Photo by William E Berry Jr.

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Browse Select Windsor Apartments

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is CA $210
CA $453 total
includes taxes & fees
Feb 11 - Feb 12
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"Everything was fantastic! Owner was amazing and so helpful and understanding. We had plenty of room as a family of 5 full over full bunk with full trundle - fireplace was great for ambiance. Ski on ski off so easy access gor a lunch break! Would definitely stay again."
Ski In/Out Studio at Okemo on Sachem Trail

Efficient condo near slopes with kitchenette & great location

9.2 out of 10, Wonderful, (26)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is CA $159
CA $362 total
includes taxes & fees
Feb 13 - Feb 14
Efficient condo near slopes with kitchenette & great location

Pleasant Street Retreat in Downtown Ludlow on Shuttle Route

Pleasant Street Retreat in Downtown Ludlow on Shuttle Route

Moose Tracks Lodge - Shuttle on and off, pool, hot tub

10.0 out of 10, Exceptional, (2)
"The whole process matched the personal touches and excellent nature of owners. Enjoyed it throughly. "
The price is CA $283
CA $989 total
includes taxes & fees
Feb 10 - Feb 11
Moose Tracks Lodge - Shuttle on and off, pool, hot tub

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

6.8 out of 10, (11)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is CA $138
CA $420 total
includes taxes & fees
Feb 6 - Feb 7
Riverfront studio with river view, full kitchen, & free WiFi

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

7.0 out of 10, Good, (2)
"Comfortable stay. Great location. Pool n spa was very nice and new."
The price is CA $359
CA $692 total
includes taxes & fees
Feb 5 - Feb 6
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

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

8.6 out of 10, Excellent, (10)
"This property was perfectly located across the street from a local shuttle (or a 5 min drive) to the ski resort and within walking distance to restaurants in town. The unit was clean and spacious. The guest services were easily available. The only minor downside was that the smart TV wouldn’t connect to WiFi - would recommend bringing a firestick or tablet. Would stay here again!"
The price is CA $328
CA $690 total
includes taxes & fees
Feb 3 - Feb 4
Remodeled condo with free WiFi & shared W/D - ski bus pickup across street

Condo near ski resorts with a private balcony & full kitchen

9.0 out of 10, Wonderful, (26)
"It was the best place and near all we ask for. the contraction was not quiet."
The price is CA $239
CA $754 total
includes taxes & fees
Feb 2 - Feb 3
Condo near ski resorts with a private balcony & full kitchen

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 $364
CA $678 total
includes taxes & fees
Feb 2 - Feb 3
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

9.2 out of 10, Wonderful, (10)
"Great stay. Close to okemo"
The price is CA $141
CA $440 total
includes taxes & fees
Feb 3 - Feb 4
Well-appointed studio right downtown - less than a mile to Okemo Mountain

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

9.8 out of 10, Exceptional, (164)
"Great central location for Okemo skiing. Okemo was super busy so MOOver was perfect and super easy and convenient for getting to/from mountain! Walkable to some great restaurants. Apartment had everything you need for your home away from home but DON’T FORGET TO BRING LINENS! "
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

2.0 star property
Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.

Classic Ski getaway in Killington!

Classic Ski getaway in Killington!

LilBear - Pool, Shuttle, Hot Tub, Gym

10.0 out of 10, Exceptional, (3)
"Great place. Kids loved the bunkbeds. Used the pool and sauna every day we were there. Beautiful view from porch. Thanks for everything! "
LilBear - Pool, Shuttle, Hot Tub, Gym

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (35)
"As we have Stayed here many times it is to die for to say as a getaway.. if you LOVE the true country Life getaway and are close to so much you must book this to understand .. Thank you once again Carol and DaveyStephen B"
Hawks Mountain Farm, full apartment on a working farm.

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (24)
"Conveniently located within a 5 min. drive to Okemo Mountain Resort and within walking distance of a number of restaurant/bars. Has all the necessities for a weekend in Ludlow."
The price is CA $147
CA $355 total
includes taxes & fees
Feb 5 - Feb 6
Cozy Studio Condo with Great Location, WiFi & Kitchenette

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 $1,947
CA $2,931 total
includes taxes & fees
Feb 5 - Feb 6
Modern Ski Château - 4 min from Killington Ski mountain lifts

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.0 out of 10, Wonderful, (2)
"I stayed at this condo with my partner and daughter for 3 nights in early Jan. Pros: clean, decent kitchen, comfortable couch and beds, fantastic location (1/2 mile from Snowshed and Ramshead). Cons: bedroom is very small and we weren’t really to use the closet because it contained the owner’s personal items. Very little counter space in bathroom. The condo needs more hooks for jackets and ski gear. Very nice stay."
The price is CA $224
CA $798 total
includes taxes & fees
Feb 3 - Feb 4
Wade's World Ski Home FirePlace Shuttle Location

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
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

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is CA $210
CA $453 total
includes taxes & fees
Feb 11 - Feb 12
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"Everything was fantastic! Owner was amazing and so helpful and understanding. We had plenty of room as a family of 5 full over full bunk with full trundle - fireplace was great for ambiance. Ski on ski off so easy access gor a lunch break! Would definitely stay again."
Ski In/Out Studio at Okemo on Sachem Trail

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
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 21 accommodations. 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?
Listed below are some of the favorite apartments in the area to choose from: Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.: Situated in Ludlow, 16.5 mi/26.5 km from the heart of Windsor. Includes free WiFi and Smart TVs. Ski In/Out Studio at Okemo on Sachem Trail: Located 18 mi/28.9 km away in Ludlow. Free WiFi, fireplaces, and sofa beds are included. Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located in Ludlow, 16.5 mi/26.6 km away. Includes private patios and sofa beds. Access to a spa tub is available on site. Efficient condo near slopes with kitchenette & great location: 17 mi/27.3 km away in Ludlow. Amenities include sofa beds. Riverfront studio with river view, full kitchen, & free WiFi: It’s situated in Cavendish, 14.3 mi/23 km from Windsor.
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 Brownsville Trail 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.