
Cottage vacation rentals in Windsor County
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Top-rated cottage rentals in Windsor County
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Popular amenities for Windsor County cottage rentals
Cottage rentals with a hot tub

2 person SunCottage - Hot Tub Solar Geothermal
The house was beautiful and had a bunch of nature space and can tell is very kept up and taken care of. The house inside is beautiful and clean. The hot tub with the nature view is amazing. Deff would give this place a 10/10 and recommend to people looking for a private and peaceful area. Only thing is no service if not from area and restaurants and grocery stores are alittle far out but other than that great place to stay!

NEW Guest Cottage on 23 Acres
We had such a great weekend at the Revival. Mark and Dana did an amazing job with this place. The house is gorgeous and so clean. The view is spectacular, and they provide you with so many activities to enjoy on the property. Close enough to be able to walk into Ludlow. This place really has everything you could possibly ask for. We are very much so looking forward to going back.

Vt Summer Getaway: Hot Tub, Golf Hiking & More!
Great house with plenty of space and beds. Living room had ample couches and great for our group to hang out there with the fireplace and hot tub off the back deck of kitchen. Kitchen had all necessary cooking pots/pans/utensils. Easy communication with the hosts and would return.

3BR lakefront with dock, swim platform, & firepit
This was our second time here, and we loved it just as much as we did the first time. Our dog really enjoys it as well!

Andas Hus: Little Luxury
Staying at Andas Hus was an Airbnb experience on another level. This little cottage has everything that you could ever need for an extended getaway- we did so much cooking, wandering, made full use of all of the tech, and enjoyed the hot tub for several nights. We had four adults sharing the cabin and it was more than enough room for us. Matt was super responsive and kind when we had questions about the stay. I'll absolutely be recommending Andas Hus to any of my friends and relatives looking for a New England getaway, and maybe we'll be back someday!
Pet-friendly cottage rentals

“Celia” room with meditation nook
Always a pleasure to stay at Hope’s place. Feels like home away from home.

The Mendon Cottage: Cozy Home. Killington / Pico
Place is exactly as advertised. One of our party was a non-skier (aka designated driver), which made the location even better. A couple of minuted to Pico, 10 minutes to Killington and 10 minutes the other direction to Rutland with all the conveniences of town.

“Matisse” bedroom in a country cottage
Hope’s Vermont cottage was fantastic. We were greeted by Zephyr (friendly cat) and Hope upon arrival. Her place was easy to find and Google maps took us right to the cottage. I did forget to look up the check-in instructions before getting there and found out I had no cell service with Verizon upon arrival. Even with no instructions, Hope’s cottage was easy to navigate to the front door and Hope was extremely welcoming. The cottage was immaculately clean and the vibe was homey and warm. Woke up to beautiful mountain views. Definitely would stay again in Hope’s idyllic country cottage!

Cozy COTTAGE- ski, swim, hike, foliage, near Okemo
The surroundings were beautiful and we loved watching the sun set over the mountains. The cottage was very clean and we really appreciated how well set up the kitchen was. Ron was friendly and responsive. We enjoyed finding swimming spots, local hikes and maple ice cream. We highly recommend the cottage and hope to return someday!

Vermont Country Cottage(Near Village w/Magic View)
The little white cottage was lovely with everything we needed for a comfortable relaxing weekend. Like every other weekend this spring...it rained...but the cottage was still bright and cheery. So much to do , see, and eat so close by. We'll be back!

VT Winter Getaway
Stayed at Nicole’s cottage for a long ski weekend with my wife and pup. Exactly what we were looking for in regards to a private, clean, secluded getaway for a few days. She had the heat turned up (gas fireplace) which was welcoming for our arrival in the cold. Nicole was great in touching base before and during the stay making sure everything was in order. She also shared tips on local shops/eateries making it easy to prearrange. Good proximity to slopes. Will look to stay again in the future.

Lakeside Cozy Cottage. Peaceful and Serene.
Wonderful escape from city life. This place is the epitome of serenity and relaxation. Ellyn is a wonderful, communicative host. Lots of hikes, lake activities and breweries made this a great stay for us. Go unplug here. Can’t beat the morning view on the lake.

Antique Ludlow Farmhouse - 12 minutes to Okemo
The host is very responsive and ensures that you are all set with the Wi-Fi and move in process. Directions to the property are clear and concise. The house is beautiful and spacious.
Private cottage rentals

Moon Beam Cottage--A cozy and welcoming retreat
We so enjoy staying at Melissa’s place. It has everything you could need and is an amazing location. We discovered the catamount xc trail is only a short distance away.

Comfortable White Cottage
Mary’s place was very quaint. Easy to get into. She left wonderful directions. Very clean. She had a lot of little extras that made you feel like home. She has true passion for flowers that was evident around the outside of her home. Absolutely beautiful It was fantastic to watch the birds interact with the flowers.

Ludlow Lakefront Home
We felt right at home in this lovely rustic cabin on the lake. We had to work with Thomas to solve some unfortunate complications during our stay, including a dead rodent in the sink, a lack of sheets and towels, and taking our trash with us. However, we loved the home and had a wonderful weekend in the area. Thank you!

Bright & Homey 3 bedroom near Killington & Pico
We enjoyed our stay at Madelyn’s place for our weekend ski trip. It was conveniently located close to Killington and was fairly spacious.

Riverside Cottage, Campanoosuc North
We really enjoyed the cottage next to the river. It was during Xmas break so quiet and snowy. You can hear the water current of the river out back, so it had a peaceful feeling. The interiors were just renovated so felt like a brand new home. The detailing was very well done and felt more like a home than an Airbnb. We definitely recommend it for a family as there are two bedrooms and a loft with 2 beds. David was very responsive so no worries. Also the area has nice Vermont towns to visit. Hanover, NH is nearby - home of Dartmouth College.

Lake Fairlee Porch Views from The Edgevale Gem
Olivia is a wonderful hostess. We have rented properties from her in the past and have always been happy with our stays.

The Vershire Fortress
What a delight! I was here to get away and write for a few days, and it was exactly what I needed. beautiful views, comfortable, cheerful, and elegant. It has everything you could need, and it was all easy to figure out. The only issue I had was the drive to and from the house bc it is peak mud season and the roads were in rough shape. I was really glad I had the recommended all wheel drive car bc you slide around quite a bit otherwise.

Ski cottage near Okemo, Bromley, Stratton
The place was just as described - cute as a button. The location was close to the ski mountains and had plenty of room to spread out! The kitchen was well appointed and the kids loved the triple bunk room. We will definitely be back.
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course
- Bretwood Golf Course
- Cozy Cottages & Otter Valley Winery
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