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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Apartments in Windsor

Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (10)
"The penthouse was beautiful and spacious. The Host Lea was very congenial and offered great suggestions for the location. I will definitely be coming back "
The price is SAR 371
SAR 834 total
includes taxes & fees
2 Sep - 3 Sep
Park Street Penthouse Apartment
Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.4 out of 10, Exceptional, (35)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is SAR 507
SAR 779 total
includes taxes & fees
4 Sep - 5 Sep
Charming Apt in 18th c Berkshire Farmhouse
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (66)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.6 out of 10, Exceptional, (4)
"Great place. Exactly as described."
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very Good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
Downtown | Waterfront | Walk to Shops
Outdoor dining

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (5)
"Beautiful property and wonderful hosts. Terrific location."
The price is SAR 488
SAR 1,038 total
includes taxes & fees
2 Sep - 3 Sep
Downtown | Waterfront | Walk to Shops
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is SAR 507
SAR 762 total
includes taxes & fees
2 Sep - 3 Sep
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
New Studio In Town, By the Water
Fridge, microwave, oven, stovetop

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (7)
"Great location, we really enjoyed our stay! "
The price is SAR 450
SAR 966 total
includes taxes & fees
2 Sep - 3 Sep
New Studio In Town, By the Water
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.6 out of 10, Exceptional, (8)
"The apartment was clean, bright and quiet. Comfortable beds, and well equipped kitchen. About 3 minute walk to shops on spring street and a nice spot out back by the Green river. Perfect spot for a visit to Williamstown! "
The price is SAR 450
SAR 1,013 total
includes taxes & fees
2 Sep - 3 Sep
2-Bdr Apt In Town, By the Water
Spacious & Cozy Ground Floor 2/3 Bed private suite
Property grounds

Spacious & Cozy Ground Floor 2/3 Bed private suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property and location for a visit to Shelburne Falls. "
The price is SAR 544
SAR 1,278 total
includes taxes & fees
2 Sep - 3 Sep
Spacious & Cozy Ground Floor 2/3 Bed private suite
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior

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

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

9.8 out of 10, Exceptional, (18)
"Lovely cottage with beautiful views"
Vacation Rental Home in the Berkshires!
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
The Penthouse, Downtown Lenox by Evergreen Home
Fridge, microwave, oven, stovetop

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (10)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

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

10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is SAR 1,300
SAR 2,381 total
includes taxes & fees
10 Sep - 11 Sep
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
TV, DVD player, books

Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain

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!!"
The price is SAR 390
SAR 876 total
includes taxes & fees
3 Sep - 4 Sep
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
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

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: Park Street Penthouse Apartment: Located in Adams, 8.7 mi/14 km from the heart of Windsor. Includes sofa beds. 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 21.6 mi/34.8 km away in Pownal. A private pool, free WiFi, and private patios are included. Onsite laundry facilities and an outdoor pool are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 17.4 mi/28 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Charming Apt in 18th c Berkshire Farmhouse: Located 9.6 mi/15.5 km away in Lanesborough. Amenities include fireplaces. Access to onsite laundry facilities is available on site. Downtown | Waterfront | Walk to Shops: Located in Williamstown, 15.8 mi/25.5 km from Windsor. Includes free WiFi, private balconies, and sofa beds. A fitness center and onsite laundry facilities 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 Mount Greylock State Reservation Visitor Center. In the larger area, you'll find Mount Greylock and Barrington Stage Company.
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.