Luxury Walking Holidays in Massachusetts

Discover the best of Nantucket villas in this exquisite waterfront beach home with tennis court, pool and gym. Book this villa to enjoy the best of Nantucket vacations for getaways with friends and family. The waterfront home has a private walkway to your own beach, private tennis court, [...]

The Harborside Inn has been welcoming visitors to the beautiful island of Martha’s Vineyard for over 50 years. The only waterfront hotel in Edgartown, The Harborside Inn is a great place for couples looking for a romantic getaway, or families looking for a location with easy access to the [...]

With harbor views, this Brant Point villa is perfect for beach vacations. Sharing beach access to Hulbert Avenue beaches and a tennis court, the private vacation rental is furnished with tasteful antiques and modern amenities. The classic New England home features a widow's walk with 360-degree [...]

This one-of-a-kind Nantucket beach home has a pool, private tennis court, hot tub, outdoor shower, viewing deck of the ocean, lush flower gardens and the quintessential classic Nantucket ambiance. Relax in this picture-perfect beachfront villa overlooking the ocean and soak up the best of [...]

This Martha's Vineyard home is a quiet hideaway that accommodates up to 7 guests in 4 bedrooms. You'll feel absolute delight when you enter this exquisite custom home on an acre of land in a private area, but within close walking distance to downtown. The vacation home is bright & summery, two [...]

This 3 Bedroom villa sleeps 6 with area of 2900 sq.ft and has 3 Bathrooms. The lovely home on Martha's Vineyard has a fireplace, outdoor grill, and beach chairs for guests' enjoyment. It's a great vacation site - the beach is three miles away and golf and fine dining are within eight [...]