Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
Apr 18 - Apr 20
In two weeks
Apr 25 - Apr 27
In one month
May 9 - May 11
In two months
Jun 6 - Jun 8

Browse Select Windsor Apartments

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Internet, bed sheets

Cozy Studio Condo with Great Location, WiFi & Kitchenette

8.6 out of 10, Excellent, (25)
"Great location and great place!"
The price is CA $69
CA $264 total
includes taxes & fees
Apr 16 - Apr 17
Cozy Studio Condo with Great Location, WiFi & Kitchenette
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

9.2 out of 10, Wonderful, (27)
"Perfect location for a ski trip to Okemo! Very close to the mountain and shops in town. Hot tub was great!"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
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, (38)
"My husband and I love visiting Dave and Carol‘s place this time we got to meet all of the fun animals and enjoy fresh chicken, eggs, and goose egg! They are so welcoming and have a sweet little place to stay while we are skiing. We look forward to staying again."
Hawks Mountain Farm, full apartment on a working farm.
Efficient condo near slopes with kitchenette & great location
Property grounds

Efficient condo near slopes with kitchenette & great location

8.8 out of 10, Excellent, (30)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
The price is CA $69
CA $249 total
includes taxes & fees
Apr 21 - Apr 22
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

6.4 out of 10, (12)
"I have always had great experiences renting. this is my very first negative review. I am sorry i had to do this but others should be aware.The owner never communicated with me and never sent me the code to enter the property. I had to call VRBO/ Vacasa to complain. They were able to send me the code. When i got to the property it was clear that there was no effort made for my arrival. A few inches of snow had piled up in front of the entrance. There was also a very musty smell that hit me a...
The price is CA $78
CA $327 total
includes taxes & fees
Apr 12 - Apr 13
Riverfront studio with river view, full kitchen, & free WiFi
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, (170)
"It was a described. Well maintained, great communication."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Vermont Retreat
Fridge, microwave, oven, stovetop

Vermont Retreat

9.8 out of 10, Exceptional, (20)
"Everything was wonderful. There was excellent communication, the place was clean and had everything we needed for a weekend away. Ellen really personalizes the experience with special treats upon arrival and tips for places to eat. She even scraped off our jeep when we were heading out. Thank you Ellen! "
Vermont Retreat
Condo near ski resorts with a private balcony & full kitchen
Fridge, microwave, oven, stovetop

Condo near ski resorts with a private balcony & full kitchen

8.6 out of 10, Excellent, (27)
"It was the best place and near all we ask for. the contraction was not quiet."
Condo near ski resorts with a private balcony & full kitchen
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Property grounds

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 CA $69
CA $359 total
includes taxes & fees
Apr 12 - Apr 13
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.
Pool

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

8.8 out of 10, Excellent, (3)
"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
Microwave, oven, stovetop, coffee/tea maker

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
Smart TV, fireplace

Wade's World Ski Home FirePlace Shuttle Location

2.0 star property
9.6 out of 10, Exceptional, (5)
"We took a Spring snowboard up to Killington from Pennsylvania and had the joy of staying at Wades World. Coming off of our 6 hour drive to a home that was exactly as described was a huge relief. The check in process was as smooth as the spring snow we were carving on. The hosts were extremely responsive to my inquiries and very accommodating to my requests. I would absolutely stay here again! "
The price is CA $114
CA $473 total
includes taxes & fees
Apr 13 - Apr 14
Wade's World Ski Home FirePlace Shuttle Location
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.
Game room

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 CA $211
CA $306 total
includes taxes & fees
Apr 11 - Apr 12
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.
Aerial view

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 CA $110
CA $330 total
includes taxes & fees
Apr 13 - Apr 14
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Long Trail Suite | 10 Mins to Mountains | A/C
Aerial view

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

6.0 out of 10, (1)
The price is CA $114
CA $276 total
includes taxes & fees
Apr 29 - Apr 30
Long Trail Suite | 10 Mins to Mountains | A/C
Superb apartment in prime location - Ludlow centre just minutes from ski slopes
Exterior

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

9.8 out of 10, Exceptional, (50)
"Hard to beat the location with okemo shuttle stopping right out front and 1 block from downtown Ludlow for food and drink after a great day on the slopes!"
Superb apartment in prime location - Ludlow centre just minutes from ski slopes
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 $1,906
CA $2,875 total
includes taxes & fees
Apr 12 - Apr 13
Modern Ski Château - 4 min from Killington Ski mountain lifts
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
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.
Ski In/Out Studio at Okemo on Sachem Trail
Fridge, microwave, oven, stovetop

Ski In/Out Studio at Okemo on Sachem Trail

9.4 out of 10, Exceptional, (16)
"Incredible location - so easy to get on and off the slopes. The digital lock is a little wonky and we had some problems getting in sometimes but other than that had a great time!"
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
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is CA $306
CA $410 total
includes taxes & fees
Apr 13 - Apr 14
Mountain Green
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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 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: 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 hot tub is available on site. Cozy Studio Condo with Great Location, WiFi & Kitchenette: Located 17 mi/27.3 km away in Ludlow. Private patios and sofa beds are included. Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM: 22.9 mi/36.8 km away in Killington. Clean & bright condo with mountain views & modern kitchen - walk to lifts: Located in Killington, 22.9 mi/36.8 km from Windsor. Includes sofa beds. A fitness center and an indoor pool are 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 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.