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

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Our top choices for Windsor apartments

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 AED 397
AED 757 total
includes taxes & fees
4 Nov - 5 Nov
Bridgewater Living - Ben&Jerry Suite

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 AED 386
AED 992 total
includes taxes & fees
17 Nov - 18 Nov
Modern Village Condo Steps to Dining & Ski Shuttle

3. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is AED 397
AED 753 total
includes taxes & fees
4 Nov - 5 Nov
Bridgewater Living - Ski VT Suite

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 AED 397
AED 753 total
includes taxes & fees
4 Nov - 5 Nov
Bridgewater Living - Long Trail Suite

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 AED 412
AED 1,109 total
includes taxes & fees
17 Nov - 18 Nov
First-floor downtown studio near dining and gear shops, under a mile to Okemo

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 AED 283
AED 904 total
includes taxes & fees
4 Nov - 5 Nov
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

7. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is AED 397
AED 753 total
includes taxes & fees
4 Nov - 5 Nov
Bridgewater Living - Woodstock Suite

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 AED 412
AED 848 total
includes taxes & fees
17 Nov - 18 Nov
Compact downtown studio condo with kitchenette near the Okemo slopes

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

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 AED 310
AED 937 total
includes taxes & fees
4 Nov - 5 Nov
Skiers Suite Annex: Renovated Studio on the Bus Route. Discounted Ski Rentals.

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

Modern 3BR/2BA | 3 Min to Okemo Mountain
Ludlow
The price is AED 754
AED 2,159 total
includes taxes & fees
17 Nov - 18 Nov
Modern 3BR/2BA | 3 Min to Okemo Mountain

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 AED 347
AED 1,076 total
includes taxes & fees
17 Nov - 18 Nov
Mountain Green Resort studio in the main building with indoor pool access

13. Okemo | Studio Condo + Close to All Amenities

Okemo | Studio Condo + Close to All Amenities
Jackson Gore Base Area
The price is AED 915
AED 1,043 total
includes taxes & fees
17 Nov - 18 Nov
Okemo | Studio Condo + Close to All Amenities

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 AED 433
AED 1,149 total
includes taxes & fees
29 Nov - 30 Nov
Mountain Green upper-floor condo with golf course views from the balcony

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 AED 469
AED 1,185 total
includes taxes & fees
4 Nov - 5 Nov
BearNecessities- Pool, Hot Tub, Gym

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 AED 991
AED 2,185 total
includes taxes & fees
4 Nov - 5 Nov
11 Gables Treehouse- Shuttle Bus, Short Walk to Shops, Bars, Dining

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 AED 862
AED 1,617 total
includes taxes & fees
4 Nov - 5 Nov
Wade`s World Ski Home Shuttle location

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

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

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 AED 490
AED 986 total
includes taxes & fees
4 Nov - 5 Nov
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

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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