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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Windsor apartments

Exterior
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (28)
"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 248
AED 525 total
includes taxes & fees
9 Jan - 10 Jan
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Living area
Penthouse Apartment on Park Street

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AED 426
AED 899 total
includes taxes & fees
9 Jan - 10 Jan
Penthouse Apartment on Park Street
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is AED 323
AED 644 total
includes taxes & fees
11 Jan - 12 Jan
2 Twin beds on 1st floor with En-suite bathroom.
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Beach
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AED 491
AED 914 total
includes taxes & fees
11 Jan - 12 Jan
Berkshires Apartment at the Stephentown Hotel
Property grounds
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior
The Allen House historic North Adams Home in the Berkshire Mountains

Apartment in North Adams

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
10.0 out of 10, Exceptional, (1)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
The price is AED 643
AED 1,169 total
includes taxes & fees
9 Jan - 10 Jan
The Allen House historic North Adams Home in the Berkshire Mountains
Gift shop
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"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 AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Apartment in Hancock

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Private kitchen
Lenox Half Duplex

Apartment in Lee

Lenox Half Duplex
2.0 star property
The price is AED 555
AED 1,379 total
includes taxes & fees
9 Jan - 10 Jan
Lenox Half Duplex
Pool
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Fridge, microwave, stovetop, dishwasher
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Apartment in Whitingham

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is AED 1,600
AED 2,718 total
includes taxes & fees
13 Jan - 14 Jan
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Apartment in Shelburne Falls

Rose wisteria 4 guests 2 bedrooms-full+queen beds
The price is AED 545
AED 1,020 total
includes taxes & fees
11 Jan - 12 Jan
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Pool
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (31)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 775
AED 1,440 total
includes taxes & fees
15 Jan - 16 Jan
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beach
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Apartment in Stephentown

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
8.4 out of 10, Very Good, (12)
"Great location and property. thank you"
United States
Christine P.
The price is AED 559
AED 1,017 total
includes taxes & fees
11 Jan - 12 Jan
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Property grounds
2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment in Stephentown

2 Bed Berkshire Getaway @ Stephentown Hotel
10.0 out of 10, Exceptional, (5)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AED 648
AED 1,176 total
includes taxes & fees
11 Jan - 12 Jan
2 Bed Berkshire Getaway @ Stephentown Hotel
Indoor pool, a heated pool
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Apartment in Hancock

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
9.4 out of 10, Exceptional, (6)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Exterior
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Outdoor dining
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Apartment in Hancock

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

10/10 Excellent
"Really nice place staff "
Omayra 14-night trip
Posted 1 day ago
Red Roof Inn PLUS+ South Deerfield – Amherst

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: WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located in Hancock, 12.9 mi/20.8 km from the heart of Windsor. Includes sofa beds. A fitness center and onsite laundry facilities are on site. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located 12.8 mi/20.7 km away in Hancock. Fireplaces and sofa beds are included. A fitness center and onsite laundry facilities are on site. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake: Located in Whitingham, 21 mi/33.9 km away. Includes private balconies, fireplaces, and Smart TVs. Free breakfast and onsite laundry facilities are on site. Getaway Near Mass MoCA, Great Hiking, Scenic Views: Located 16.9 mi/27.1 km away in Stamford. Amenities include free WiFi. Access to onsite laundry facilities is available 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 Mount Greylock State Reservation Visitor Center. In the larger area, you'll find Skyline Trail 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.