Cornish-Windsor Covered Bridge

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Our top choices for Windsor apartments

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, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is AED 463
AED 1,000 total
includes taxes & fees
22 Jun - 23 Jun
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
Clean & bright condo with mountain views & modern kitchen - walk to lifts

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.
BearNecessities- Pool, Hot Tub, Gym

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is AED 382
AED 578 total
includes taxes & fees
22 Jun - 23 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

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
The price is AED 366
AED 1,134 total
includes taxes & fees
22 Jun - 23 Jun
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
The price is AED 366
AED 852 total
includes taxes & fees
22 Jun - 23 Jun
Efficient condo near slopes with kitchenette & great location

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is AED 769
AED 983 total
includes taxes & fees
28 Jun - 29 Jun
Okemo | Studio Condo + Loft | Near Slopes + Pool

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 AED 343
AED 1,125 total
includes taxes & fees
22 Jun - 23 Jun
Spacious mountain studio with free WiFi & full kitchen - close to skiing

Little Bear Landing- Pool, Bike to resort!

Little Bear Landing- Pool, Bike to resort!
Killington
The price is AED 778
AED 1,603 total
includes taxes & fees
22 Jun - 23 Jun
Little Bear Landing- Pool, Bike to resort!

Robin`s Nest- Pool, Gym, Fireplace, Near the AT

Robin`s Nest- Pool, Gym, Fireplace, Near the AT
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Great location to Pico Mountain, clean, warm and spacious! "
United States
Leslie D.
The price is AED 1,039
AED 2,267 total
includes taxes & fees
29 Jun - 30 Jun
Robin`s Nest- Pool, Gym, Fireplace, Near the AT

Pinnacle C16

Pinnacle C16
3.0 star property
Killington
8.8 out of 10, Excellent, (3 reviews)
"Ski trip - warm, cozy, quiet, 2 min ride on free shuttle bus to base."
United States
Steve
The price is AED 569
AED 1,634 total
includes taxes & fees
26 Jun - 27 Jun
Pinnacle C16

Rabbit Hole | Bike Park, Hot Tub, Pool, AC

Rabbit Hole | Bike Park, Hot Tub, Pool, AC
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 AED 1,158
AED 2,406 total
includes taxes & fees
1 Jul - 2 Jul
Rabbit Hole | Bike Park, Hot Tub, Pool, AC

BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is AED 1,055
AED 2,289 total
includes taxes & fees
22 Jun - 23 Jun
BlueBird Escape- Pool, Near Bike Park and Golf!

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 AED 778
AED 1,603 total
includes taxes & fees
28 Jun - 29 Jun
Wade`s World- AC, Pool, Tennis, Bike to Mountain

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

Trails Together! Pool, Hot tub, Sauna, Near Resort
Killington
10.0 out of 10, Exceptional, (1 review)
"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 AED 793
AED 1,621 total
includes taxes & fees
22 Jun - 23 Jun
Trails Together! Pool, Hot tub, Sauna, Near Resort

Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort

Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Everything we needed. "
United States
patrick w.
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort

BearsLair- Pool, Hot tub, Bike to Mountain!

BearsLair- Pool, Hot tub, Bike to Mountain!
Killington
10.0 out of 10, Exceptional, (1 review)
"The Host is amazing, they responded quickly to any questions or concerns we had then to our surprise they left us some gifts from Vermont to enjoy during our stay. The unit was immaculate and is extremely easy and close to get to the slopes and when we were done skiing the hot tub and pool were a great way to reflect on the day. The condo complex has a pro shop for rental equipment as well as a bar/restaurant on site. This place is 5 star "
United States
Steve D.
BearsLair- Pool, Hot tub, Bike to Mountain!

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
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 1,245
AED 2,820 total
includes taxes & fees
28 Jun - 29 Jun
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

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 AED 382
AED 578 total
includes taxes & fees
24 Jun - 25 Jun
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Pinnacle F21 Condo | Pool, Hot Tub | Golf Nearby

Pinnacle F21 Condo | Pool, Hot Tub | Golf Nearby
Killington
9.4 out of 10, Exceptional, (6 reviews)
"Very convenient and the facilities (hot tub and sauna) are very good. The shuttle bus is extremely helpful. Will stay here again."
United States
Jeanine
The price is AED 702
AED 2,376 total
includes taxes & fees
26 Jun - 27 Jun
Pinnacle F21 Condo | Pool, Hot Tub | Golf Nearby
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?
Below you'll find a favorite apartment in the area to consider: 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.
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 Brownsville Trail 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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