
Guesthouse holiday rentals in Windsor County
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Top-rated Guesthouses in Windsor County
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Popular amenities for Windsor County guesthouses
Family-Friendly guesthouses

Macintosh Hill Farm
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.

Spacious Country Guesthouse
It was a great stay; the location is very peaceful and beautiful outside with a nice little hike nearby. We would definitely stay there again. The host was very nice and checked in each time we returned to find out if we needed anything.

Historic Carriage House-20 Min to Okemo-Magic MTN
We stayed here while attended to a wedding. The place was great for us as we brought our parents to babysit our baby while went to the wedding. The space was great for us - 4 adults and a baby, and we didn’t use the third bedroom. Big kitchen included all the things we needed for light cooking. The hosts kindly left some basic ingredients like oil, sugar, and much more and it was fantastic as this things are always annoying to carry with you when you go for couple of days. One thing to note is that there is no cooling system in the carriage house, if it gets hot it might be something to consider. Highly recommend for friends/family getaway!

Cozy Little Spot (Self Check-in)
I can’t say enough good things about this place! I don’t think the pictures do it justice! If you are looking for an authentic Vermont experience, look no further, the cabin is so dialed, it’s in an idilic setting, super quiet and a ton of privacy but very close to town and anything you’d need. In the summer, at night, leave the windows open and enjoy the sound of the brook and stream directly below the cabin! Highly recommended!!

Connecticut River-Cozy Cottage
Very quiet. I slept very well. The river runs immediately behind the cabin and is scenic. It's only a few miles from town, which is nice given that the cabin feels secluded. Reasonably priced. It's a good place for a single person or couple.

Yurt In The Woods - Private Refuge
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.

Private guest-room 1 mile from Dartmouth
Clean and comfortable space for 2 in Hanover, New Hampshire close to downtown. The accommodations were as advertised in the listing.
Guesthouses with a patio

Moon Acre Farm Green Mountain Oasis - near Okemo
Heather and Peter were delightful hosts. We enjoyed the beauty and peace of their surroundings. The comfy bed overlooked a pond which we liked. The kitchen hot plate and large countertop oven worked well for making full meals. We even made a homemade deep dish pizza in the oven which turned out really well. The large refrigerator was stylish and quiet. It was good to have a full sized washer and dryer. The living room furniture was really clean which was great. The hosts also gave us a tour of their property.

Addie's Place
Stephanie's place was an oasis of peace and calm while assisting my father getting surgery at Dartmouth Hitchcock. I actually took the bus to the area and the local free bus is great, with a stop right at the end of the block. really enjoyed sitting in the swing and watching the hens!

Private guesthouse in Lebanon
We had a great stay at Nathaniel’s place. The neighborhood is peaceful and quiet, which made for a restful night’s sleep. The town is charming and just a short half-mile walk away, with plenty of cute restaurants to explore. Parking right in front of the house was super convenient, and check-in was a breeze. We’d definitely stay again!

Peace & quiet at Comet Farm
This is an absolutely gorgeous place to stay in Vermont and we loved it!! The living room and bedrooms are all elegantly decorated and also very cozy. More importantly, Madeline and Parris are the best hosts we have ever had. We came to Vermont for a ski trip and ran into some snow-related issues on our first day. Madeline and Parris were very responsive and offered tremendous help to us. Overall, a beautiful house with great hosts for an amazing stay!

The Lodge
Beautiful home and property. Even in the rain the view of the mountains was picture perfect. Easy to get to other areas of VT. Comfortable beds and roomy couch/living space.

New in town Chester Retreat, 14 Miles to Okemo!
Jeff’s place was perfect for our two family ski trip. Our kids especially enjoyed the basement and there was plenty of room to spread out. Well equipped kitchen and big open dining/kitchen/living area were great for cooking and eating together. We had a great stay!
Guest house rentals with a washing machine and dryer

Slopeside Estate Guesthouse: Ski On/Off, Hot Tub
Great place, beautiful house. Easy short walk to the trail.

Quiet Self Contained Apartment in Vermont Hills
Stephen's place is conveniently located to Okemo and amenities are perfect for a weekend trip.

1BR dog-friendly mtn cabin with fireplaces
Options are limited when we travel our with two dogs so we felt very fortunate to find the home in Weston. It was perfect for the two of us and our two dogs. The home had most of what you would expect as far as extras and everyday items. We loved the area we were in and the proximity to Londonberry and southern resort mountains. I would recommend the home to anyone with a small group. We will rebook next year if the cost doesn't increase.

Quiet Couples Retreat near Killington and Okemo
My daughter and I had a great stay at Rose’s place. The kitchen was clean, and we were very close to the Skyeship gondola at Killington. We enjoyed watching tv with the electric fireplace keeping us warm and cozy.

Brand New Village home in Cavendish, VT
Great place! We were traveling with our dog and felt right at home. Honglian’s place has everything you need for a peaceful vacation in Vermont!

The Black Sheep Barn
Stayed here during a summer trip with a family of 4. Amazing location - one block off of downtown and one block from Shaw's. Parking / check-in / everything was easy. Place was super clean and all appliances / equipment / linens / etc. were new / lightly used. Only potential issue was that the first level ceilings are pretty low, but If you're under 6'5", you will not have any issues. Communication with Nancy was great and all-in-all highly recommend / great value.
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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
- Fort Ticonderoga
- Autumn Mountain Winery
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Brattleboro Ski Hill
- Fox Run Golf Club
- Veterans Memorial Recreation Area Ski Hill
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