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

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Our top choices for Windsor apartments

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
28 Jun - 29 Jun
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

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 996 total
includes taxes & fees
29 Jun - 30 Jun
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

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 AED 366
AED 852 total
includes taxes & fees
28 Jun - 29 Jun
Efficient condo near slopes with kitchenette & great location

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 AED 366
AED 877 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Studio Condo with Great Location, WiFi & Kitchenette

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
28 Jun - 29 Jun
Spacious mountain studio with free WiFi & full kitchen - close to skiing

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 443
AED 1,214 total
includes taxes & fees
28 Jun - 29 Jun
BearNecessities- Pool, Hot Tub, Gym

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 AED 619
AED 781 total
includes taxes & fees
5 Jul - 6 Jul
Okemo | Spacious Executive Room w Amenities Nearby

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
28 Jun - 29 Jun
Little Bear Landing- Pool, Bike 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.
The price is AED 778
AED 1,603 total
includes taxes & fees
1 Jul - 2 Jul
BearsLair- Pool, Hot tub, Bike to Mountain!

Apres Hideaway- Bike to Mountain, Pool, Hiking!

Apres Hideaway- Bike to Mountain, Pool, Hiking!
Killington
The price is AED 774
AED 1,599 total
includes taxes & fees
28 Jun - 29 Jun
Apres Hideaway- Bike to Mountain, Pool, Hiking!

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

Rabbit Hole | AC, Pool, Hot Tub, Near Resort

Rabbit Hole | 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 AED 1,102
AED 2,351 total
includes taxes & fees
30 Jun - 1 Jul
Rabbit Hole | AC, Pool, Hot Tub, Near 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 995
AED 2,197 total
includes taxes & fees
29 Jun - 30 Jun
Robin`s Nest- Pool, Gym, Fireplace, Near the AT

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 1,613 total
includes taxes & fees
29 Jun - 30 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.
The price is AED 793
AED 1,621 total
includes taxes & fees
1 Jul - 2 Jul
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort

Charming 2BR Hanover Apartment—Walk to Dartmouth

Charming 2BR Hanover Apartment—Walk to Dartmouth
Hanover
The price is AED 1,719
AED 2,973 total
includes taxes & fees
11 Jul - 12 Jul
Charming 2BR Hanover Apartment—Walk to Dartmouth

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
5 Jul - 6 Jul
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

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

BaseLoj - Pool, Firepit, Bike to Mountain!

BaseLoj - Pool, Firepit, Bike to Mountain!
Killington
10.0 out of 10, Exceptional, (5 reviews)
"Great location, everything we needed for our vacation was there, and really easy access to the multiple base lodges. Skiing conditions were excellent. "
United States
Scott R.
The price is AED 983
AED 2,196 total
includes taxes & fees
30 Jun - 1 Jul
BaseLoj - Pool, Firepit, Bike to Mountain!

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 AED 366
AED 1,134 total
includes taxes & fees
28 Jun - 29 Jun
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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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