Find Winchester motels

If you’re having trouble locating a motel in Winchester, let us help you find a motel or similar property from over 360 accommodations in the larger area. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free parking and free airport transportation.

Motels often have free parking, and many also feature an outdoor pool. Often one or two stories tall, motels usually have exterior corridors overlooking the parking lot or an outdoor pool. In the U.S., motels became more commonplace after World War II with the popularity of car travel and road trips, peaking in the 1960s with over 60,000 properties.

Here you’ll find some of our customers’ top motels in the larger area. Colonial Motel And Spa is located 11.5 mi (18.5 km) from the heart of Winchester. Enjoy access to the 2 indoor pools, and freebies including WiFi and parking. The Putney Inn: A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Central Winchester is 14.9 mi (23.9 km) away. Econo Lodge Brattleboro: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi, and parking. Located 10.3 mi (16.5 km) from the heart of Winchester. Travelodge by Wyndham Brattleboro VT: Central Winchester is 11.8 mi (19 km) away. Free WiFi, free parking, and a 24-hour front desk are available during your stay.

Those who’ve visited Winchester like the lakeside. As you’re sightseeing around the area, be sure to enjoy all there is to see and do. These are some of the parks and outdoorsy places: Birch Point, Pisgah State Park, and Rhododendron State Park. You’ll find these family-friendly sights in the area: Brattleboro Bowl, Friendly Farm, and Northern Illusion. While you’re checking out the area, consider visiting Ashuelot River, Moody Center, and Northfield Mount Hermon School.

Weather can make or break a roadtrip, so here’s some data about year-round temperatures in Winchester to help you plan yours: The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, April, and February, with each month seeing an average of 11 inches of snowfall.