Photo by William E Berry Jr.

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Compare 131 Apartments in Windsor with updated reviews, rates, and availability.

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (27)
"Perfect spot to stay for a ski weekend at Okemo. It’s literally down the block. Can’t say enough great things about the room. Clean, comfortable, safe. It had everything I needed. "
The price is AED 180
AED 684 total
includes taxes & fees
4 May - 5 May
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.2 out of 10, Wonderful, (26)
"Perfect for families to interact and experience the beautiful nature of Vermont highly recommend this location"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (38)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.

Efficient condo near slopes with kitchenette & great location

8.8 out of 10, Excellent, (30)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
Efficient condo near slopes with kitchenette & great location

Riverfront studio with river view, full kitchen, & free WiFi

6.8 out of 10, (11)
"Easy to find, somewhat dated but clean and tidy, comfortable bed; perfect for a short stay."
The price is AED 202
AED 766 total
includes taxes & fees
3 May - 4 May
Riverfront studio with river view, full kitchen, & free WiFi

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

9.8 out of 10, Exceptional, (170)
"It was a described. Well maintained, great communication."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Vermont Retreat

9.8 out of 10, Exceptional, (20)
"We thoroughly enjoyed our stay. It was the perfect location between events that we were attending. Beautiful location, wonderful house and attentive/ helpful hosts."
Vermont Retreat

Condo near ski resorts with a private balcony & full kitchen

8.6 out of 10, Excellent, (27)
"Excellent location, condo in great condition. "
Condo near ski resorts with a private balcony & full kitchen

Clean & bright condo with mountain views & modern kitchen - walk to lifts

7.4 out of 10, Good, (43)
"Quick trip to and from Killington mt"
The price is AED 217
AED 934 total
includes taxes & fees
5 May - 6 May
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Pinnacle F21, 3 bedroom 2 bath with shuttle to the slopes every day of the week.

9.0 out of 10, Wonderful, (4)
"The unit was exactly as advertised. Slept 4 adults and 3 children comfortably. Killington is very close and Pico is about a 15 minute ride. Would stay again. Thank you."
Pinnacle F21, 3 bedroom 2 bath with shuttle to the slopes every day of the week.

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.6 out of 10, Exceptional, (5)
"This space was perfect for my wife and I as we explored Vermont. Its relative proximity to Woodstock made it an ideal stay for a few days while enjoyed everything the area had to offer. The owner’s instructions for check-in and check-out were simple and clear. It was very clean and orderly, but homely and comfortable."
The price is AED 298
AED 1,224 total
includes taxes & fees
4 May - 5 May
Wade's World Ski Home FirePlace Shuttle Location

Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.

10.0 out of 10, Exceptional, (1)
"Close to Okemo, property is fun, and owner is respectful/great communication. "
The price is AED 709
AED 1,004 total
includes taxes & fees
5 May - 6 May
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

8.0 out of 10, Very Good, (2)
"Room was great for the 140 price point it normally is, not the 250 price for World Cup weekend. Would stay again though, very convenient. Checkin was super easy and the room was clean, just needs "
The price is AED 287
AED 813 total
includes taxes & fees
4 May - 5 May
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

Long Trail Suite | 10 Mins to Mountains | A/C

6.0 out of 10, (1)
The price is AED 290
AED 703 total
includes taxes & fees
6 May - 7 May
Long Trail Suite | 10 Mins to Mountains | A/C

Superb apartment in prime location - Ludlow centre just minutes from ski slopes

9.8 out of 10, Exceptional, (50)
"The place was clean and well equipped with everything you need. Great location to the mountain, ski bus, and restaurants. Ian was a great host."
Superb apartment in prime location - Ludlow centre just minutes from ski slopes

Modern Ski Château - 4 min from Killington Ski mountain lifts

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay- it was perfect for our family of 4. Easy access to Killington and Pico and the pool was a great bonus for the kids!"
The price is AED 4,966
AED 7,475 total
includes taxes & fees
9 May - 10 May
Modern Ski Château - 4 min from Killington Ski mountain lifts

2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House

9.0 out of 10, Wonderful, (8)
"We enjoyed our stay! Stephen was very nice just a message away if we needed anything. "
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House

Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.

9.6 out of 10, Exceptional, (14)
"Bob was an incredible host and very responsive! This was a perfect getaway for me and the property was great. I'd stay again in a heartbeat. Thanks Bob for the great stay!"
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.

Ski In/Out Studio at Okemo on Sachem Trail

9.4 out of 10, Exceptional, (16)
"Great location, appliances, very clean"
Ski In/Out Studio at Okemo on Sachem Trail
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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"We had a wonderful long weekend stay at the cottage on Crescent Lake! The place has all of the amenities that you need for a relaxing and fun filled time on the lake. We will definitely be back for another stay next year!"
Cozy Crescent Cottage

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AED 624
AED 1,345 total
includes taxes & fees
5 May - 6 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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’ll find 19 accommodations in Windsor. Though there aren’t many apartments, we can help you find accommodations that are similar. 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 also filter by similar properties such as vacation homes, condos, or guest houses.
How do you know if an apartment is a good option for you?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families who want the conveniences of home.
What's a favorite apartment I should consider for a stay in Windsor?
Below are some of the favorite apartments in the area: Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located 16.5 mi/26.6 km away in Ludlow. Private patios and sofa beds are included. Access to a hot tub is available on site. Clean & bright condo with mountain views & modern kitchen - walk to lifts: Located in Killington, 22.9 mi/36.8 km away. Includes sofa beds. A fitness center and onsite laundry facilities are on site. Efficient condo near slopes with kitchenette & great location: 17 mi/27.3 km away in Ludlow. Amenities include 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 if you are planning a longer stay in Windsor. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.
What are the must-see places to visit in Windsor?
Connecticut River and Paradise Park are a couple of scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. While here, Harpoon Brewery and Mt Ascutney State Park are other places worth a visit.
What's the best way to get to and around Windsor?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) from the heart of the city. Otherwise, look for flights into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. To venture out into the surrounding area, hop aboard a train at Windsor Station.