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Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

Browse Select Windsor Apartments

Hawks Mountain Farm, full apartment on a working farm.
Stroll through the beautifully maintained garden, surrounded by lush trees and a variety of plants.

Hawks Mountain Farm, full apartment on a working farm.

9.8 out of 10, Exceptional, (40)
"Very nice place "
Hawks Mountain Farm, full apartment on a working farm.
Nana's House
Stroll through a beautifully maintained garden featuring a variety of flowering shrubs.

Nana's House

10.0 out of 10, Exceptional, (39)
"I'm not much for reviews, but everything about this place was perfect! We can't wait to go back!"
Nana's House
Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi
Enjoy cooking in this well-equipped kitchen with a central island, sink, stainless steel stove, and oven.

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

Spacious studio, dog-friendly, close to recreation, central a/c, TV, wifi
Condo near ski resorts with a private balcony & full kitchen
Fully equipped kitchen with stainless steel appliances, wooden cabinetry, and a tiled backsplash.

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
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Enjoy cooking in this well-equipped kitchen with a microwave, dishwasher, and stainless steel sink.

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

8.8 out of 10, Excellent, (29)
"We had a great time here and would definitely stay again!"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Enjoy meals at the dining table, surrounded by stainless steel appliances and a decorative wall piece.

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

9.8 out of 10, Exceptional, (67)
"A weekend trip to visit the area and get away was perfect!"
The price is CA $130
CA $433 total
includes taxes & fees
Aug 5 - Aug 6
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and dishwasher.

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

9.0 out of 10, Wonderful, (8)
"Had everything that is needed and easy to get to."
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Long Trail Suite | 10 Mins to Mountains | A/C
Escape to a serene retreat surrounded by lush greenery and a dense forest, with a spacious porch and deck.

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

6.0 out of 10, (1)
The price is CA $110
CA $267 total
includes taxes & fees
Jul 15 - Jul 16
Long Trail Suite | 10 Mins to Mountains | A/C
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Enjoy a comfortable stay in this cozy living space with a fully equipped kitchen, dining area, and comfortable seating.

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

8.8 out of 10, Excellent, (5)
"Comfortable stay. Great location. Pool n spa was very nice and new."
The price is CA $196
CA $475 total
includes taxes & fees
Jul 14 - Jul 15
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Enjoy al fresco dining on the patio, surrounded by a forest with a barbecue grill and comfortable seating for four.

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

9.0 out of 10, Wonderful, (18)
"Great price, location, and property owner. "
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Modern Ski Château - 4 min from Killington Ski mountain lifts
Enjoy cooking in this well-lit kitchen with a central island, oven, and 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 $1,851
CA $2,705 total
includes taxes & fees
Jul 15 - Jul 16
Modern Ski Château - 4 min from Killington Ski mountain lifts
Riverfront studio with river view, full kitchen, & free WiFi
Compact kitchen with a stove, microwave, refrigerator, and dishwasher, featuring a sink with a window above.

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 CA $75
CA $316 total
includes taxes & fees
Jul 14 - Jul 15
Riverfront studio with river view, full kitchen, & free WiFi
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Stroll through a charming small town surrounded by majestic mountains.

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

9.8 out of 10, Exceptional, (170)
"Great location, perfect size, awesome to be able to bring the pooch. Will look to book again next season."
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Vermont Retreat
Efficient kitchen with a double sink, refrigerator, stove, and toaster.

Vermont Retreat

10.0 out of 10, Exceptional, (21)
"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
Efficient condo near slopes with kitchenette & great location
Enjoy the serene view from this deck, offering a glimpse of the snow-covered landscape and the building beyond.

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 $73
CA $234 total
includes taxes & fees
Jul 20 - Jul 21
Efficient condo near slopes with kitchenette & great location
Views! Sauna Historic | Woodstock Riverside Escape
Relax on the porch amidst lush greenery and trees, surrounded by a serene natural setting.

Views! Sauna Historic | Woodstock Riverside Escape

10.0 out of 10, Exceptional, (1)
"The home was well-appointed and very comfortable. Love the location! The property managers were extremely responsive, as well. Highly recommend this home."
Views! Sauna Historic | Woodstock Riverside Escape
Studio 154 tucked away, peaceful and convenient access to the upper valley NH.
Cozy apartment with a sloped ceiling, flat-screen TV, and a comfortable bed.

Studio 154 tucked away, peaceful and convenient access to the upper valley NH.

10.0 out of 10, Exceptional, (20)
"Really great setup and made for great ski weekend. Really well stocked, clean and felt like home. Thanks for awesome stay!"
Studio 154 tucked away, peaceful and convenient access to the upper valley NH.
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.
Skate and show off your skills at this skatepark with a wooden ramp and flat area.

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 $226
CA $325 total
includes taxes & fees
Jul 15 - Jul 16
Cozy studio with WiFi and fitness room in Springfield. Close to Okemo and Magic.
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
Escape to a secluded mountain retreat with a cabin nestled among towering conifers.

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

9.6 out of 10, Exceptional, (15)
"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.
Bright Condo w/ Community Perks: Near Ski Quechee!
Apartment (2 Bedrooms) | Interior

Bright Condo w/ Community Perks: Near Ski Quechee!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place for 2 couples to relax and enjoy the fall sights.Only problem was the master bedroom bath. The bathtub drain was blocked and took 30 minutes to drain the water. Property owner was unable to get a plumber over the weekend, so I removed the stopper cleaned a lot of hair and waste, replaced the stopper and bathtub drained real good after that. "
Bright Condo w/ Community Perks: Near Ski Quechee!
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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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. Onsite laundry facilities and a hot tub are on site. Hawks Mountain Farm, full apartment on a working farm.: 12.7 mi/20.4 km away in Chester. Free WiFi, private patios, and sofa beds are included. Nana's House: It's located in Bridgewater, 14.2 mi/22.9 km from Windsor. Includes free WiFi and Smart TVs.
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.