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

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

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

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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 AED 551
AED 1,169 total
includes taxes & fees
2 Dec - 3 Dec
Lovely two bedroom river-view rental unit
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)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
The price is AED 577
AED 1,170 total
includes taxes & fees
19 Dec - 20 Dec
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Super comfortable Mountain Decor

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

10.0 out of 10, Exceptional, (22)
"We loved our stay. The rental was as described. Jiminy Peak is great and everything is within walking distance. We had a great time !!!"
The price is AED 382
AED 835 total
includes taxes & fees
1 Dec - 2 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi
Living area

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi
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 AED 533
AED 797 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

10.0 out of 10, Exceptional, (6)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely 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 AED 441
AED 863 total
includes taxes & fees
30 Nov - 1 Dec
New Studio In Town, By the Water
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 AED 382
AED 835 total
includes taxes & fees
28 Nov - 29 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
Vacation Rental Home in the Berkshires!
Living area

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
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.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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!
Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
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
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (30)
"Some friends and I were in town for a wedding and were just staying the night and the property was perfect for what we needed! It was very clean and well-maintained. The only minor thing was the building is close to the road and we could hear some traffic at night, but it wasn’t too disruptive. We really enjoyed our stay, thank you!"
The price is AED 533
AED 797 total
includes taxes & fees
28 Nov - 29 Nov
Charming Apt in 18th c Berkshire Farmhouse
Quiet Neighborhood, For Bird Lovers
Property grounds

Quiet Neighborhood, For Bird Lovers

10.0 out of 10, Exceptional, (45)
"We stayed here while visiting our daughter, a student at UMass-Amherst, last year and liked it so much, we stayed again this year. Lovely place! Quiet neighborhood, great host (who even leaves fresh food staples in the fridge for her guests), very clean and well maintained. Two thumbs up!"
Quiet Neighborhood, For Bird Lovers
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)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
1 Dec - 2 Dec
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, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 657
AED 721 total
includes taxes & fees
28 Nov - 29 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 more popular apartments in the area to choose from: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Situated in Lee, 17.4 mi/28 km from the heart of Windsor. Includes private patios and fireplaces. Lovely two bedroom river-view rental unit: 17 mi/27.3 km away in Williamstown. Amenities include sofa beds. Cozy Rustic Apt in 18th c Berkshire Farmhouse: It’s located in Lanesborough, 9.6 mi/15.5 km from Windsor. Includes fireplaces and sofa beds.
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.