
Windsor County long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Bookabach takes the hassle out of booking monthly rentals in Windsor County. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Bookabach. Many long-term rentals in Windsor County are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Windsor County
Showing deals for:8 Feb - 8 Mar
Image gallery for Renovated 19th century farmhouse with swimming pond in private, bucolic setting

Renovated 19th century farmhouse with swimming pond in private, bucolic setting
Strafford
Image gallery for Winter Lore — 26 Private Acres, Game Room, Hot Tub & Pet-Friendly Near Killington

Winter Lore — 26 Private Acres, Game Room, Hot Tub & Pet-Friendly Near Killington
Mendon
Image gallery for Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

Pond View Cabin-Rustic 2 Bedroom-Sleeps 4
Chittenden
Image gallery for Enchanting 4-bedroom cottage with a view in Weston

Enchanting 4-bedroom cottage with a view in Weston
Weston
Image gallery for Far Enough, An Old World Vermont Estate

Far Enough, An Old World Vermont Estate
Brandon
Image gallery for Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!

Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
Chester
Image gallery for Spacious on Mountain 3 bedroom Condo available for Seasonal Rental.

Spacious on Mountain 3 bedroom Condo available for Seasonal Rental.
Killington
Image gallery for Carriage house in the village of Woodstock

Carriage house in the village of Woodstock
Woodstock
Image gallery for 5 miles to Okemo/Ludlow, 25 Acre Playground, Great Ski or Summer Rental

5 miles to Okemo/Ludlow, 25 Acre Playground, Great Ski or Summer Rental
Cavendish
Image gallery for Exquisite Log Home with views near Woodstock, Vermont

Exquisite Log Home with views near Woodstock, Vermont
West Windsor
Image gallery for Okemo Family Friendly Getaway

Okemo Family Friendly Getaway
Andover
Image gallery for Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Weston
Image gallery for Spacious ski house 5 minutes from the mountain / lifts. Great for hosting!

Spacious ski house 5 minutes from the mountain / lifts. Great for hosting!
Killington
Image gallery for ROMANTIC SPIRITUAL FAIRYTALE EUROPEAN TYPE COWBOY/INDIAN CASTLE

ROMANTIC SPIRITUAL FAIRYTALE EUROPEAN TYPE COWBOY/INDIAN CASTLE
Randolph Center
Image gallery for The Chairlift House · Walk to Mountain Top Inn · Stunning Lake & Mtn Views

The Chairlift House · Walk to Mountain Top Inn · Stunning Lake & Mtn Views
Chittenden
Image gallery for Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs
Ludlow
Image gallery for Picturesque 3-bedroom lake house with WiFi in charming Mt Holly, Okemo Mountain

Picturesque 3-bedroom lake house with WiFi in charming Mt Holly, Okemo Mountain
Mount Holly
Image gallery for Waterfront Ponds, Beautiful , 51 Acre Property Retreat

Waterfront Ponds, Beautiful , 51 Acre Property Retreat
Brandon
Image gallery for Reading Farms Estate

Reading Farms Estate
Reading
Image gallery for Meadow View- 35 Acres outside your door

Meadow View- 35 Acres outside your door
West Windsor
Image gallery for Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa

Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa
Killington
Image gallery for Spacious Townhouse on the Killington Access Road

Spacious Townhouse on the Killington Access Road
Killington
Image gallery for Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT

Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT
Barnard
Image gallery for Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route

Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
Ludlow
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Windsor County
You’ll often find discounted rates for long stays of over 28 days on Bookabach, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Bookabach, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Windsor County Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Bookabach with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Windsor County come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Windsor County
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Bookabach offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Windsor County with pool
Bookabach's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Windsor County
Plans change. We get that. With Bookabach, you can search, select 'free cancellation,' and see all rentals in Windsor County with flexible cancellation policies.