Ponder & Wander
12 guests
4 bedrooms
Wilmington, Windham County
Set on 22 acres of private land boasting ponds, streams and an abundance of nature – this spot in Wilmington offers a peaceful escape beyond the realms of city living. Perfect for larger groups, up to three families can stay here comfortably, with three ensuite bedrooms spread across two floors and an expansive living room on each floor - both overlooking the ponds, one with vaulted ceilings.
The Whaler's Cottage
5 guests
3 bedrooms
Sag Harbor, Southampton
Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.
Long Story Short
4 guests
2 bedrooms
Montauk, East Hampton
For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.
Explore the 932 most perfect homes in our collection
Airbnb is a shot in the dark. We meticulously vet all our homes in Massachusetts to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Massachusetts Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.
