Guesthouse holiday rentals in Windsor County

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Popular amenities for Windsor County guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars3 months ago
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.
Guest favourite
Guesthouse in Strafford
4.93 out of 5 average rating, 143 reviews

Spacious Country Guesthouse

PederRating, 5 stars2 days ago
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.
Guest favourite
Guesthouse in Chester
4.92 out of 5 average rating, 179 reviews

Historic Carriage House-20 Min to Okemo-Magic MTN

ShaniRating, 5 stars2 weeks ago
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!
Guest favourite
Guesthouse in Woodstock
4.98 out of 5 average rating, 243 reviews

Cozy Little Spot (Self Check-in)

ChrisRating, 5 stars2 days ago
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!!
Guest favourite
Guesthouse in Springfield
4.85 out of 5 average rating, 374 reviews

Connecticut River-Cozy Cottage

DannyRating, 5 stars5 days ago
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.
Top Guest favourite
Guesthouse in Hartland
4.95 out of 5 average rating, 993 reviews

Yurt In The Woods - Private Refuge

KristieRating, 5 stars2 days ago
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.
Top Guest favourite
Guesthouse in Hanover
4.97 out of 5 average rating, 58 reviews

Private guest-room 1 mile from Dartmouth

DavinRating, 5 stars8 months ago
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

Top Guest favourite
Guesthouse in Mount Holly
4.96 out of 5 average rating, 67 reviews

Moon Acre Farm Green Mountain Oasis - near Okemo

KentonRating, 5 stars3 weeks ago
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.
Guest favourite
Guesthouse in Hartford
4.87 out of 5 average rating, 115 reviews

Addie's Place

BridgetRating, 5 stars5 days ago
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!
Top Guest favourite
Guesthouse in Lebanon
4.95 out of 5 average rating, 118 reviews

Private guesthouse in Lebanon

BriannaRating, 5 stars3 days ago
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!
Top Guest favourite
Guesthouse in Reading
5 out of 5 average rating, 30 reviews

Peace & quiet at Comet Farm

XiangchengRating, 5 stars3 months ago
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!
Top Guest favourite
Guesthouse in Chester
4.94 out of 5 average rating, 17 reviews

The Lodge

JaniceRating, 5 stars8 months ago
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.
Guest favourite
Guesthouse in Chester
5 out of 5 average rating, 17 reviews

New in town Chester Retreat, 14 Miles to Okemo!

VeronicaRating, 5 stars3 months ago
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

Guesthouse in Killington
4.63 out of 5 average rating, 8 reviews

Slopeside Estate Guesthouse: Ski On/Off, Hot Tub

DennisRating, 5 stars4 months ago
Great place, beautiful house. Easy short walk to the trail.
Guest favourite
Guesthouse in Andover
4.89 out of 5 average rating, 106 reviews

Quiet Self Contained Apartment in Vermont Hills

StanleyRating, 5 stars3 months ago
Stephen's place is conveniently located to Okemo and amenities are perfect for a weekend trip.
Guesthouse in Weston
4.15 out of 5 average rating, 13 reviews

1BR dog-friendly mtn cabin with fireplaces

IanRating, 5 stars15 months ago
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.
Top Guest favourite
Guesthouse in Plymouth
4.97 out of 5 average rating, 106 reviews

Quiet Couples Retreat near Killington and Okemo

LeighRating, 5 stars3 months ago
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.
Top Guest favourite
Guesthouse in Cavendish
5 out of 5 average rating, 13 reviews

Brand New Village home in Cavendish, VT

LisaRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in Ludlow
5 out of 5 average rating, 5 reviews

The Black Sheep Barn

MichaelRating, 5 stars11 months ago
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.

Destinations to explore