
Condo vacation rentals in Windsor County
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Top-rated condo rentals in Windsor County
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Castle Retreat – Pool, Spa & Mountain Adventures
Lovely condo - perfect for Okemo and about 35 mins from Killington. We did both mountains over a long weekend. Loved the 2.5 bathrooms and 3 bedrooms for our family of 4 (two adult sized teenagers!). Would work for two families as well as bedrooms have attached bathrooms. Everything I needed for cooking was there - pots, pans, strainer and all appliances worked perfectly. The radiant heat in the master was an added bonus! You will definitely need snow tires or AWD if it snows as its on a hill but the condo paths are well maintained.

Bright & Cozy condo with AC, Tennis, and Pool
very happy with our stay. Perfect accommodations. Everything was clean and sanitary. The host was communicative and friendly. We needed a hiking suggestion and he was great. Very personable through email. We will contact him again to stay there next year.

Hike Bike Golf low $ 2 Bedrm 2 min Mtn & Apres
Looks exactly like the photos. It is close to the ski slopes, and spacious for a group of three.

Condo on Quechee Golf Course with Private Feel
It was so great staying at Corey’s place! It was just liked described and it was a great launch pad to explore Quechee and the surrounding area. We enjoyed it so much and would love to go back!

Perfect Getaway! Modern & Convenient to Everything
Great Place to stay. It’s small yet enough for two people which is what we wanted. It is very clean and had all basic cooking stuff. It is a cute little place to spend a weekend in a serene location. We had a peaceful stay. Jim patiently responded to all our questions before checking-in. We would love to stay here again and would definitely recommend friends.

Luxe Trailside Ski On/Off. Next to hot tub
Responsive host!

Pico G-203 Ski on/off Condo. Note: No Air Con.
A wonderful location that was practically ski-in/ski-out to the Pico ski resort and about a 15 min drive to Killington ski resort. The pictures accurately represent the property. Jane and Darwin were exceptional hosts, answering every question promptly. We would definitely stay again.

3-Bedroom Condo in the heart of the Village @Okemo
Korey’s place was really perfect for our stay! It was clean, comfortable, well-appointed, and super convenient to Okemo and all the area restaurants and amenities. And Korey was very kind, helpful and easy to reach if needed. We would definitely stay here again!
Pet-friendly condo rentals

Year-round Fun in VT: Wonderful Country Apartment
This was our first Airbnb trip as a family with 2 young kids, and was our best trip to date. We all appreciated having such a cozy space to come back to during our 3 night stay in Vermont. You can’t beat the location being across the street from Long Trail Brewery, right around the corner from a general store with basic groceries, and right in between Killington and Woodstock. Upon arrival (and each night of our stay), the property was well lit with string lights giving it a festive feel and making it easy to find when we first arrived at night. Alexandra’s instructions for how to access the property were easy to follow. The space had everything we needed to make us feel at home - a step stool for the kids to brush their teeth, a well stocked kitchen, and bathroom essentials that we had forgotten- even some welcome snacks and bottles of water. We appreciated the cozy bedding and blanket baskets as the rooms with window AC units were drafty at times. We would happily rebook again!

Farmhouse Beauty Minutes to Woodstock & Skiing
Wonderful stay. Immaculate. Very cozy and close to the slopes and to Woodstock. Highly recommend this place.

Fully walkable 2BR condo in Ludlow’s village!
We had the pleasure of staying at Ryan’s place on Tapper Street in Ludlow, from August 31 to November 30, and it was absolutely fantastic! The house was the perfect relaxing retreat. The living room was super comfortable—ideal for cozy nights watching TV. Our kids especially loved the bunk beds, which were a big hit! The house was well-equipped with all the amenities needed for a long stay, making it feel like a home away from home. Ryan was a wonderful host, always responsive and helpful. His recommendation to try DJ’s Restaurant was spot on—the Cajun blackened salmon was incredible! We can’t recommend this place enough and would love to stay again in the future. Thanks, Ryan, for a wonderful stay!

Cozy Fireplace, Large Deck with Views | Saltbox 9A
Great location. Close to Quechee club and Simon Pearce. Clean and comfortable unit.

Walk to town - 2 bedroom condo
Wonderful place to stay near campus. Very comfortable. A great option to get your own space near Dartmouth

Christian Street Condo with Screened In Balcony
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.

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

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
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.
Condo rentals with a pool

Book now to Golf Fish Hike Bike Vemont!
We enjoyed our stay at this condo! It was exactly as represented in the listing, and very close to the Killington lifts. The condo is pretty small, but that was okay since it was cozy and had what we needed.

NEW Killington Studio: Great Location! Comfy. 431
Nice cheaper lodging on the access road

Winterplace - Steps away from Slopes
A short walk to the ski slopes. The host was very helpful and proactive recommending where to go to ski based on your skill level. The place is functional and spacious. my favorite two things was proximity to the ski lifts/slopes and very comfortable mattresses/beds. When I ski, I need a nice rest and this place is a great for that. I would recommend this place and I would stay at Andrew's place again. Thank you Andrew for a great vacation!

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Killington Summer Retreat | Bike • Golf • Pool
This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it

Newly renovated ski retreat at Killington
Wayne is super nice, friendly, and responsive. He gave me heads up note on check-in day when the main road (Killington Access Road) was closed due to downed trees&wires. He also helped me confirm the parking spot in late night when I arrived late. The place is cozy and clean. There’s a number of good restaurants and taverns nearby.

Walk to lift, Ski home, Sunny with loft
We really enjoyed our stay at Brent’s place. It’s an end unit and top floor so it was quiet with lots of windows and natural light. Everything was exactly as described. It was very comfortable for our group and we had everything we needed. There’s a small stream that runs along the back. I really enjoyed the idyllic view with my morning coffee. Brent was a great host. We’d definitely like to return!

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf
Location was perfect! The weekend shuttle to Snowshed was very convenient and the trail to ski home was an easy way to get back. Also loved the spa amenities after a long day of skiing. Will definitely try to come back to this place for future visits!
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Tenney Mountain Resort
- Dorset Field Club
- Autumn Mountain Winery
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Brattleboro Ski Hill
- Bretwood Golf Course
- Hooper Golf Course
- Cozy Cottages & Otter Valley Winery
- Fox Run Golf Club
- Veterans Memorial Recreation Area Ski Hill
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