Best Apartments in Windsor, MA for Your Vacation from $68

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Our top choices for Windsor apartments

Coffee/tea maker, fridge, microwave, oven

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

Dalton

Megan A.

$293 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Penthouse Apartment on Park Street

Adams

Margaret C.

$252 nightly

Aug 20 - Aug 21

Total with taxes and fees

3. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Hancock

Alicia S.

$211 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

Hancock

Jen B.

$216 nightly

Aug 19 - Aug 20

Total with taxes and fees

5. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

$132 nightly

Aug 19 - Aug 20

Total with taxes and fees

6. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock

John F.

$199 nightly

Aug 19 - Aug 20

Total with taxes and fees

7. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

$211 nightly

Aug 18 - Aug 19

Total with taxes and fees

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

Tom C.

$206 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

Hancock

patricia f.

$234 nightly

Aug 20 - Aug 21

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi

10. Balcony Room in Victorian Home private bath

Shelburne Falls

$183 nightly

Sep 13 - Sep 14

Total with taxes and fees

11. New Studio In Town, By the Water

Williamstown

Lydia J.

$240 nightly

Aug 19 - Aug 20

Total with taxes and fees

12. 2-Bdr Apt In Town, By the Water

Williamstown

Dan R.

$263 nightly

Aug 19 - Aug 20

Total with taxes and fees

13. Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

$263 nightly

Aug 31 - Sep 1

Total with taxes and fees

14. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Hancock

Todd A.

$298 nightly

Aug 18 - Aug 19

Total with taxes and fees

15. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Hancock

Matthew B.

$216 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

Hancock

"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...

Cecilia S.

$302 nightly

Aug 18 - Aug 19

Total with taxes and fees

17. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

$256 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

Hancock

Kristina L.

$211 nightly

Aug 18 - Aug 19

Total with taxes and fees

19. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Hancock

Alyne K.

$211 nightly

Aug 18 - Aug 19

Total with taxes and fees

20. Spacious & Cozy Ground Floor 2/3 Bed private suite

Shelburne Falls

Russ D.

$385 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Windsor Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Place was clean and well equipped, pool and amenities were great too !"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"The location just off busy route 20 was a minus, especially since it is difficult to make a left hand turn out of the property with the heavy traffic. The hotel itself was clean, modern and comfortable. All staff were friendly and helpful. The breakfast was generous and well prepared/presented. We enjoyed the pool, hot tub and the exercise room."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The location was excellent, and the roads between Lee and Stockbridge, and in a lovely, secluded area. The rooms were spacious, ours included a living room, dining and kitchen area, and upstairs bedroom with spacious closet and bathroom. The price was reasonable. It was very quiet and well maintained. There was a lot for kids to do -- swimming pool and movies. We would go there again."

Find out more about Windsor

Windsor Apartments information

Number of reviews	8,136
Accommodation	97 Apartments
Lowest Price	$68
Highest Price	$200

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: Getaway Near Mass MoCA, Great Hiking, Scenic Views: Located in Stamford, 16.9 mi/27.1 km from the heart of Windsor. Includes free WiFi. 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. 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. 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. 2-Bdr Apt In Town, By the Water: Located in Williamstown, 15.8 mi/25.5 km from Windsor. Includes 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 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.

Apartments in Windsor for Rent

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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

2. Penthouse Apartment on Park Street

3. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

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

5. Getaway Near Mass MoCA, Great Hiking, Scenic Views

6. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

7. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

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

10. Balcony Room in Victorian Home private bath

11. New Studio In Town, By the Water

12. 2-Bdr Apt In Town, By the Water

13. Downtown | Waterfront | Walk to Shops

14. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

15. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

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

17. Berkshires Apartment at the Stephentown Hotel

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

19. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

20. Spacious & Cozy Ground Floor 2/3 Bed private suite

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Find out more about Windsor

Windsor Apartments information

Frequently asked questions

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