Vacation rentals in Winchester

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

Stone n' Sky Lodge

Complete with all the comforts & amenities of home, Stone n’ Sky Lodge is fully furnished & decorated with family heirlooms & fine art. Featuring a fully equipped kitchen, fiber optic internet & a separate home office, the Lodge is located on a paved, dead end road, surrounded by a wildlife sanctuary; yet minutes from town & interstate highways. Local attractions, festivals, artisans, hiking, micro-brewed beers, ciders, good food & music are all to be discovered within minutes of this location.

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Discover the ultimate outdoor experience in Southern NH! Enjoy a year-round private hot tub in a covered gazebo, fire pit, hammock, life-size games, and swing set. Located in one of Keene’s safest, quietest neighborhoods, walking distance to downtown and across from Keene Ice Rink. Close to beaches, hiking, and ski resorts. Features a fully stocked chef’s kitchen, wine cooler, and luxury Purple mattresses with individual mini-splits in each bedroom for optimal comfort.

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Charming Country Home

Charming one level ranch style home. Quiet country neighborhood 5 miles from Keene, NH, 10 miles from Brattleboro, VT. The home has a fully equipped kitchen, smart TVs, spacious rooms, two bedrooms, two full baths, laundry in basement, couple of steps to master bedroom. Great backyard. Spacious driveway with motion lights.