Photo by William E Berry Jr.

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Compare 690 Condo Rentals in Windsor with updated reviews, rates, and availability.

All-season resort getaway with pool, tennis, spa, sauna, hot tub, & washer/dryer
9.8 out of 10, Exceptional, (19)
"Very clean. Warm cozy home feeling. Walking in felt so clean and airy. It is a home away from home feeling."
All-season resort getaway with pool, tennis, spa, sauna, hot tub, & washer/dryer
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Resort condo with balcony & shared seasonal amenities - close to skiing
9.0 out of 10, Wonderful, (22)
"Great condo. Clean and easy process location good."
Resort condo with balcony & shared seasonal amenities - close to skiing
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⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
10.0 out of 10, Exceptional, (47)
"Jim's condo had everything we needed. Check in was seamless. Communication was great. Location was perfect. Our family had a wonderful time making memories. We'd definitely stay here again. Thank you Jim!"
⭐️Ski-On/Ski-Off COZY BEAUTIFUL MOUNTAIN CONDO 2-Bed/2-Bath with Fireplace
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
9.6 out of 10, Exceptional, (22)
"We’ve stayed at Winterplace several times, and this was the best in term of proximity to the hill (G building sits right next to the A-Quad drop off), cleanliness, upkeep (some WP units can be a little dated/beat), and layout. Was also well stocked with dishes, cookware, etc. Very satisfied."
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Spacious townhouse located in Killington, close to night life, Colony E28
9.8 out of 10, Exceptional, (12)
"This place was exactly as described ... great location, clean, close to Pico and Killington. Would definitely stay again!"
Spacious townhouse located in Killington, close to night life, Colony E28
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, (38)
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
9.6 out of 10, Exceptional, (53)
"Everything was great, good location close to Killington and the house had everything we needed!"
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
Newly Renovated Studio! Amazing Views/Location 3F9
9.8 out of 10, Exceptional, (7)
"Nicely renovated studio, well equipped, great location, perfect for one or two people on a short stay"
Newly Renovated Studio! Amazing Views/Location 3F9
Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning
7.4 out of 10, Good, (3)
"I have booked with VRBO for years. The booking said Ski in and out with a renovated surroundings. First … walking down 2 flights of stairs icy wooden walkway , across a icy parking lot, up a bank of snow and down in ski boots is not what I call ski in and out. Close to slopes is one thing! Second, my family cooks in for meals. The pots and pans were dirty and awful. Didn’t have enough silverware or glasses! Mattresses in master and second bedroom were old and uncomfortable. The unit was ok but...
Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning
Cozy 2BD/2.5BA Condo with Club Access
10.0 out of 10, Exceptional, (2)
"Had a great time!"
Cozy 2BD/2.5BA Condo with Club Access
Enjoy this spectacular 3 bedroom 3 bathroom Condo sleeping 8 Highridge B20
Enjoy this spectacular 3 bedroom 3 bathroom Condo sleeping 8 Highridge B20
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, (56)
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, (7)
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (13)
"Wonderful location located just south of the slopes. A bit of a walk to the lift but doable and fantastic trail to ski home. Very clean, loft area was a great addition. Very nice to have complimentary shampoo/conditioner/soap and dishwasher and laundry detergent. Everything we need for baking/meals. Lots of extra pillows!"
Trail Creek 33 | Condo in Killington
Location! Location! 1BR/1BA Steps to Mountain. 3E3
9.4 out of 10, Exceptional, (12)
"Location was great and the accommodations were perfect. The listing was a bit inaccurate in that the fireplace doesn’t work, the on site restaurant wasn’t open, no ability to get coffee or snacks, and parking was far from the unit."
Location! Location! 1BR/1BA Steps to Mountain. 3E3
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
8.8 out of 10, Excellent, (23)
"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
8.4 out of 10, Very Good, (7)
"Great location and the host was right on the money anytime I had a problem with question I was able to email them and they got right back to me. That’s the way to do it."
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views
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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.

Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (32)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (176)
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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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