Vacation rentals in Windham County

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Top-rated vacation rentals in Windham County

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Guest favorite

Rental unit in Woodstock Valley

4.93 out of 5 average rating, 377 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Welcome to the scenic Northeast corner of Ct on beautiful Lake Bungee. Enjoy direct waterfront with stunning sunrises . Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars. BBQ propane grill. Stroll around both lakes . Enjoy bird sightings, nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility !!

Guest favorite

Farm stay in Thompson

4.99 out of 5 average rating, 161 reviews

Rustic Farmette Studio w/ Pool and Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Guest favorite

Guest suite in Lebanon

4.96 out of 5 average rating, 116 reviews

Relaxing, Rural one Bedroom with Private Kitchen and Bathroom at Mannamour Homestead

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard among the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark Casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Guest favorite

Guest suite in Thompson

4.99 out of 5 average rating, 143 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Guest favorite

Farm stay in Thompson

4.94 out of 5 average rating, 223 reviews

Wizard's Roost and Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

Guest favorite

Guest suite in Pomfret

4.98 out of 5 average rating, 103 reviews

Brookside Chalet

Not just a place to stay but a place where you will want to stay. - Dedicated parking space - Well-appointed full kitchen - Deck overlooking Mashamoquet Brook (our guests refer to it as the tree house:) The bed will be the highlight of your experience. This high quality queen is accessorized with a pillow top mattress, goose down and memory foam pillows and spa quality sheets and pillow cases. Location: - Five minute drive to Pomfret Prep. - Ten minute drive to main Street in Putnam.

Guest favorite

Guesthouse in Killingly

4.97 out of 5 average rating, 136 reviews

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.

Guest favorite

Farm stay in Woodstock

4.98 out of 5 average rating, 186 reviews

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Guest favorite

Rental unit in Ashford

4.96 out of 5 average rating, 164 reviews

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.

Guest favorite

Guest suite in Brooklyn

4.93 out of 5 average rating, 173 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Guest favorite

Rental unit in Ashford

4.97 out of 5 average rating, 237 reviews

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Guest favorite

Guesthouse in Hampton

4.95 out of 5 average rating, 142 reviews

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.