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Vacation rentals in Windham County

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Top-rated vacation rentals in Windham County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guesthouse in Killingly
The Carriage House at Chaprae Hall
Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.
$92 per night
Apartment in Woodstock Valley
“Tranquillity on the Lake ” Woodstock Valley, Ct.
The serenity of winter has arrived. Pretty views from your Private Apartment with walk out to lake, 1400 sq ft living space.Main suite Queen bed. Living Room Queen Sofa bed, indoor propane fireplace. Partial kitchen has stove, refrigerator,microwave & sink. Enjoy your private deck, a propane fire pit at night while gazing at the moon & stars. Outdoor grill cooking . Enjoy scenic walks around the lakes. Wake up to a beautiful sunrise. RELAX AND RENEW true LAKE LIVING
$126 per night
Apartment in Ashford
On The Run Farm
Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.
$125 per night

Other great vacation rentals in Windham County

Cottage in Killingly
Lake front cottage
$155 per night
Apartment in Mansfield
Green Energy Ecohaven
$150 per night
Treehouse in Willington
Heavenly Treehouse in Countryside w/ Farm Animals
$192 per night
Guest suite in Thompson
Meadowside: Perfect Location w/ Endless Recreation
$121 per night
Guest suite in Mansfield
Cozy private apt 8 mins from UCONN - solar powered
$66 per night
Farm stay in Woodstock
Barn suite at Southwood Alpacas
$140 per night
Farm stay in Thompson
Rustic Farmette Studio w/ Hot Tub & seasonal pool
$186 per night
Cottage in Chaplin
Clark Cottage in the historic village in Chaplin
$126 per night
Guesthouse in Hampton
Spacious, unique barn with beautiful views.
$180 per night
Farm stay in Thompson
Wizard's Roost at Underhill Hollow
$110 per night
Cabin in Windham
Secluded Cabin on Golden Pond
$122 per night
Cottage in Thompson
Private waterfront cottage on Quaddick Lake, CT
$200 per night

Destinations to explore