After nearly 20 years living in the south, my high school roommate Rhiannon is (finally!) moving back to New England. To celebrate, all my high school friends are planning one of our signature late-fall New England getaways. Though we haven’t settled on a destination yet, here’s where we’ve been in years past that were always a hit if you’re looking for cozy autumn vibes, apple picking, scenic views, foliage, and winter wonderlands.
Sutton, Quebec

Last December, three of us rented this Mansonville QC Airbnb for the weekend and felt like we were in a snowglobe. Knowing next to nothing about the area, we were happily surprised to find the village of Mansonville to have a cute downtown with a coffee shop, French bakery and a specialty Italian shop selling the most insane homemade focaccia. It’s also a short drive to the ski town of Sutton, QC where a visit to Microbrasserie a L’Abordage is a must for poutine & beer. Right over the US border is Golden Dog Farm (where you can frolic with a dozen Golden Retrievers), and the Vermont ski resorts of Stowe and Jay Peak.
Putney, Vermont

This bungalow in Putney, VT was my very first Airbnb booking back in 2014, and while a completely random town choice, it ended up being chock full of everything you’d need/want – an adorable food coop, a BBQ joint run out of an old school bus, a winery/distillery, and several really nice restaurants.
Woodstock, Vermont


Home to dozens of covered bridges, Woodstock is a classic Vermont town with tons of cozy bars & restaurants. The Woodstock Inn is a stately spot in the center of town right on the common/green, the town of Quechee is nearby (home to the Simon Pearce restaurant on the river with live glass-blowing in the basement), and it’s only a short drive to the Harpoon Brewery and White River Junction, home to Big Fatty’s BBQ and River Roost Brewery.
Meredith, New Hampshire

Located in the Lakes Region of New Hampshire, Meredith is one of the nicer towns in the state. And yes, that is shade to New Hampshire, my least favorite of the New England states. Meredith is a nice home base to have an al fresco wine & cheese at the Hermit Woods Winery, walk the live animal exhibit trail at Squam Lakes Natural Science Center in Holderness to see rehabbed foxes, owls, coyotes, bobcats and mountain lions, and have beers & buffalo chicken dip at Twin Barns Brewery.
Waterford, Maine


With our home base as this log cabin in Waterford, ME, we went apple-picking at Pietree Orchard in Sweden, Maine, drove along the Maine-New Hampshire border for foliage vibes, and had a killer breakfast at Beth’s Kitchen Cafe in Bridgton.
Cozy Cabins for Winter Airbnb Wishlist
From geodesic domes to full-on mountain lodges, this exhaustive Airbnb wishlist covers all the bases all over New England.