Windsor, MA Apartments from AED 661

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Our top choices for Windsor apartments

2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls

AED 661 total

includes taxes & fees

6 Jul - 7 Jul

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

AED 685 total

includes taxes & fees

7 Jul - 8 Jul

2-Bdr Apt In Town, By the Water

Williamstown

Dan R.

AED 1,058 total

includes taxes & fees

8 Jul - 9 Jul

Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

AED 1,083 total

includes taxes & fees

8 Jul - 9 Jul

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Jen B.

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Hancock

Neil J.

AED 1,145 total

includes taxes & fees

8 Jul - 9 Jul

New Studio In Town, By the Water

Williamstown

Lydia J.

AED 1,137 total

includes taxes & fees

15 Jul - 16 Jul

Penthouse Apartment on Park Street

Adams

Margaret C.

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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you"

The Yankee Inn

10/10 Excellent

"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained."

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: Revitalized Firehouse Retreat in Downtown Shelburne Falls. Walk to Everything!: Located in Shelburne Falls, 16.8 mi/27 km from the heart of Windsor. Includes Smart TVs. Access to onsite laundry facilities is available on site. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located 21 mi/33.9 km away in Whitingham. Private balconies, fireplaces, and Smart TVs are included. Free breakfast and onsite laundry facilities are on site. New Studio In Town, By the Water: Located in Williamstown, 15.8 mi/25.5 km away. Includes free WiFi, private balconies, and sofa beds. Access to onsite laundry facilities is available on site. FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located 21.6 mi/34.8 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor 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 Skyline Trail.

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.

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Our top choices for Windsor apartments

2 Twin beds on 1st floor with En-suite bathroom.