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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor apartments

Exterior

1. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is CA $166
CA $314 total
includes taxes & fees
Sep 6 - Sep 7
Bridgewater Living - Ski VT Suite
Golf

2. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $138
CA $317 total
includes taxes & fees
Sep 8 - Sep 9
Efficient condo near slopes with kitchenette & great location
Exterior

3. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is CA $138
CA $326 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Exterior

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

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is CA $248
CA $427 total
includes taxes & fees
Sep 6 - Sep 7
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Exterior

5. Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is CA $155
CA $231 total
includes taxes & fees
Sep 6 - Sep 7
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Property grounds

6. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is CA $166
CA $315 total
includes taxes & fees
Sep 6 - Sep 7
Bridgewater Living - Ben&Jerry Suite
Property grounds

7. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is CA $166
CA $314 total
includes taxes & fees
Sep 6 - Sep 7
Bridgewater Living - Woodstock Suite
Interior

8. Bridgewater Living - Long Trail Suite

Bridgewater Living - Long Trail Suite
Bridgewater
The price is CA $166
CA $314 total
includes taxes & fees
Sep 6 - Sep 7
Bridgewater Living - Long Trail Suite
Exterior

9. 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, (4 reviews)
"Place was great"
United States
Nathan H.
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Outdoor dining

10. Okemo | Spacious Executive Room w Amenities Nearby

Okemo | Spacious Executive Room w Amenities Nearby
Jackson Gore Base Area
9.0 out of 10, Wonderful, (2 reviews)
"We waited outside the room for 30 minutes to check in at exactly 5 PM when it was obvious that the room was ready earlier. The lack of early check in was a hassle."
United States
David K.
The price is CA $299
CA $378 total
includes taxes & fees
Sep 7 - Sep 8
Okemo | Spacious Executive Room w Amenities Nearby
1 bedroom, desk, iron/ironing board, WiFi (free)

11. 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 $94
CA $335 total
includes taxes & fees
Sep 8 - Sep 9
Charming Killington Studio w/ Pool. Bus Route. Ski Rental Deals! - Killington Center Suites 131
Exterior

12. 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.
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.
Golf

13. 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 $166
CA $451 total
includes taxes & fees
Sep 8 - Sep 9
BearNecessities- Pool, Hot Tub, Gym
Living area

14. 2-BD short drive to DHMC & Dartmouth College

2-BD short drive to DHMC & Dartmouth College
Sharon
The price is CA $262
CA $425 total
includes taxes & fees
Sep 7 - Sep 8
2-BD short drive to DHMC & Dartmouth College
1 bedroom, desk, iron/ironing board, travel crib

15. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (16 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is CA $174
CA $376 total
includes taxes & fees
Sep 7 - Sep 8
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Golf

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

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is CA $138
CA $426 total
includes taxes & fees
Sep 7 - Sep 8
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Exterior

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

Spacious mountain studio with free WiFi & full kitchen - close to skiing
Killington
The price is CA $116
CA $400 total
includes taxes & fees
Sep 8 - Sep 9
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Terrace/patio

18. Wade`s World- AC, Pool, Tennis, Bike to Mountain

Wade`s World- AC, Pool, Tennis, Bike to Mountain
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 $314
CA $624 total
includes taxes & fees
Sep 6 - Sep 7
Wade`s World- AC, Pool, Tennis, Bike to Mountain
Pool

19. RabbitHole | AC, Pool, Hot Tub, Near Resort

RabbitHole | AC, Pool, Hot Tub, Near Resort
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Our hosts were super communicative. The check in process was smooth. The condo was clean and well appointed. Beds good. Our hosts even gave us some local coffee and maple syrup as a welcome gift (along with a few other things). Definitely recommend "
United States
Amy G.
The price is CA $433
CA $855 total
includes taxes & fees
Sep 6 - Sep 7
RabbitHole | AC, Pool, Hot Tub, Near Resort
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

The Jackson

The Jackson

10/10 Excellent
"We had a lovely 1 night stay at the quaint Jackson. We enjoyed the wine & cheese hour, had dinner at Oakes & Evelyn (on site but not part of the hotel) and enjoyed a nightcap on the porch. The bed was super comfortable, sheets were clean and crisp, robes were Frette and products smelled great. The property is gorgeous and Woodstock as a town is a delight."
Karl 1-night trip
Posted 1 hour ago
The Jackson

Find out more about Windsor

Windsor Apartments information

Number of reviews
131
Accommodation
152 Apartments
Lowest Price
CA $231
Highest Price
CA $855

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: Hawks Mountain Farm, full apartment on a working farm.: Situated in Chester, 12.7 mi/20.4 km from the heart of Windsor. Includes free WiFi, private patios, and sofa beds. Charming King Loft in Downtown Woodstock: Located 12 mi/19.3 km away in Woodstock. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.: Located in Ludlow, 16.5 mi/26.6 km from Windsor. Includes free WiFi, private patios, and fireplaces. A fitness center and onsite laundry facilities 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, Mt Ascutney State Park and Harpoon Brewery 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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