Holiday rentals in Windham County

Country Lake Oasis

Escape to tranquility at this waterfront retreat! Breathtaking sunset views over a pristine, swimmable lake with a sandy beach and floating dock. Newly updated home features a relaxing spacious deck, fully equipped kitchen and pristine wood floors. Nestled on a quiet dead-end street, this haven offers a kayak and paddle boat for water adventures. Embrace the serenity with an outdoor fire pit, fishing from the pier, and lakeside BBQs. Inside, discover an Experience rural beauty. Paradise awaits!

Woodpecker’s Nest

With 15 acres of private wooded land, count on High Speed Wi-Fi throughout the Woodpecker's Nest if you work from home or just need to catch up on emails! Coffee bar is stocked, have a cup taking in an ideal view of the woods! Television is ready to stream movies with family & friends! Plenty of indoor & outdoor seating for meals as you watch the sunrise or sunset cast pink hues over the woods & sky! As the sky darkens & the stars light up, gaze up in wonder in a very quiet area of New England!

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!

Antique Home w Private Pond, Sturbridge /Brimfield

Minutes to Sturbridge, great craft breweries, (including TreeHouse), Brimfield Antique Flea Market. Our recently ( and ongoing) renovated 1800s farm house is ready for your next stay. It is quirky and not for perfectionists! Visit nearby Old Sturbridge and its many great shops and restaurants, and nearby State Parks. Plenty of room, fully equipped kitchen, comfy living rm & big dining room. 3 comfortable bedrooms upstairs. Very easy off/on the highway to be on your way quickly!

3-bedroom cottage in serene Lake Bunggee area

Discover the vibrant Lake Bunggee community in Woodstock Valley, CT, reminiscent of a sprawling campground. Relax into CT’s Quiet Corner within our rustic retreat. Enjoy leisurely lakeside walks, and two complimentary kayaks for your adventure. Just 10 miles away you'll find Putnam, known for its charming antiques and restaurants. Only 18 miles from the famous Brimfield Flea Markets, 16 miles from Old Sturbridge Village, and within reach of Worcester, Hartford, NYC, and Boston.

Calm & Cozy House in a Quiet Corner

The perfect place to get away to enjoy a Best Kept Secret of New England. You will have access to the whole house during your stay. All on one level (ground floor). Enjoy the relaxing view of the field, red barn and Quinnebaug River while snuggling up with read a book. The country kitchen is complete with refrigerator, toaster, oven, microwave, and coffee maker. The best of Putnam Antique District, Entertainment, Dining, Nightlife and shopping a 4 minute drive away.

House on Little River / Writer Retreat

Rustic cottage on on Little River, a lovely trout stream that swishes around rocks. Great place for kids to play! Lake across the street. Canoe. Woods all around. Very quiet except for hush of river. Nice deck extends almost to the river. Charcoal grill. In all ways cozy and pleasant. Nice for couples, writers, artists, travelers, families, and pets—a place for quiet, peaceful people. About the lake: There's no beach. Access is just a narrow path down to the water.

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.

Secluded 2 Acre Lake Front Home!

Escape to this breathtaking retreat on Lake Chamberlain, tucked away in Connecticut's serene "Quiet Corner". This spacious 2-acre home offers total privacy and stunning natural beauty. In the summer, dive into swimming, fishing, and kayaking 🛶🏊‍♀️. When winter arrives, experience ice skating ⛸️ right on the lake! Whether you're here for relaxation or adventure, this peaceful getaway will steal your heart. Once you arrive, you may never want to leave! 🏡💖