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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Condo Rentals in Windsor

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (54)
"Cozy but all the amenities, great location"
$151 nightly
The price is $170
Sep 29 - Sep 30
Total with taxes and fees
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Beautiful Spacious Condo at Killington Resort
Fridge, microwave, oven, stovetop

Beautiful Spacious Condo at Killington Resort

9.8 out of 10, Exceptional, (39)
"Very cozy and comfortable. We loved tge fire place!"
Beautiful Spacious Condo at Killington Resort
Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.
Fridge, microwave, oven, stovetop

Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.

10.0 out of 10, Exceptional, (23)
"Awesome place to stay. "
Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.
Killington Sapphire
Living area

Killington Sapphire

9.2 out of 10, Wonderful, (7)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
Trail Creek 75 | Condo in Killington
Interior

Trail Creek 75 | Condo in Killington

9.8 out of 10, Exceptional, (16)
"Very affodrable charming 2 bedroom that accomodated our family perfectly. We enjoyed the use of the indoor pool, hot tub and game room. We will be be back!"
Trail Creek 75 | Condo in Killington
Fireplace, Game Room, Corner Condo - Sugar Hill 3E
Fridge, microwave, oven, stovetop

Fireplace, Game Room, Corner Condo - Sugar Hill 3E

6.0 out of 10, (1)
Fireplace, Game Room, Corner Condo - Sugar Hill 3E
Large One Bedroom Mountain Side
Fridge, microwave, oven, stovetop

Large One Bedroom Mountain Side

9.2 out of 10, Wonderful, (10)
"We had a great time staying here. We could not be happier with the location in relation to the closeness to the slopes. The pool and sauna were a great bonus! We would def stay here again."
Large One Bedroom Mountain Side
Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!
Indoor pool, a heated pool

Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!

10.0 out of 10, Exceptional, (57)
"We had a great time at this condo! It was very comfortable and clean. Would stay there again."
Luxe Trailside! Bike + Ski On/Off. Closest unit to hot tub, lift, hotel & trail!
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Property grounds

Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer

9.4 out of 10, Exceptional, (27)
"Great ski in ski out location. Lift is right next to condo"
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Killington Retreat
Exterior

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (11)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

10.0 out of 10, Exceptional, (97)
"Wonderful two bedroom condo, fantastic communication from the manager, easy everything, parking, accessing the beautiful unit, checking out, just perfect!"
$282 nightly
The price is $306
Sep 28 - Sep 29
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Walk-to-lifts, ski-in trail condo, sauna, indoor pool, hot tub, gym, w/d
Interior

Walk-to-lifts, ski-in trail condo, sauna, indoor pool, hot tub, gym, w/d

9.0 out of 10, Wonderful, (24)
"Awesome accommodations "
Walk-to-lifts, ski-in trail condo, sauna, indoor pool, hot tub, gym, w/d
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
Indoor pool, a heated pool

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

10.0 out of 10, Exceptional, (20)
"great spot for kids. easy check in and lots of local spots! definitely download guide! "
$367 nightly
The price is $415
Oct 7 - Oct 8
Total with taxes and fees
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.
Fridge, microwave, oven, stovetop

The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.

8.8 out of 10, Excellent, (3)
"Perfect spot for a Killington ski weekend. Just two of us, and that was ideal. So close to the mountain, and so well maintained. I highly recommend this rental for our next trip up."
The Summit Suite at Whiffletree Killington: Shuttle Bus. Pool. Discounted Ski Rentals.
NEW Killington Studio: Great Location! Comfy. 431
Exterior

NEW Killington Studio: Great Location! Comfy. 431

9.6 out of 10, Exceptional, (4)
"Great place to stay!"
NEW Killington Studio: Great Location! Comfy. 431
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Property grounds

Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer

9.2 out of 10, Wonderful, (51)
"The location & tranquility !"
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Okemo Condo on Bus Route in Center of Town
Fridge, microwave, oven, stovetop

Okemo Condo on Bus Route in Center of Town

9.8 out of 10, Exceptional, (7)
"Great location, perfect for family trips. Recently updated amenities. Would recommend. "
Okemo Condo on Bus Route in Center of Town
1 BR Best Location! Pools/Massage Chair/Hottubs! Summer '25 long term rental ok!
Fridge, microwave, oven, stovetop

1 BR Best Location! Pools/Massage Chair/Hottubs! Summer '25 long term rental ok!

10.0 out of 10, Exceptional, (13)
"My family had a wonderful ski trip staying at this condo! "
1 BR Best Location! Pools/Massage Chair/Hottubs! Summer '25 long term rental ok!
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.4 out of 10, Exceptional, (15)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
$220 nightly
The price is $248
Sep 29 - Sep 30
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 2 days ago
The Mountain Inn at Killington

Find out more about Windsor

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
376
Accommodation
922 Condo Rentals
Lowest Price
$170
Highest Price
$415

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