Private suite holiday rentals in Windham County

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Top-rated Self-Contained Units in Windham County

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Guest suite in Newfane

4.82 out of 5 average rating, 17 reviews

The Newfane Loft - Cozy Retreat in Vermont Village

Tucked away in a cozy Vermont village, the Newfane Loft is a perfect blend of rural pastoral getaway and accessible convenience. Park the car, step out onto the patio, and let your senses take in the smell of the air, the towering sycamore, and trickling brook behind the house. The living space features large skylights, a sleeping nook with a comfortable queen-sized bed, and a kitchen to prepare your farmer’s market haul. An ideal base for everything from skiing & hiking to antiquing & crafts.

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Guest suite in Westminster

4.96 out of 5 average rating, 54 reviews

COZY FARMHOUSE SUITE

Take it easy at this unique and tranquil getaway nestled in a revolutionary historically significant village. You can experience farm living while still close to Rte 91, an Amtrak station and the Connecticut river for fun water activities. This recently renovated studio has a private entrance with parking right outside. Fully equipped kitchen. Bathroom with tiled shower stall, easily accessible. The beautiful sleeping nook is perfect for two. Adorable sitting and dining/work areas.

Guest favourite

Guest suite in Putney

4.95 out of 5 average rating, 64 reviews

Peaceful Country Retreat on 15 Secluded Acres

Quiet and pristine guest suite, nature lover’s paradise. This is a private home on 15 acres . Hiking trails nearby. A 7 minute drive to downtown Putney, 20 minutes to Brattleboro and 50 minutes to mount snow ski resort. Fall foliage and apple picking or summer hiking and blueberries, farmers markets and swimming holes. Local entertainment venues include Next Stage performing arts, Yellow Barn and Putney is home to the Sandglass Theatre 🎭 Come experience Vermont: rest and rejuvenat

Guest favourite

Guest suite in Chester

4.89 out of 5 average rating, 63 reviews

Adorable, Cozy 2 bedroom apartment walk to village

Welcome to this cute and cozy self-contained unit with all the amenities you could need! Walk to Chester VT Village green, just 14.2 miles from Okemo! A beautiful space, you have the entire apartment to yourself - 2 bedrooms with queen sized beds, a cozy living room and a kitchenette that provides everything you need for your stay! Washer/dryer, parking out front and even a deck off the back to enjoy in the warmer months! This is a great place for a getaway OR a longer stay!

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Guest suite in Brattleboro

4.94 out of 5 average rating, 572 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

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Guest suite in Wilmington

4.92 out of 5 average rating, 768 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

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Guest suite in Putney

5 out of 5 average rating, 48 reviews

Lovely Studio in Putney

This charming, newly constructed private studio retreat in beautiful Putney, Vermont is an idyllic base for a romantic weekend getaway, a solitary writing retreat, or just some quiet time to recharge your batteries. Adjacent to a painting studio with its own driveway/parking area, this self-contained little casita in the dappled shade at the edge of a forest meadow comes with a queen bed, reliable internet, shower and bathtub, and kitchenette.

Guest favourite

Guest suite in Putney

4.94 out of 5 average rating, 50 reviews

Southern Vermont getaway

Spacious, comfortable and very large light-filled one bedroom all to yourselves. The single-story unit is attached to our lovely farmhouse but has a separate entrance. Hardwood floors, exposed beams and beautiful views of gardens and woods for a one-of a-kind retreat in beautiful Putney, VT. Close to skiing, hiking, and kayaking (45 min to Mt Snow, Okemo, Grafton ponds and more). Plenty of room for reading, TV, cooking, working or napping.

Guest suite in Dummerston

5 out of 5 average rating, 11 reviews

Paradise by the Brook Studio Space

Though in the woods where quiet and soothing sounds of nature abound, you are just ten minutes from downtown Brattleboro. Skiing , maple sugaring, kayaking, many nearby swimming holes, restaurants, shops and galleries galore all a short car ride away. This is a beautiful, off the grid, rustic home. The simple life, here by the brook, can be a profound experience of transformation very different from a stay in a luxury resort hotel. I

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Guest suite in Newfane

4.93 out of 5 average rating, 206 reviews

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Starlink wifi.

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Guest suite in Jamaica

4.78 out of 5 average rating, 144 reviews

Renovated Apartment by Mount Snow & Stratton

Stunning property in the countryside. Nature lovers paradise with two ponds on the property that guests can fish, as well as a beautiful swimming hole located at the bottom of the property with a sandy beach. Conveniently located in between Mt. Snow, Stratton and Bromley Mountains. Close to Jamaica State Park, Townshend Damn and Manchester is 30 minutes away. There is a new hot tub and fire pit located in the backyard

Guest favourite

Guest suite in Newfane

4.9 out of 5 average rating, 348 reviews

Cozy Apartment

We love our home on a dead end dirt road, quiet and private, yet close to all you need and want when you think of VT. Ski (Mt. Snow or Stratton), hike, swim, enjoy local fare at great restaurants or shop the Brattleboro Farmer's Market or food coop. Enjoy a swim at the covered bridge in Dummerston or at the convergence of the Rock and the West Rivers. Or drive up Newfane Hill to Kinney Pond.