Search Apartments in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Windsor apartments

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 466
AED 928 total
includes taxes & fees
10 Feb - 11 Feb
Vermont Suite | 10 Min to Woodstock & Killington
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
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is AED 253
AED 917 total
includes taxes & fees
10 Feb - 11 Feb
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Golf

LilBear- Shuttle, FIreplace, Pool, Hot Tub.

LilBear- Shuttle, FIreplace, Pool, Hot Tub.
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location and comfortable condo."
United States
Timothy R.
The price is AED 444
AED 1,241 total
includes taxes & fees
9 Mar - 10 Mar
LilBear- Shuttle, FIreplace, Pool, Hot Tub.
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is AED 474
AED 957 total
includes taxes & fees
10 Feb - 11 Feb
Efficient condo near slopes with kitchenette & great location
Fridge, microwave, oven, stovetop

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is AED 1,781
AED 2,830 total
includes taxes & fees
16 Feb - 17 Feb
Jack S`Bearo - Slopes, Fireplace, 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
8.6 out of 10, Excellent, (12 reviews)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is AED 481
AED 1,275 total
includes taxes & fees
10 Feb - 11 Feb
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Exterior

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Ludlow
9.8 out of 10, Exceptional, (173 reviews)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
United States
Aidan O.
The price is AED 735
AED 1,253 total
includes taxes & fees
8 Feb - 9 Feb
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Smart TV, fireplace

CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"It was a very comfortable place for my family and pups! We really enjoyed it."
United States
Su C.
The price is AED 823
AED 1,869 total
includes taxes & fees
9 Feb - 10 Feb
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
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, (20 reviews)
"Communication was excellent and service was great."
United States
Emmanuella A.
The price is AED 503
AED 1,320 total
includes taxes & fees
9 Feb - 10 Feb
Spacious mountain studio with free WiFi & full kitchen - close to skiing
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 419
AED 868 total
includes taxes & fees
9 Feb - 10 Feb
Vermont Double Queen Suite | 10 Mins to Killington
Exterior

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is AED 1,313
AED 1,838 total
includes taxes & fees
21 Feb - 22 Feb
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Interior

MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort

MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort
Killington
10.0 out of 10, Exceptional, (4 reviews)
"The condo was perfect! "
United States
Mandy b.
The price is AED 1,242
AED 2,654 total
includes taxes & fees
10 Feb - 11 Feb
MightyMoose- Pool, Hot tub, Sauna, Gym, Near Resort
Exterior

Scandibearia- Sauna, Shuttle, Pool , Hot tub

Scandibearia- Sauna, Shuttle, Pool , Hot tub
Killington
The price is AED 1,016
AED 1,753 total
includes taxes & fees
26 Feb - 27 Feb
Scandibearia- Sauna, Shuttle, Pool , Hot tub
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 360
AED 795 total
includes taxes & fees
10 Mar - 11 Mar
Vermont Suite | 10 Min to Killington & Woodstock
Golf

BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off

BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Loved it, clean, feels like home will come again!"
United States
Theresa R.
The price is AED 1,092
AED 2,530 total
includes taxes & fees
10 Feb - 11 Feb
BaseLoj - Hot tub, Pool, Sauna, Shuttle On/Off
Terrace/patio

Downtown Remodel: Restaurants & Mountain Shuttle

Downtown Remodel: Restaurants & Mountain Shuttle
Ludlow
The price is AED 1,190
AED 2,401 total
includes taxes & fees
9 Feb - 10 Feb
Downtown Remodel: Restaurants & Mountain Shuttle
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.
The price is AED 722
AED 1,575 total
includes taxes & fees
12 Feb - 13 Feb
BearNecessities- Pool, Hot Tub, Gym
Smart TV, fireplace

Robins Nest- FirePlace, Near Pico, Pool.

Robins Nest- FirePlace, Near Pico, Pool.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Great location to Pico Mountain, clean, warm and spacious! "
United States
Leslie D.
The price is AED 1,151
AED 2,606 total
includes taxes & fees
10 Feb - 11 Feb
Robins Nest- FirePlace, Near Pico, Pool.
Golf

MooseTracks- Hot Tub, Pool, Gym, Sauna, Shuttle!

MooseTracks- Hot Tub, Pool, Gym, Sauna, Shuttle!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Easy access to skiing. Clean and comfortable accommodations. Gym/Hot tub is in a separate building, but still close."
United States
Anonymous traveler
The price is AED 1,151
AED 2,606 total
includes taxes & fees
10 Feb - 11 Feb
MooseTracks- Hot Tub, Pool, Gym, Sauna, Shuttle!
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Great room, lovely view and a wonderful town "
Derek 1-night trip
Posted 3 days ago
The Shire Woodstock

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 hotels and other accommodations. Though there aren't many apartments, we can help you search for 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 such as a kitchen. You can also filter by similar properties such as vacation homes, condos, or cabins. Make time to visit the region's favorite places like Okemo Mountain Resort.
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: Mountain Green Resort: Located 22.9 mi/36.9 km away in Killington. Laundry facilities, free WiFi, and separate dining areas are included. Free parking and an outdoor pool 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, 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.

Explore a world of travel with Expedia