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Our top choices for Windsor apartments

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

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is CA $131
CA $255 total
includes taxes & fees
Jul 6 - Jul 7
2 Twin beds on 1st floor with En-suite bathroom.

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

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is CA $202
CA $375 total
includes taxes & fees
Jul 7 - Jul 8
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is CA $170
CA $398 total
includes taxes & fees
Jul 7 - Jul 8
2-Bdr Apt In Town, By the Water

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is CA $192
CA $416 total
includes taxes & fees
Jul 8 - Jul 9
Downtown | Waterfront | Walk to Shops

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

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is CA $226
CA $431 total
includes taxes & fees
Jul 7 - Jul 8
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

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is CA $216
CA $419 total
includes taxes & fees
Jul 7 - Jul 8
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (13 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $213
CA $440 total
includes taxes & fees
Jul 15 - Jul 16
New Studio In Town, By the Water

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is CA $206
CA $395 total
includes taxes & fees
Jul 4 - Jul 5
Penthouse Apartment on Park Street

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
The price is CA $192
CA $292 total
includes taxes & fees
Jul 16 - Jul 17
Charming Apt in 18th c Berkshire Farmhouse

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $150
CA $277 total
includes taxes & fees
Jul 6 - Jul 7
Rose room Victorian home queen bed private bath

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

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $216
CA $419 total
includes taxes & fees
Jul 7 - Jul 8
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

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is CA $227
CA $433 total
includes taxes & fees
Jul 7 - Jul 8
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is CA $230
CA $436 total
includes taxes & fees
Jul 6 - Jul 7
Rose wisteria 4 guests 2 bedrooms-full+queen beds

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

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is CA $216
CA $419 total
includes taxes & fees
Jul 7 - Jul 8
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is CA $315
CA $582 total
includes taxes & fees
Jul 7 - Jul 8
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

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"Host very responsive. I gave feedback that could make stay better like more hangars and some coat hooks. Massage chair in unit was a hit with the whole family.Unit is literally the last unit in last builing of Coubtry Inn away from ski school and Express lift. Still walkable, just not in ski boots.Parking in front of unit super easy.No elevator nearby. Upstairs with luggage. "
United States
Joe C.
The price is CA $215
CA $418 total
includes taxes & fees
Jul 7 - Jul 8
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

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (6 reviews)
"Gorgeous views even in March, ample heating/cooling, wonderful host experience, would just recommend bringing paper plates/utensils as we found ourselves running the dishwasher often. "
United States
avery o.
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

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is CA $216
CA $419 total
includes taxes & fees
Jul 7 - Jul 8
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

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
The price is CA $317
CA $640 total
includes taxes & fees
Jul 7 - Jul 8
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
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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Top Windsor Hotel Reviews

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.

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