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Our top choices for Windsor apartments

1. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is AED 413
AED 1,097 total
includes taxes & fees
17 Nov - 18 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Great penthouse apartment with interesting artwork throughout. Location convenient to local attractions; a five minutes easy drive to Mass MOCA. The apartment was impeccably clean and the host was very responsive to questions we had during our stay. Would love to stay again."
United States
Lisa M.
The price is AED 533
AED 976 total
includes taxes & fees
16 Nov - 17 Nov
Penthouse Apartment on Park Street

3. 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, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

4. 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, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

5. 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
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is AED 312
AED 710 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

6. 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, (14 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

7. 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 AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

8. 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, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

9. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

10. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

11. Relaxing 1-bedroom apartment in North Adams

Relaxing 1-bedroom apartment in North Adams
North Adams
The price is AED 463
AED 566 total
includes taxes & fees
16 Nov - 17 Nov
Relaxing 1-bedroom apartment in North Adams

12. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
New Studio In Town, By the Water

13. 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 338
AED 628 total
includes taxes & fees
16 Nov - 17 Nov
2 Twin beds on 1st floor with En-suite bathroom.

14. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is AED 303
AED 772 total
includes taxes & fees
16 Nov - 17 Nov
Berkshires Apartment at the Stephentown Hotel

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

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is AED 463
AED 1,001 total
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

16. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is AED 520
AED 1,060 total
includes taxes & fees
16 Nov - 17 Nov
Downtown | Waterfront | Walk to Shops

17. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (23 reviews)
"Perfect check in process, spotlessly clean, gorgeous property, and I wish I had had enough time to relax by the water. Best experience I've had, and I will definitely stay there again."
United States
Andrea
The price is AED 507
AED 1,067 total
includes taxes & fees
22 Nov - 23 Nov
2-Bdr Apt In Town, By the Water

18. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is AED 826
AED 1,116 total
includes taxes & fees
16 Nov - 17 Nov
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

19. 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
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is AED 354
AED 781 total
includes taxes & fees
16 Nov - 17 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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.

Top reviews in Windsor

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: 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 the heart of Windsor. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are on site. Downtown | Waterfront | Walk to Shops: Located 15.8 mi/25.5 km away in Williamstown. Free WiFi, private balconies, and sofa beds are included. A fitness center and onsite laundry facilities are on site. Cozy 1-bedroom apartment in old farm house in historic South Lee: Located in South Lee, 20.1 mi/32.3 km away. Includes private patios. Access to onsite laundry facilities is available on site. Quiet Neighborhood, For Bird Lovers: 21.2 mi/34.2 km away in South Deerfield.

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 Pontoosuc Lake.

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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