Winchester Holiday Rentals
Holiday Rentals in Winchester
Charming Waterfront Log Cabin
Cozy Cottage Along Idyllic Green River
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Hilltop Home with Great Views
Waterfront Cottage on Scenic Sportsman Pond
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Lakefront Orange Vacation Rental - Pet Friendly!
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
A vacation destination in Southern Vermont
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Spectacular Mountain views with all the amentities nearby
Other types of properties in Winchester you may be interested in
Colonial Motel And Spa
The Colonial Hotel
The Covered Bridge Inn
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.
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