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

Cute Cool Cabin! Plymouth, Vermont.
Alecia and John were meticulous hosts from the well curated guide book to their responsiveness when we had questions. All made for a wonderful family fourth of july! We look forward to returning.

Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
We definitely have never stayed in a rental that was so CLEAN! Aside from the labels, it felt as if we were not staying at a rental property at all. When we go away, it’s nice to stay somewhere that’s close to as nice and comfortable as home. We were warm and cozy. The house had everything and way more than we needed and we would like to see how beautiful it would be in the Summertime. The house was spacious and we loved the history and charm that it possesses. The hot tub was a major draw and sparkling clean also. It snowed practically the entire visit and felt private with all the trees surrounding the property. A huge perk was the proximity to Okemo and Killington for the boarders in our group. With the looks of the Volleyball net and court, presumably the owners are fans of the game! Bravo, Alecia- we thank you for your hospitality!

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.

Country Chalet, HotTub, 8 Mins to Skyeship Gondola
Perfect place for a ski weekend with a group of friends. House was exactly as described, check in was extremely simple, and all the amenities were in full working order and easy to use (special shout out to the hot tub which was amazing after a day out on the mountain). Location is less than 10 minutes from the Skyeship gondola, less than 20 from the main Killington base areas, and easy to find just off of the main road. Overall we had a great time and would 100% stay here again in the future.

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.

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.

“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!

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.

Apple Branch Guest House
This was a perfect stop for a night or two in peaceful surroundings. It was easy to find and had everything you could need! The beds were super comfy!

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!
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.

Vermont Hillside Garden Cottage
We really loved our stay at the cottage! The cottage is tucked away on a quiet dirt road in an absolutely beautiful, private setting. The space was perfect for our needs and we would definitely stay again!

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
David’s place was stunning and a wonderful getaway for our group of 4. Location is quiet but not too far from some great spots for food, activities and outdoors. A well stocked kitchen, super responsive host, and a beautiful and updated interior made this a comfortable and fun place to stay and we can’t wait to come back!

The Vershire Fortress
What a gorgeous space, nestled in the most beautiful landscape you can imagine. Everything is exactly as billed - the space is lovely, updated, clean, and modern. The home overlooks spectacular views of fields, forests, and mountains in the distance. The horses pastured in the field behind the house were an added bonus!

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
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Autumn Mountain Winery
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Brattleboro Ski Hill
- Veterans Memorial Recreation Area Ski Hill
- Fox Run Golf Club
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