
Monthly Rentals in Windsor County
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Superhost

Apartment in Windsor
4.71 out of 5 average rating, 28 reviewsQuaint Vermont Village Apartment 2
AndreaRating, 5 stars2 months ago
I’ve stayed at Alissa’s places before. This was the first time at this one and it was the same great experience. Location has easy access to highways and amenities. It was quiet, even with the occasional plow. Thanks Alissa! As always, it was great!
Top guest favorite

Chalet in Woodstock
4.98 out of 5 average rating, 104 reviewsFalcon House: VT Chalet w/Sauna, Bike to Village
AngieRating, 5 stars1 month ago
Falcon House Chalet is a beautiful home in a stunning setting. Matt and Kat were fabulous hosts, responsive, friendly and professional. Matt cleared the driveway and walkways of snow as needed and gave our group wonderful hike recommendations. The chalet is a woodworkers dream with beautiful wood throughout the home. The wooden spiral staircases are easy to maneuver and attractive too. The main level bedroom is quite small but quiet and private. The upstairs main bedroom is open to the den but we really could not see anyone up there. If you prefer a door, there is not one. The lower level has a nice futon, TV and quiet environment. There is a washer and dryer which is very helpful with the hiking and snow shoeing. The outdoor sauna is a must if you can run quickly through the snow! There are so many positives that I could continue to write. If you visit, I wrote detailed noted in the guest book that would be helpful.
Top guest favorite

Home in Woodstock
5 out of 5 average rating, 47 reviewsHiker’s Hygge on 21 Acres and Aqueduct Trails
PhoebeRating, 5 stars2 weeks ago
Kevin and Emily's home offers a cozy launching point for adventures around Woodstock and the upper valley area, with a setting that is incredibly peaceful and picturesque. Kevin was very clear with directions and extremely responsive while we were staying at the house. He also generously agreed to a delayed checkout, so my daughter and her friend could enjoy a last dose of winter fun before our departure. The house had everything we needed, including two sledding saucers for snow play, and a gas stove to warm up next to after coming in from the cold. One small detail to note--the lower bunk bed has a low/confined ceiling that can be tricky for taller kiddos. Overall, we had a lovely stay and would definitely come back to explore the trails in another season!
Top guest favorite

Home in Woodstock
5 out of 5 average rating, 13 reviewsFabulous Log Home in the Woods
GailRating, 5 starstoday
This was a lovely home and we really enjoyed our stay there. Because the weather was unseasonably warm during our visit, the road to the house was quite muddy and slippery (more typical April weather) and so a bit difficult to navigate, even with all-wheel drive and 4-wheel drive vehicles. However, this comes with the territory on dirt roads in Vermont during their spring season. The setting itself is beautiful and well-worth having to slow way down to get up to the house!
The comforts of home and great monthly rates
Amenities and perks for longer stays
Furnished rentals
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Special rates for long-term vacation rentals and a single monthly payment without additional charges.*
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- Rentals with an accessible height bed Windsor County
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*Some exclusions may apply in certain geographies and for some properties.