Search Apartments in Windsor

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Apartments in Windsor

Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford
10.0 out of 10, Exceptional, (27)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is AED 251
AED 528 total
includes taxes & fees
17 Nov - 18 Nov
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is AED 496
AED 763 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
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 AED 323
AED 644 total
includes taxes & fees
19 Nov - 20 Nov
2 Twin beds on 1st floor with En-suite bathroom.
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...
United States
Teresa M.
The price is AED 426
AED 899 total
includes taxes & fees
17 Nov - 18 Nov
Penthouse Apartment on Park Street
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Indoor pool
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, (3)
"Great spot. Great communication. Comfortable suite."
United States
Samuel
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
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, (8)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
United States
Kevin K.
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
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
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Outdoor dining
2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water

Williamstown
9.6 out of 10, Exceptional, (11)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is AED 441
AED 991 total
includes taxes & fees
20 Nov - 21 Nov
2-Bdr Apt In Town, By the Water
Outdoor dining
Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops

Williamstown
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 477
AED 1,016 total
includes taxes & fees
20 Nov - 21 Nov
Downtown | Waterfront | Walk to Shops
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Our stay exceeded our expectations! The property is beautiful with a cute patio and modern furnishings/appliances. It had a homey and clean vibe and Dillon was nice enough to provide snacks, oatmeal, coffee, creamer, toothbrushes, etc. Everything we could need! We brought our two dogs and they seemed right at home and love going on walks through the fall leaves. Would definitely recommend for those with dogs, small children, or just traveling on their own!"
United States
Anja H.
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

New Studio In Town, By the Water

Williamstown
10.0 out of 10, Exceptional, (10)
"We loved our stay in Apt A! Easy to find, close to town and shops. The apartment was well equipped and stocked. The backyard space is a peaceful oasis. Listening to the river while relaxing in an Adirondack chair was exactly what my husband and I needed. It’s walking distance to the college campus and the Water St. Grill is right across the street! "
United States
Jay T.
The price is AED 441
AED 945 total
includes taxes & fees
20 Nov - 21 Nov
New Studio In Town, By the Water
3 bedrooms, iron/ironing board, WiFi, bed sheets
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
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is AED 1,273
AED 2,306 total
includes taxes & fees
17 Nov - 18 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior
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, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 580
AED 1,194 total
includes taxes & fees
17 Nov - 18 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior
Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath

Shelburne Falls
The price is AED 419
AED 759 total
includes taxes & fees
17 Nov - 18 Nov
Rose room Victorian home queen bed private bath
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Shelburne Falls
The price is AED 505
AED 946 total
includes taxes & fees
17 Nov - 18 Nov
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Exterior
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock
9.4 out of 10, Exceptional, (6)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock
10.0 out of 10, Exceptional, (3)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is AED 386
AED 866 total
includes taxes & fees
17 Nov - 18 Nov
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Outdoor dining
The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains

2.0 star property
North Adams
The price is AED 680
AED 1,190 total
includes taxes & fees
16 Dec - 17 Dec
The Allen House historic North Adams Home in the Berkshire Mountains
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 17.4 mi/28 km from the heart of Windsor. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor: Located in Hancock, 12.9 mi/20.7 km away. Includes sofa beds. A fitness center and an indoor pool are on site. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located 5.7 mi/9.2 km away in Dalton. Free WiFi, separate dining areas, and Smart TVs are included. 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 in Pownal, 21.6 mi/34.8 km from Windsor. Includes a private pool, free WiFi, and private patios. 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 Crane Museum of Papermaking and Mount Greylock State Reservation Visitor Center.
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.