Condo vacation rentals in Windsor County

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Popular amenities for Windsor County condo rentals

Weekly condo rentals

Guest favourite
Condo in Killington
4.91 out of 5 average rating, 141 reviews

2 bed-2 bath (6 max): walk to lifts and lodges

CharlesRating, 5 stars1 month ago
A wonderful home base for a wonderful Winter ski treat! Highly recommended, very comfortable and very well equipped. Super smooth check-in in a wonderful location.
Guest favourite
Condo in Killington
4.9 out of 5 average rating, 128 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

KateRating, 5 stars2 weeks ago
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!
Top guest favourite
Condo in Killington
4.95 out of 5 average rating, 229 reviews

Walk/2min Shuttle to Lifts 2BR @ Mt. Green Resort!

ErzsebetRating, 5 stars1 week ago
Very clean, cozy and spacious place to stay. Well-equipped kitchen, clean bed sheets and towels. Very easy access to Killington ski resort Ramshead Base. Tina is a great host!! I would recommend this apartment!
Condo in Killington
4.73 out of 5 average rating, 11 reviews

2BR condo, fireplace, balcony, pool, hot tub

RachelRating, 5 stars1 month ago
The condo was super accessible to Killington, with multiple restaurants nearby. The whole mountain experienced a power outage while we were there, but our condo got power back quickly, and the hosts had left flashlights and batteries! The one issue we had is that we have kids, and the second bedroom is on the second floor and there is NO door to close off the second bedroom. It attaches to an adorable alcove balcony, but it reduced the privacy in the second bedroom and also meant that the only way to make the room completely dark was to turn off the lights in the living room downstairs. It was not a big issue because our kids are older, but it’s not clear in the listing.
Condo in Killington
4.91 out of 5 average rating, 55 reviews

Starry Nights At KVR

ZoeRating, 5 stars1 week ago
Location is great - easy drive right on the access road to the slopes and to Killington restaurant area. Lots of space with 2 bedroom areas and 3 full baths plus a washer dryer in unit was super helpful. Susan is extremely responsive and instructions were clear and easy. Thanks!!
Superhost
Condo in Killington
4.83 out of 5 average rating, 23 reviews

Spring Ski and stay! Cozy 1BR/1BA Condo

TiffanyRating, 5 stars1 month ago
Stayed here for a long weekend. The condos location is prime since it’s so close to the slopes! Everything we needed was right there in the condo, plus the added fireplace was great to make the cold night so much more cozy! I cooked a couple times and the kitchen had all the basic essential I needed to get the job done. Bed was nice king size and comfy. The bathroom was a little bit small, and since it’s dated the shower could not stay hot for more than 10 minutes. I think the hot water tank wasn’t large enough to accommodate both me and my husband. We had to let the water regenerate for 30 minutes before the other one could hop in to shower. Overall a great stay!
Condo in Killington
4.72 out of 5 average rating, 43 reviews

Killington VT

WesleyRating, 5 stars1 month ago
Richard’s place was perfect for our stay! The condo was clean, cozy, and well-equipped with everything we needed. His detailed instructions made check-in, check-out, and navigating the area super easy. The location was fantastic — close to the slopes with convenient shuttle access. Richard was communicative and helpful throughout our stay. Highly recommend staying here for a great Killington experience!
Condo in Ludlow
4.94 out of 5 average rating, 100 reviews

Okemo Ski Condo, Steps from Trails. Modern & Cozy

ChristopherRating, 5 stars1 month ago
We had a great time staying at Maria’s place. Close to the slopes, super comfortable and clean, very responsive communication, and overall fun experience. We hope to be back!

Pet-friendly condo rentals

Superhost
Condo in Hartford
4.83 out of 5 average rating, 6 reviews

Close to Lake & Golf & Pool | Newton Village 2A

JessicaRating, 5 stars6 months ago
This lovely home had everything my family needed for a weekend away. The pictures and description of this home are very accurate. Highly recommend!
Guest favourite
Condo in Killington
4.96 out of 5 average rating, 130 reviews

Dog-Friendly Mountainside Escape/Pool/AC

ShaneRating, 5 stars1 week ago
Beautiful condo, nice location near the Sunrise lift and Bear Mountain. Very home like atmosphere in condo.
Guest favourite
Condo in Hanover
4.91 out of 5 average rating, 85 reviews

Walk to town - 2 bedroom condo

KathrynRating, 5 stars3 weeks ago
Loved staying here!!! Would 100% love to stay again!! So walkable and great hosts!
Guest favourite
Condo in Killington
5 out of 5 average rating, 11 reviews

Stunning Slopeside Condo at Mountain Green: 1BR

DavidRating, 5 stars1 month ago
This is a really neat property with a ton of personal touches. It feels like you are a welcome guest at a good friend's house. We have thought about being hosts in the future, this was a great example of how to handle a property!
Guest favourite
Condo in Hartford
4.9 out of 5 average rating, 42 reviews

Christian Street Condo with Screened In Balcony

TanikaRating, 5 stars1 week ago
Team ECEA was required to stay in the West Lebanon area for an extended period of time. We were able to stay at 3 different locations hosted by Wolter Group and each space was just what we needed and very convenient to the location we were working. They were always very responsive and and were a pleasure to do our business with.
Superhost
Condo in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars3 months ago
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.
Guest favourite
Condo in Killington
4.97 out of 5 average rating, 147 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

EileenRating, 5 stars1 month ago
Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.
Guest favourite
Condo in Killington
4.93 out of 5 average rating, 44 reviews

2 Bedroom / 2 Bathroom condo with Spa & Pool

DavidRating, 5 stars1 month ago
Catherine is a great host--very responsive and a clear communicator. Once Catherine notified us prior to our arrival we literally had no questions for her throughout our stay. She crossed every T and dotted each I before we walked through the door. The home itself was extremely comfortable and more than spacious enough for my daughter and I. And there was room for more (Next trip?). Location on Killington's access road makes anything you want or need just a short drive away. Nothing but fond memories of our stay at Catherine's.

Condo rentals with a pool

Condo in Killington
4.78 out of 5 average rating, 270 reviews

Come to Killington this summer!

SamuelRating, 5 stars1 week ago
Great stay. Location is prime, especially if you need some ski tuning at Black Dog Sports and want to be close to the mountain. Plenty of space and clean. Bed was a little firm but thats okay. Will be coming back in the future.
Condo in Killington
4.95 out of 5 average rating, 39 reviews

Seasonal Ski On/Ski Off 1BR Condo; Sunrise Village

KathrynRating, 5 stars2 months ago
We had a great weekend skiing and snowboarding at Killington. You can’t beat the location in terms of ease of access to the Sunrise lift (just know it only operates at peak season.) The restaurant and pool/hot tub area were an added bonus. The condo was as it was described. We had a great weekend and would return!
Top guest favourite
Condo in Killington
4.86 out of 5 average rating, 84 reviews

Mountain Oasis

CynthiaRating, 5 stars1 month ago
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!
Guest favourite
Condo in Killington
4.97 out of 5 average rating, 66 reviews

FUN 2BR/2BA Condo – Pool, Spa & Walk to Lift!

JanetRating, 5 stars2 weeks ago
Ryan’s pad was beautifully decorated and super comfortable. The beds were perfect, plenty of towels, paper supplies, toiletries, cleaning products and coffee! It’s easy to access and we used the masseuse and hot tub. Super close to Snowshed/Ramshead (5 minute walk maybe, we drove down to ramshead so we could have lunch in the jeep) and on the shuttle route. Ryan himself was kindly communicative. We would 100% stay here again if we get the opportunity.
Guest favourite
Condo in Mendon
4.87 out of 5 average rating, 53 reviews

2 Bedroom Pico/Killington Loft Condo at FoxHollow

MatthewRating, 5 stars2 months ago
Great stay for proximity to the slopes in Killington! The pictures also don't do this place justice as it's very nice! Will definitely be coming back
Guest favourite
Condo in Killington
4.85 out of 5 average rating, 13 reviews

Killington Getaway 2bed/1.5 bath

VictoriaRating, 5 stars1 month ago
It was a really great stay. Thank you!
Top guest favourite
Condo in Ludlow
4.96 out of 5 average rating, 51 reviews

3 Bedroom Castle Town Home

TomRating, 5 stars1 month ago
For our family of three this home fit us perfectly. You CAN certainly have more guests but it truly fit our needs. The set up was VERY spacious and cozy at the same time. The women at the desk are so kind and very good at their jobs. Not only did we feel at home when we arrived to our place, meeting them made us feel even more welcome. The castle was exquisite and an amazing experience in itself. The quaint town of Ludlow is a heart beat away with everything you need. All and all we can't say enough about how satisfied we are with Andy's home, the pricing, the staff and location! Our experience was amazing, memorable and we will be returning for sure next year! We are planning to come with our best friends next year & their kids because of your amazing home & our fantastic experience! 😁 Thank you again for opening your home to our family! The Baers
Superhost
Condo in Killington
4.83 out of 5 average rating, 53 reviews

Ski & Spa Winter Escape

EmmaRating, 5 stars1 month ago
Melissa's place was great for our group of 4 friend group skiing at Killington over the weekend! It was super easy to get to Killington to ski and cozy to come home to after a day on the slopes. We didn't get a chance to use the hot tub/spa but certainly would love to next time!

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