
Apartment holiday rentals in Windsor County
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Top-rated apartment rentals in Windsor County
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Steps away from lift- Okemo 1B
Excellent location for skiing. I do not think I have ever stayed this close to the lift. Being able to stop by the apartment for lunch, or simply to warm up is a huge perk. It can be a bit loud from the lift and the groomers but it wasn’t an issue for us. The apartment is very comfortable for 2 adults and 2 kids.

Welcome to Ava's Place!
We had a very nice stay at Ava’s place. The place is very clean and cozy. It is also more spacious than we thought. Diane and Ava were very nice and left us with welcome gifts which we really enjoyed. The room had everything we need from coffee, tea, to fabric softer. The location is also convenient. It is about a 15 min drive to Okemo mountain resort and 18 min to Rutland with some dining options.

Cozy Green Mountain Village Apt
Was in need of a place to stay in Rochester for a wedding down the road from the main part of town and I couldn't have picked a better spot for the weekend. It's a cozy little apartment that has all the simple things you need and it's walking distance to some small town jems to shop and eat at. If I ever want to come back to VT from Boston for the fall, or to escape the city life, I know what would be my first pick would be. :)

49 River Street
Immaculate place. Everything you might need! Very charming town. Close to Green Mountain and Appalachian trail hiking. This was our second stay here and we love it. Also, definitely go to Sweet Birch coffee shop while in town. :)

Peaceful Woods- Suite with Private Entrance
This was a wonderfully peaceful place to stay for a girls weekend! Carol and Steve’s garden is absolutely stunning. The homemade blueberry banana bread was such a delicious and welcoming treat. Would stay here again in a heartbeat!

Two bedroom private suite- Woodstock/Barnard, VT
We would highly recommend Corinna’s place to anyone. Our friends and I felt right at home and had a lot of room to move throughout the property. The location is above a Tavern with amazing food. The property itself is spacious, clean, and full of amenities. We ended up getting snowed in for a full day and were able to enjoy the property and turn it into a game day. Loved the place and enjoyed our stay!!

Charming Killington get away with pool, sleeps 4
Great place to stay for the weekend! Super close to Pico and Kilington mountains. Would highly recommend!

A Hikers Retreat
Bernie’s place was perfect for our stay! We booked it for a last minute ski trip to Killington and the location was great. Although we didn’t dine out at all, the place was very close to town with restaurants and shops. It was just two of us so the space was great! Everything was very clean and well stocked. Would definitely stay here again!
Private apartment rentals

Tunbridge Home with a View
We had a wonderful weekend stay at David and Beth's home. We had a friendly greeting upon arrival (as well as delicious homemade cookies and maple candies!) David and Beth's home is attached to the apartment but it was quiet and they were unobtrusive. The Tunbridge area is beautiful - quintessential VT! The property is tucked away a bit (SO Vermont!) but our all wheel drive car handled a little bit of late February mud and rolling hills without a problem. We prefer to eat in and brought some food to prepare in the well-equipped kitchen (however we did go to a great burger bar for lunch in Royalton about 20 mins away). The apartment was warm, cozy and comfortable - a perfect meeting place for us and our two adult children - just what we were looking for! Thank you David and Beth - we may see you again next year!

Cozy VT 1st floor apartment
We have stayed here before. The apartment was comfortable, very clean, quiet and has everything you need. We would definitely recommend !

Okemo Mountain Retreat
Perfect location for Okemo - true ski-in ski-out - literally steps away from the Clocktower base lodge and Lift B. Amazing to be able to take lunch break back at in the condo. The unit was clean, roomy, well-furnished - pictures are accurate. Beds (Qn and bunk) are located in the same room but felt like it could work easily for close family/friends. Lucky to find the place for a late season trip up from NYC. Thanks for a wonderful stay and I look forward to future stays!

Nice, Large Modern Apartment
Darcie’s house is a great place to stay in Rutland! It is clean and comfortable, furnished to a high standard. The location is excellent – handy to everything in downtown Rutland. The street is quiet. Best of all, Darcie is very responsive, answering quickly, and gracious to travelers with last minute requests. Highly recommended.

Cozy Corner Nook
Stayed for a snowboarding trip at Killington and a day at Sugarbush. 20 mins from Killington in the center of town below. 1 hour from Sugarbush. Great stay

Best Location in Downtown Killington
Extremely quick to respond . Just wanted to let them know of a few housekeeping issues, not expecting anything to be done, but property management was immediately called and they sent someone over to remedy what they could. Very quiet and got to see a bear. It apparently was off season and most places were closed. If you use washrags, bring your own as property management does not supply them. The beds and furniture were very comfy.

2 BR Condo, 5 minute walk from Dartmouth campus
My friend and I stayed in this lovely home when visiting Hanover for a business school reunion. We are both moms and it was the perfect place for a peaceful escape from our busy lives! It was a quick, easy walk into town and the right balance of convenience and quiet. Also extremely well stocked! Would definitely recommend and stay here again.

Sweet apartment near downtown Woodstock
I had a great time staying at Sharon’s. You have a private entrance and a place to park. The kitchen is equipped with everything you will need to make a meal. A full size fridge, stove and a dishwasher. Plenty of room for you and a few friends. The bedroom and bath come with all the things you’ll need including hair care products, plenty of large fluffy towels, a hair dryer and an iron to name a few. Sharon has also provided Netflix in the apartment, but I don’t think you will spend too much time watching tv. You are only a few minutes from downtown Woodstock where you will have plenty to do either shopping, walking or dining in an amazing restaurant. I definitely will be back.
Apartment rentals with a hot tub

Cozy Quarters
We had the best time staying here for a ski weekend! Super convenient location. Clean and comfortable condo. Can’t go wrong! Heather is responsive and friendly.

Cozy Studio/Onsite Spa w/Pool,Hot tub
We loved staying in this cozy little room for the weekend. The spa was such a nice addition we went every day!

Dog heavenly! Private, beautiful and relaxing.
Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

Mojo Dojo Winter Casa Condo at Mountain Green
An absolutely lovely stay at this property. Extremely scenic, peaceful and green. There is much thought put into the decor of the property. It’s well furnished and decorated with excellent kitchen and bathroom facilities. Ample space and comfortable bedding. Terrific location. This is my third time at Killington from Australia and this has been the best property I have stayed at in Killington. Thank you.

Cozy Killington Condo
We loved how close the hot tub and pool were to the condo.

Cozy 2-BR Winterplace Condo Steps from Okemo Mtn.
Location was perfect for my 2 boys and myself. Pool and hot tub was right across the street. On the opposite side of parking lock was access to lift. Perfect location for what I needed. Noah left plenty of recommendations for local spots to check out. Highly recommend!

Condo at Mountain Green
Simple and basic perfect for a ski weekend at the mountain especially since pet friendly. Kristin was very responsive and helpful throughout the weekend whenever we needed anything. Would highly recommend this stay.

New Resort Condo Close to Lifts
perfect host! communicates well & perfect area!
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dorset Field Club
- Autumn Mountain Winery
- Fort Ticonderoga
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Bretwood Golf Course
- Brattleboro Ski Hill
- Hooper Golf Course
- Fox Run Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Things to do Windsor County
- Food and drink Windsor County
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