Windsor Apartment Rentals from CA $255

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Windsor apartments

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

Shelburne Falls

CA $255 total

includes taxes & fees

Jul 6 - Jul 7

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

North Adams

CA $375 total

includes taxes & fees

Jul 7 - Jul 8

2-Bdr Apt In Town, By the Water

Williamstown

Dan R.

CA $398 total

includes taxes & fees

Jul 7 - Jul 8

Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

CA $416 total

includes taxes & fees

Jul 8 - Jul 9

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

Hancock

Jen B.

CA $431 total

includes taxes & fees

Jul 7 - Jul 8

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

Hancock

Neil J.

CA $419 total

includes taxes & fees

Jul 7 - Jul 8

New Studio In Town, By the Water

Williamstown

Lydia J.

CA $440 total

includes taxes & fees

Jul 15 - Jul 16

Penthouse Apartment on Park Street

Adams

Margaret C.

CA $395 total

includes taxes & fees

Jul 4 - Jul 5

View all properties

Find vacation rentals that suit your style

Cottages

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"It was generally excellent. The only difficultly I found was using the TV and that thermostat. A little too hi- tech"

Berkshire Mountain Lodge

8/10 Good

"The hotel was nice, full kitchen and quiet large for our family of four. We had a one bedroom suite, tucked into a corner of the hotel. Location was quiet, on the main floor. Pool and hot tub were nice. The sofa bed was not comfortable, at all. It would be worth the hotel replacing the sofa bed, as we could not sleep well at all and that is an important consideration for returning! One interesting thing that has nothing to do with the staff is that most of the other guests were older couples, and not particularly friendly or nice to staff or anyone else for that matter."

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."

Find out more about Windsor

Windsor Apartments information

Number of reviews	206
Accommodation	103 Apartments
Lowest Price	CA $255
Highest Price	CA $640

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.

Explore a world of travel with Expedia

Dalton Vacation Rentals

Book Apartments in Windsor on Expedia.com

Search Apartment Rentals in Windsor

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor apartments

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

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

2-Bdr Apt In Town, By the Water

Downtown | Waterfront | Walk to Shops

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

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

New Studio In Town, By the Water

Penthouse Apartment on Park Street

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Charming Apt in 18th c Berkshire Farmhouse

Rose room Victorian home queen bed private bath

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Rose wisteria 4 guests 2 bedrooms-full+queen beds

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Windsor

Windsor Apartments information

Frequently asked questions

Explore a world of travel with Expedia