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12 Dec - 14 Dec
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30 Jan - 1 Feb

Apartments in Windsor

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

Apartment in Shelburne Falls

The price is SAR 248
SAR 566 total
includes taxes & fees
3 Dec - 4 Dec
2 Twin beds on 1st floor with En-suite bathroom.
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is SAR 507
SAR 779 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Apartment in Adams

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 SAR 435
SAR 918 total
includes taxes & fees
3 Dec - 4 Dec
Penthouse Apartment on Park Street
Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

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.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is SAR 394
SAR 885 total
includes taxes & fees
3 Dec - 4 Dec
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining
Downtown | Waterfront | Walk to Shops

Apartment in Williamstown

10.0 out of 10, Exceptional, (7)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is SAR 488
SAR 1,038 total
includes taxes & fees
14 Dec - 15 Dec
Downtown | Waterfront | Walk to Shops
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

Apartment in Williamstown

10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is SAR 450
SAR 966 total
includes taxes & fees
14 Dec - 15 Dec
New Studio In Town, By the Water
Outdoor dining
2-Bdr Apt In Town, By the Water

Apartment in 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 SAR 450
SAR 1,012 total
includes taxes & fees
14 Dec - 15 Dec
2-Bdr Apt In Town, By the Water
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

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 SAR 394
SAR 885 total
includes taxes & fees
3 Dec - 4 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Fridge, microwave, oven, stovetop
2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment in Stephentown

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 SAR 522
SAR 1,036 total
includes taxes & fees
3 Dec - 4 Dec
2 Bed Berkshire Getaway @ Stephentown Hotel
TV, DVD player, books
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

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 SAR 394
SAR 885 total
includes taxes & fees
3 Dec - 4 Dec
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in 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 SAR 394
SAR 885 total
includes taxes & fees
3 Dec - 4 Dec
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

Apartment in Hancock

9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Apartment in Shelburne Falls

The price is SAR 475
SAR 912 total
includes taxes & fees
3 Dec - 4 Dec
Rose wisteria 4 guests 2 bedrooms-full+queen beds
3 bedrooms, iron/ironing board, WiFi, bed sheets
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Apartment in Whitingham

10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is SAR 1,638
SAR 2,781 total
includes taxes & fees
3 Dec - 4 Dec
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Outdoor dining
The Allen House historic North Adams Home in the Berkshire Mountains

Apartment in North Adams

2.0 star property
The price is SAR 661
SAR 1,174 total
includes taxes & fees
7 Dec - 8 Dec
The Allen House historic North Adams Home in the Berkshire Mountains
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is SAR 507
SAR 779 total
includes taxes & fees
3 Dec - 4 Dec
Charming Apt in 18th c Berkshire Farmhouse
Exterior
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Apartment in Hancock

9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
United States
Alyne K.
The price is SAR 477
SAR 985 total
includes taxes & fees
23 Dec - 24 Dec
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

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 SAR 341
SAR 780 total
includes taxes & fees
3 Dec - 4 Dec
Berkshires Apartment at the Stephentown Hotel
Exterior
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Apartment in Hancock

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 SAR 394
SAR 885 total
includes taxes & fees
3 Dec - 4 Dec
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel

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: Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located in Hancock, 12.8 mi/20.7 km from the heart of Windsor. Includes fireplaces and sofa beds. A fitness center and onsite laundry facilities are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 17.4 mi/28 km away in Lee. Private patios and fireplaces 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 away. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are on site. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located 12.9 mi/20.8 km away in Hancock. Amenities include sofa beds. A fitness center and onsite laundry facilities are on site. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located in Hancock, 12.9 mi/20.7 km from Windsor. Includes fireplaces. A fitness center and a hot tub 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.