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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Windsor apartments

Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is AED 309
AED 731 total
includes taxes & fees
11 May - 12 May
Vermont Double Queen Suite | 10 Mins to Killington
Fridge, microwave, oven, stovetop

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, (14 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Golf

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)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is AED 349
AED 783 total
includes taxes & fees
8 May - 9 May
Efficient condo near slopes with kitchenette & great location
Golf

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
Indoor pool

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

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.0 out of 10, Good, (48 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Interior

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
10 May - 11 May
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Golf

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 349
AED 1,083 total
includes taxes & fees
12 May - 13 May
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Outdoor dining

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 714
AED 909 total
includes taxes & fees
10 May - 11 May
Okemo | Studio Condo + Loft | Near Slopes + Pool
Golf

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)
"Overall, property was excellent. Only issue was no ac. A fan was provided but air was not moving in the little apartment. It was also unusually hot when were there. Location was excellent for all the hiking we had planned :-)"
United States
Kim C.
Bearitime Lodge Pool, Gym, Hot Tub, Close to Resort
Terrace/patio

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
8 May - 9 May
Little Bear Landing- Pool, Bike to resort!
Indoor pool

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

Spacious mountain studio with free WiFi & full kitchen - close to skiing
Killington
6.4 out of 10, (21 reviews)
"Communication was excellent and the condo was extremely clean."
United States
Susan L.
The price is AED 364
AED 1,127 total
includes taxes & fees
8 May - 9 May
Spacious mountain studio with free WiFi & full kitchen - close to skiing
Interior

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

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 1,091
AED 2,334 total
includes taxes & fees
8 May - 9 May
Rabbit Hole | Bike Park, Hot Tub, Pool, AC
Golf

LilBear- AC, Pool, Sauna, Hot Tub, Near Resort

LilBear- AC, Pool, Sauna, Hot Tub, Near Resort
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great location and comfortable condo."
United States
Timothy R.
LilBear- AC, Pool, Sauna, Hot Tub, Near Resort
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is AED 290
AED 707 total
includes taxes & fees
17 May - 18 May
Vermont Suite | 10 Min to Killington & Woodstock
Living area

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM

Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Killington
7.8 out of 10, Good, (6 reviews)
"Comfortable stay. Great location. Pool n spa was very nice and new."
United States
Jerry G.
The price is AED 584
AED 1,349 total
includes taxes & fees
31 May - 1 Jun
Killington 1 Bed 1 Bath Condo 5 Min walk to Mountain Indoor Pool, Hot Tub ,GYM
Property grounds

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is AED 294
AED 715 total
includes taxes & fees
11 May - 12 May
Vermont Suite | 10 Min to Woodstock & Killington
Property grounds

Vermont Suite | Minutes to Killington | Skiing

Vermont Suite | Minutes to Killington | Skiing
Bridgewater
8.0 out of 10, Very Good, (2 reviews)
"clean, easy to check in and out, convenient location to the GMHA grounds - we stay here every summer! "
United States
Amanda K.
The price is AED 272
AED 687 total
includes taxes & fees
10 May - 11 May
Vermont Suite | Minutes to Killington | Skiing
Golf

Moose Tracks Lodge - Pool, Hot Tub, Golf, Sauna

Moose Tracks Lodge - Pool, Hot Tub, Golf, Sauna
Killington
10.0 out of 10, Exceptional, (9 reviews)
"Great condo! Less than 5 min drive (and walking distance) from the resort. Well maintained and has all amenities to make the stay enjoyable. "
United States
Stephanie H.
Moose Tracks Lodge - Pool, Hot Tub, Golf, Sauna
Smart TV, fireplace

BearHug AC, Pool, Hot Tub, Tennis, Close to Resort

BearHug AC, Pool, Hot Tub, Tennis, Close to Resort
Killington
10.0 out of 10, Exceptional, (10 reviews)
"Great experience staying at Bear Hug for a New Year’s ski trip. Hosts Dan and Holly were very responsive and the unit was as advertised. Made great use of he fireplace and close access to slopes. "
United States
Matthew M.
The price is AED 1,347
AED 2,907 total
includes taxes & fees
8 May - 9 May
BearHug AC, Pool, Hot Tub, Tennis, Close to 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

Best Western West Lebanon-Hanover Hotel

Best Western West Lebanon-Hanover Hotel

10/10 Excellent
"Very nice place and value for the money too"
Mohamed 2-night trip
Posted 2 hours ago
Best Western West Lebanon-Hanover Hotel

Frequently asked questions

What's it like to stay at an apartment in Windsor?
There are plenty of places to stay in Windsor with 22 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 are some of the favorite apartments in the area: 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. 3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view: Located in Cavendish, 14.1 mi/22.8 km away. Includes free WiFi, separate dining areas, and jetted bathtubs. Access to onsite laundry facilities is available on site. Hawks Mountain Farm, full apartment on a working farm.: 12.7 mi/20.4 km away in Chester. Free WiFi, private patios, and sofa beds are included.
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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