A snow-covered river valley with a bridge and a town.

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor apartments

A large house with a fire pit and outdoor seating.

1. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is CA $151
CA $285 total
includes taxes & fees
Nov 5 - Nov 6
Bridgewater Living - Ben&Jerry Suite
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

2. Modern Village Condo Steps to Dining & Ski Shuttle

Modern Village Condo Steps to Dining & Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is CA $117
CA $356 total
includes taxes & fees
Nov 5 - Nov 6
Modern Village Condo Steps to Dining & Ski Shuttle
A large house with a fire pit and outdoor seating.

3. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $151
CA $282 total
includes taxes & fees
Nov 5 - Nov 6
Bridgewater Living - Ski VT Suite
A large house with a fire pit and outdoor seating.

4. Bridgewater Living - Long Trail Suite

Bridgewater Living - Long Trail Suite
Bridgewater
8.0 out of 10, Very good, (1 review)
"The studio was clean with rustic feel. On the main road so easy to find. Short drive to restaurant and brewery. About 1/2 to Woodstock."
United States
Ann
The price is CA $151
CA $283 total
includes taxes & fees
Nov 9 - Nov 10
Bridgewater Living - Long Trail Suite
A golf course with a winding path, trees, and a hilly landscape.

5. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $157
CA $438 total
includes taxes & fees
Nov 7 - Nov 8
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A residential area with houses, a swimming pool, and a mountain backdrop.

6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
United States
Nathan H.
The price is CA $108
CA $339 total
includes taxes & fees
Nov 5 - Nov 6
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A large house with a fire pit and outdoor seating.

7. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is CA $151
CA $283 total
includes taxes & fees
Nov 8 - Nov 9
Bridgewater Living - Woodstock Suite
A golf course with a winding path, trees, and a distant mountain range.

8. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $157
CA $332 total
includes taxes & fees
Nov 7 - Nov 8
Compact downtown studio condo with kitchenette near the Okemo slopes
A bedroom with two beds, a dresser, a desk, and a window with a view of trees.

9. Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131

Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131
Killington
The price is CA $110
CA $346 total
includes taxes & fees
Nov 5 - Nov 6
Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131
This aerial shows where the outdoor pool sits among the buildings. Pool use follows the seasonal operating schedule.

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

Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Killington
7.4 out of 10, Good, (3 reviews)
"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 "
United States
Joe S.
The price is CA $118
CA $357 total
includes taxes & fees
Nov 5 - Nov 6
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
A storefront with a sign that reads 'Southern Pub Cafe' and a Christmas tree outside.

11. Modern 3BR/2BA | 3 Min to Okemo Mountain

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is CA $287
CA $861 total
includes taxes & fees
Nov 5 - Nov 6
Modern 3BR/2BA | 3 Min to Okemo Mountain
A multi-story building with a clock on the facade, balconies, and a small garden area.

12. Mountain Green Resort studio in the main building with indoor pool access

Mountain Green Resort studio in the main building with indoor pool access
Killington
The price is CA $132
CA $409 total
includes taxes & fees
Nov 6 - Nov 7
Mountain Green Resort studio in the main building with indoor pool access
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

13. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is CA $348
CA $416 total
includes taxes & fees
Nov 9 - Nov 10
Okemo | Studio Condo + Close to All Amenities
A small cabin with a fire pit and outdoor seating.

14. Mountain Green upper-floor condo with golf course views from the balcony

Mountain Green upper-floor condo with golf course views from the balcony
Killington
The price is CA $165
CA $436 total
includes taxes & fees
Nov 29 - Nov 30
Mountain Green upper-floor condo with golf course views from the balcony
A golf course with multiple greens, a clubhouse, and a parking area.

15. BearNecessities- Pool, Hot Tub, Gym

BearNecessities- Pool, Hot Tub, Gym
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The unit was right across from Killington with many great amenities. The place was very cozy and perfect for a quick stay before a day of skiing."
United States
Matthew S.
The price is CA $178
CA $448 total
includes taxes & fees
Nov 5 - Nov 6
BearNecessities- Pool, Hot Tub, Gym
A two-story house with a covered porch and a snow-covered landscape.

16. 11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Cute place right in town, super convenient to the mountain (although if you’re relying on the shuttle it’s only once an hour so can be annoying if you don’t time it well). Rooms comfortably slept 4 plus one on the sofa bed, annd everything was in good shape, Andrew and Jillian were great hosts!"
United States
Max R.
The price is CA $377
CA $832 total
includes taxes & fees
Nov 5 - Nov 6
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining
A wooden gazebo with a roof, surrounded by lush greenery and flowers.

17. Wade`s World Ski Home Shuttle location

Wade`s World Ski Home Shuttle location
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Gorgeous little spot. Slept for comfortably had a fantastic vacation weekend. Great snow first class owners. Perfect for a ski weekend."
United States
Michael K.
The price is CA $328
CA $611 total
includes taxes & fees
Nov 5 - Nov 6
Wade`s World Ski Home Shuttle location
A dining area with a wooden table, chairs, a vase with flowers, a fireplace, and a view of trees through large windows.

18. Trails Together! Pool, Hot tub, Sauna, Near Resort

Trails Together! Pool, Hot tub, Sauna, Near Resort
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was great. The condo was spacious with plenty of storage space. Everything we needed was there. The hosts were quickly responsive to questions. The welcome treats were such a nice touch."
United States
Stephanie D.
The price is CA $363
CA $657 total
includes taxes & fees
Nov 9 - Nov 10
Trails Together! Pool, Hot tub, Sauna, Near Resort
Interior

19. Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
2.0 star property
Killington
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

20. Jack S`Bearo - Slopes, Fireplace, Pool

Jack S`Bearo - Slopes, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is CA $187
CA $375 total
includes taxes & fees
Nov 5 - Nov 6
Jack S`Bearo - Slopes, Fireplace, Pool
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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Top Windsor Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Cosy and lovely. Couldnt have been nicer. The breakfast muffins were homemade and the bestbive ever had"
chiara 1-night trip
Posted 5 hours ago
On The River Inn

Find out more about Windsor

Windsor Apartments information

Number of reviews
54
Accommodation
165 Apartments
Lowest Price
CA $282
Highest Price
CA $861

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: Charming King Loft in Downtown Woodstock: Located in Woodstock, 12 mi/19.3 km from the heart of Windsor. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located 16.5 mi/26.6 km away in Ludlow. Free WiFi, private patios, and fireplaces are included. A fitness center and onsite laundry facilities are on site. Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK: Located 16.5 mi/26.6 km away in Ludlow. Laundry facilities, free WiFi, and private patios are included. A fitness center and onsite laundry facilities are on site. Hawks Mountain Farm, full upstairs apartment on a working farm.: It's located in Chester, 12.7 mi/20.4 km from Windsor. Includes free WiFi, private patios, and 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.

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