wi-Fi, electricity and staff shortages. Overall nice stay. "
The price is AED 746
AED 833 total
includes taxes & fees
9 Mar - 10 Mar
The Williams Inn
Comfort Inn & Suites
Lobby

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Great service and very clean."
The price is AED 451
AED 504 total
includes taxes & fees
1 Apr - 2 Apr
Comfort Inn & Suites
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (186)
"Outdoor pool was great !"
The price is AED 933
AED 1,117 total
includes taxes & fees
1 Apr - 2 Apr
Mount Snow Grand Summit Resort
Hotel Downstreet, Ascend Hotel Collection
Indoor spa tub

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1004)
"Exactly what I needed after being stressed out from work for the past few months. The laundry service may have out of service, but I dont care. All I needed was to decompress and this hotel helped me do exactly that. Thank you for a lovely weekend and I'll definitely come back when I get the chance.😊"
The price is AED 434
AED 485 total
includes taxes & fees
20 Mar - 21 Mar
Hotel Downstreet, Ascend Hotel Collection
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, (1004)
"Some aspects were great, some not. The hotel restruant is an Indian cuisine which we do not like. The room we stayed in has wall and floor structural problems. There was also a camera pin hole in the ceiling over the tub I stuffed a tissue into. It was noisy between 10 to 11 pm as a group of loud drunks were walking down the hall."
The price is AED 359
AED 401 total
includes taxes & fees
13 Mar - 14 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
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, (606)
"It is convenient for families with little ones during the off-season to have fun with the pool-activities-arcade and movie theatre on site. It is an easy drive from areas of MA-NY and CT to make it a convenient family weekend get away-rooms are getting dated and could use some sprucing and updating but are overall clean "
The price is AED 437
AED 539 total
includes taxes & fees
9 Mar - 10 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Howard Johnson by Wyndham Amherst Hadley
Property amenity

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1005)
"Howard Johnson's is a reliable place to stay when I visit Amherst. It's clean, comfortable, affordable and conveniently located. Nothing posh or fancy about it, but it serves its purpose well. Mini fridge in room is a nice plus. Would be nice if they had in-room microwaves."
The price is AED 365
AED 408 total
includes taxes & fees
12 Mar - 13 Mar
Howard Johnson by Wyndham Amherst Hadley
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (439)
"Great room. Comfortable. Wished we stayed longer! Will definitely recommend to friends and family. "
The price is AED 437
AED 562 total
includes taxes & fees
16 Mar - 17 Mar
Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (745)
"Great location for my needs. Quiet and clean price was right as well. "
The price is AED 382
AED 427 total
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (964)
"Very nice and clean "
The price is AED 475
AED 530 total
includes taxes & fees
13 Mar - 14 Mar
Homewood Suites by Hilton Holyoke-Springfield/North
Red Roof Inn PLUS+ West Springfield
Lobby

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1005)
"Good"
The price is AED 311
AED 356 total
includes taxes & fees
12 Mar - 13 Mar
Red Roof Inn PLUS+ West Springfield
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet. "
The price is AED 511
AED 734 total
includes taxes & fees
31 Mar - 1 Apr
The Red Lion 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, (1010)
"Great place to stay has plenty of places around to shop and eat would stay again. Thank you for the experience "
The price is AED 356
AED 404 total
includes taxes & fees
23 Mar - 24 Mar
Tru by Hilton Chicopee Springfield
Best Western Bennington
In-room safe, blackout drapes, iron/ironing board

Best Western Bennington

2.5 star property
7.8 out of 10, Good, (822)
"I can always count on Steve at the front desk for a great experience at the Bennington BW."
The price is AED 389
AED 423 total
includes taxes & fees
13 Mar - 14 Mar
Best Western Bennington
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (657)
"Our stay was great at the Candlewood Suites. All of the staff were wonderful and very accommodating. The kids loved the pool and the snack room. Also, the one bedroom room was great for families and the bed was very comfortable. The location was great to go to the basketball hall of fame and MGM. It was also only 50 minutes to skiing. "
The price is AED 323
AED 370 total
includes taxes & fees
14 Mar - 15 Mar
Candlewood Suites West Springfield by IHG
The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (621)
"The place is attractive and comfortable. It's in a location convenient for restaurants and Smith College and they offer a good selection for breakfast."
The price is AED 474
AED 529 total
includes taxes & fees
10 Mar - 11 Mar
The Ellery
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, (1784)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is AED 400
AED 476 total
includes taxes & fees
10 Mar - 11 Mar
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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?
Listed below are some of the more popular apartments in the area to choose from: 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 12.9 mi/20.7 km from the heart of Windsor. Includes sofa beds. A fitness center and an indoor pool are on site. 1500 sqft private entrance with beautiful views of the Berkshire Mountains: It’s situated in Lee, 18 mi/29 km away. Includes free WiFi, private patios, and Smart TVs. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: 17.4 mi/28 km away in Lee. Private patios and fireplaces are included. Serene 2-bedroom apartment in North Adams.Plenty of off street parking.: It’s situated in North Adams, 13.4 mi/21.6 km from Windsor.
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.