Photo by William E Berry Jr.

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Browse Select Windsor Apartments

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Living area

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

The price is CA $357
CA $685 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Efficient condo near slopes with kitchenette & great location
Property grounds

Efficient condo near slopes with kitchenette & great location

9.0 out of 10, Wonderful, (24)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
The price is CA $123
CA $311 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Efficient condo near slopes with kitchenette & great location
Riverfront studio with river view, full kitchen, & free WiFi
Fridge, microwave, oven, stovetop

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

7.2 out of 10, Good, (10)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is CA $128
CA $405 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Riverfront studio with river view, full kitchen, & free WiFi
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is CA $363
CA $705 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Fridge, microwave, oven, coffee/tea maker

Well-appointed studio right downtown - less than a mile to Okemo Mountain

9.2 out of 10, Wonderful, (10)
"Great stay. Close to okemo"
The price is CA $141
CA $440 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

9.8 out of 10, Exceptional, (17)
"Cozy and everything you could need. Really nice kitchen set up and excellent appliances. After a week on the road, the washer & dryer were a welcome refresh of clothing. It's a few minutes west of Woodstock down a country road, so secluded. Takes dogs - wish we had one!"
Vermont Retreat
Hawks Mountain Farm, full apartment on a working farm.
Property grounds

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (32)
"Place was quiet, quaint and comfortable. Host was very friendly making it a great stay. "
Hawks Mountain Farm, full apartment on a working farm.
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Outdoor dining

Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily

9.2 out of 10, Wonderful, (15)
"Great price, location, and property owner. "
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
BearPaw- Shuttle to slopes, pool, hot tub, sauna
Aerial view

BearPaw- Shuttle to slopes, pool, hot tub, sauna

The price is CA $445
CA $943 total
includes taxes & fees
Jan 1 - Jan 2, 2025
BearPaw- Shuttle to slopes, pool, hot tub, sauna
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Fridge, microwave, oven, stovetop

Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

8.6 out of 10, Excellent, (9)
"Property was cozy and comfortable! Definitely would not be able to fit more than 4 as when the sofa bed is expanded, the "living room" floor space is basically full. Showers and amenities were great, but they did not have a pan in case you were planning on cooking. Also price was pretty high for 1 night, but presumably cleaning fees would be cheaper when split over more nights."
The price is CA $327
CA $689 total
includes taxes & fees
Dec 30 - Dec 31
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Indoor pool

Spacious mountain studio with free WiFi & full kitchen - close to skiing

6.0 out of 10, (18)
"Communication was excellent and service was great."
The price is CA $184
CA $506 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Run, ride, hike and swim in Central Vermont
Fridge, microwave, oven, stovetop

Run, ride, hike and swim in Central Vermont

9.8 out of 10, Exceptional, (14)
"This was a nice quiet place to stay! I was in the area for a class and needed a place to stay. It was clean and comfy"
Run, ride, hike and swim in Central Vermont
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

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

9.8 out of 10, Exceptional, (163)
"Bob has always been easy to communicate with and we love the cozy yes spacious stay. Highly recommend!"
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
Exterior

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

9.6 out of 10, Exceptional, (15)
"We enjoyed staying upstairs and all the room that the apartment has. We remembered to bring our own sheets & towels and everything else we needed was in the apartment. Robert is very friendly and helpful. "
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
BearHug - HotTub Fireplace shuttle on ski home
Indoor pool, a heated pool

BearHug - HotTub Fireplace shuttle on ski home

10.0 out of 10, Exceptional, (4)
"Exactly as advertised. Immaculate. Great communication. Comfy bed!"
The price is CA $606
CA $1,271 total
includes taxes & fees
Jan 8 - Jan 9, 2025
BearHug - HotTub Fireplace shuttle on ski home
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (7)
"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
Modern Ski Château - 4 min from Killington Ski mountain lifts
Fridge, oven, stovetop, dishwasher

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 CA $1,941
CA $2,941 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Modern Ski Château - 4 min from Killington Ski mountain lifts
8 Mi to Okemo Mtn: Charming Ludlow Studio!
Interior

8 Mi to Okemo Mtn: Charming Ludlow Studio!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I decided to stay a bit out of town for a ski trip....and it was perfect. Just a 10 min ride down the hill to OKEMO and LUDLOW. It is absolutely beautiful and quiet...the sunsets and sunrises are amazing from the top of that hill. It is secluded and you really get a slice of VT. The unit is very large and spacious. It has everything you need for a short stay...for some, not having a microwave is an issue, but not for me. Toaster over, full stove, fridge, electric water kettle, coffee maker,...
8 Mi to Okemo Mtn: Charming Ludlow Studio!
SnowDen - Ski on and off at Pico, Fireplace
Fridge, microwave, oven, stovetop

SnowDen - Ski on and off at Pico, Fireplace

The price is CA $423
CA $1,039 total
includes taxes & fees
Jan 6 - Jan 7, 2025
SnowDen - Ski on and off at Pico, Fireplace
Pinnacle C16
Condo, 1 King Bed (Pinnacle C16) | Aerial view

Pinnacle C16

3.0 star property
8.0 out of 10, Very good, (2)
Pinnacle C16
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
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Beautiful Myrtle Beach Condo with Amenities Galore
Beach nearby

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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?
There are plenty of places to stay in Windsor with 20 hotels and other accommodations. Though there aren’t many apartments, we can help you search for 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 such as a kitchen. You can also filter by similar properties such as vacation homes, condos, or cabins. Make time to visit the region’s favorite places like Okemo Mountain Resort.
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?
Listed below are some of the favorite apartments in the area to choose from: Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located in Ludlow, 16.5 mi/26.6 km from the heart of Windsor. Includes private patios and sofa beds. Access to a spa tub is available on site. Efficient condo near slopes with kitchenette & great location: Located 17 mi/27.3 km away in Ludlow. Amenities include sofa beds. Riverfront studio with river view, full kitchen, & free WiFi: It’s located in Cavendish, 14.3 mi/23 km away. Well-appointed studio right downtown - less than a mile to Okemo Mountain: 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?
Mt Ascutney State Park and Connecticut River 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 South Congregational Church 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.