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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Apartments in Windsor

Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.6 out of 10, Exceptional, (11)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
The price is AED 551
AED 1,050 total
includes taxes & fees
26 Oct - 27 Oct
Park Street Penthouse Apartment
51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (33)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit
Charming 1-BR Apartment in Conway, WiFi/AC
Terrace/patio

Charming 1-BR Apartment in Conway, WiFi/AC

10.0 out of 10, Exceptional, (1)
"I rented this property for a ski week end. The place is beautifully decorated, very spacious and fully equipped. Located 30min from berkshire east mountain, it was a perfect choice."
Charming 1-BR Apartment in Conway, WiFi/AC
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.
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)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
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, (68)
"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
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
Downtown | Waterfront | Walk to Shops
Outdoor dining

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
The price is AED 477
AED 1,012 total
includes taxes & fees
23 Oct - 24 Oct
Downtown | Waterfront | Walk to Shops
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (30)
"We really enjoyed our stay it was a very nice place for a family."
The price is AED 577
AED 1,190 total
includes taxes & fees
6 Oct - 7 Oct
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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, (3)
"Great property and location for a visit to Shelburne Falls. "
The price is AED 586
AED 1,315 total
includes taxes & fees
5 Oct - 6 Oct
Spacious & Cozy Ground Floor 2/3 Bed private suite
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 AED 441
AED 941 total
includes taxes & fees
8 Oct - 9 Oct
New Studio In Town, By the Water
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. "
The price is AED 408
AED 890 total
includes taxes & fees
6 Oct - 7 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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
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
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 AED 1,414
AED 2,481 total
includes taxes & fees
2 Nov - 3 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (9)
"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
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Fridge, microwave, oven, stovetop

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (46)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (12)
"My husband and I and our little dog had an amazing stay in Dalton. The space was clean, perfectly decorated and comfortable! We only stayed a few days and wanted to stay so much longer! Coffee for the humans and frog toys and treats for Sully! Very convenient to all the Berkshires has to offer. Communication with the owner was prompt and always helpful!! Highly recommend and hope to return. "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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 AED 415
AED 903 total
includes taxes & fees
7 Oct - 8 Oct
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Exterior

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

10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 2 days ago
The Red Lion Inn

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. Cozy Rustic Apt in 18th c Berkshire Farmhouse: Located 9.6 mi/15.5 km away in Lanesborough. Fireplaces and sofa beds are included. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located 5.7 mi/9.2 km away in Dalton. Free WiFi, separate dining areas, and Smart TVs are included. 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 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.