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Compare 77 Apartments in Windsor with updated reviews, rates, and availability.

Lovely two bedroom river-view rental unit
Property grounds
Lovely two bedroom river-view rental unit
9.2 out of 10, Wonderful, (19)
"Typical New England older home. 2nd floor unit. Comfy beds, well-stocked kitchen (that did remind me a bit of my first place out of college). This is definitely not The Ritz, but the linens were soft and the place worked for us."
The price is SAR 563
SAR 1,196 total
includes taxes & fees
16 Dec - 17 Dec
Lovely two bedroom river-view rental unit
Park Street Penthouse Apartment
Private kitchen
Park Street Penthouse Apartment
9.0 out of 10, Wonderful, (2)
"Like exploring new areas. Quaint town with a few restaurants and a diner in walking distance. Huge apt - well more than needed for one night … clean and has everything you would need to stay longer including laundry and full kitchen. Little hot bc only has window AC units as it’s an old art deco building. Close driving to my resorts and things to do in zbershired"
The price is SAR 732
SAR 1,296 total
includes taxes & fees
16 Dec - 17 Dec
Park Street Penthouse Apartment
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Interior
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
2.0 star property
10.0 out of 10, Exceptional, (3)
"The property was clean, well equipped, and very comfortable. We had ample parking for our car and our son's car right outside the door, with room for our other son to park when he visited us. It is beautifully decorated with paintings and art objects, many with an Asian theme. It's close to the Shelburne Falls village and to Route 2 for touring the area, but it was very quiet at night, lending itself to very restful sleeps over night. Host was very available and helpful! Hope to stay there...
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Charming Apartment In Berkshire Victorian Home
Exterior
Charming Apartment In Berkshire Victorian Home
7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (20)
"the owner was very nice and helpfull"
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
2-Bdr Apt In Town, By the Water
Private kitchen
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (3)
"Lovely property, in good shape. Close to many Williamstown attractions."
The price is SAR 451
SAR 925 total
includes taxes & fees
17 Nov - 18 Nov
2-Bdr Apt In Town, By the Water
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Living area
Private 1-bedroom apartment in enchanting North Adams with WiFi.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Dianne was great and accommodating. Check in was so easy and the apartment was more spacious than expected! Very clean, neat, and organized. She made our stay at North Adams welcoming and would definitely book again. Thank you so much! "
The price is SAR 616
SAR 956 total
includes taxes & fees
16 Dec - 17 Dec
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is SAR 545
SAR 815 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Private apartment in beautiful country barn
Living area
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
New Studio In Town, By the Water
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)
New Studio In Town, By the Water
10.0 out of 10, Exceptional, (3)
"Great location"
The price is SAR 451
SAR 879 total
includes taxes & fees
18 Nov - 19 Nov
New Studio In Town, By the Water
Vacation Rental Home in the Berkshires!
Williamstown Vacation Rental | Studio | 1BA | Stairs Required | 1,000 Sq Ft
Vacation Rental Home in the Berkshires!
9.6 out of 10, Exceptional, (10)
"Beautiful property, amazing views, lots of privacy, home is nicely decorated and had everything we needed and more. Will definitely visit again!"
Vacation Rental Home in the Berkshires!
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.2 out of 10, Wonderful, (9)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is SAR 391
SAR 847 total
includes taxes & fees
17 Nov - 18 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Main Street Delight 1bedroom
Living area
Main Street Delight 1bedroom
10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
Private kitchen
Heart of Lenox!! - renovated downtown apartment
10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Comfortable Living Room with Pullout Queen Sofa Bed and Smart TV with Full DVD Library and Board Game library for those nights in.
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is SAR 391
SAR 847 total
includes taxes & fees
17 Nov - 18 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Vacation Rental Home in the Berkshires!
Living area
Vacation Rental Home in the Berkshires!
3.0 star property
Vacation Rental Home in the Berkshires!
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Fully Redone Suite with master King Bed
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is SAR 391
SAR 847 total
includes taxes & fees
17 Nov - 18 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gateway to the Berkshires - Renovated downtown apartment
Room
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
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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Other property types in Windsor

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is SAR 634
SAR 733 total
includes taxes & fees
25 Nov - 26 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is SAR 560
SAR 614 total
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.

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: Lovely two bedroom river-view rental unit: Situated in Williamstown, 17 mi/27.3 km from the heart of Windsor. Includes sofa beds. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: Located 17 mi/27.3 km away in Richmond. New Studio In Town, By the Water: It’s situated in Williamstown, 15.8 mi/25.5 km away. Includes free WiFi, private balconies, and sofa beds. Downtown | Waterfront | Walk to Shops: Located in Williamstown, 15.8 mi/25.5 km from Windsor. Includes free WiFi, private balconies, and sofa beds. Access to a fitness center 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 Savoy Mountain State Forest. In the larger area, you’ll find Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest.
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.