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Winchester flight + hotel packages

Mountain Lodge at Okemo

Jackson Gore Village

Solitude Village at Okemo

Okemo Mountain Lodging

Mount Snow Grand Summit Resort
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The Colonial Hotel

Best Western Plus Keene Hotel

Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

The Putney Inn

Courtyard by Marriott Keene Downtown
Popular places to visit
New England Sweetwater Farm & Distillery
You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
Loring Field
Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.
Richmond Town Hall
After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.
Winchester Vacations
Get your vacation off to an amazing start by learning a bit about Winchester before you head off.
You'll find this town 10 miles (16 kilometers) from Brattleboro and 12 miles (19 kilometers) away from Keene.
Forget the big-name attractions — it's the locals that make a place tick. In this part of New Hampshire, you'll find 2,000 of them.
Places to visit in Winchester
Bridges are often iconic local symbols. Stop at Schell Bridge and learn when and how it was built and the part its played throughout history. Still need some more options? Of all the roads you take in life, make sure some of them are dirt! So slip into those boots, fill up your water bottle and tackle the hikes of Metacomet-Monadnock Trail.Where do you fly into for Winchester?
There's nothing like the feeling of finally touching down in a new, unknown destination. If you're heading to Winchester, there's a good chance you'll fly into Manchester-Boston Regional Airport (MHT). It's about 50 miles (80 kilometers) to the east of the downtown area. Collect your belongings and get set to kick-start your vacation!Photos of local treasures
Browse Winchester vacation photos for more inspiration