Best Budget-Friendly Lodging: 

(TIE)

Ashley Inn 

129 Main Street, Edgartown, 508-627-9655, ashleyinn.net

Martha’s Vineyard Family Campground

569 Edgartown–Vineyard Haven Road, Vineyard Haven, 508-693-3772, campmv.com

Runner-up: Edgartown Commons

20 Peases Point Way North, Edgartown, 508-627-4671, edgartowncommons.com

This year’s budget-friendly tie-holders offer varying experiences at affordable prices. At the Ashley Inn guests can enjoy Georgian elegance inside a nineteenth-century sea captain’s home, while the Martha’s Vineyard Family Campground offers a woodsy setting with DIY spirit. Edgartown Commons features apartment-style lodging with a pool and playground on-site. 

Best Family-Friendly Lodging: Harbor View Hotel

131 North Water Street, Edgartown, 844-248-1167, harborviewhotel.com

Runner-up: Winnetu Oceanside Resort

31 Dunes Road, Edgartown, 508-310-1733, winnetu.com

Children on vacation can never get enough of the water; that’s why the Harbor View Hotel – with its heated, saltwater pool – is a great solution for families. The Winnetu Oceanside Resort makes families happy with s’mores, a pirate ship playground, and pool. Both spots are within walking distance of the beach.

Best Hotel, General Excellence: Harbor View Hotel

131 North Water Street, Edgartown, 844-248-1167, harborviewhotel.com

Runner-up: The Charlotte Inn

27 South Summer Street, Edgartown, 508-627-4751, thecharlotteinn.com

What qualities make the Harbor View Hotel a favorite year after year? A wraparound porch overlooking Edgartown’s lighthouse and harbor, plentiful fine dining options, and poolside cabanas, to name just a few. A few blocks away, you can step back in time at the Charlotte Inn, a well-appointed luxury inn.  

Best Romantic Getaway: The Charlotte Inn

27 South Summer Street, Edgartown, 508-627-4751, thecharlotteinn.com

Runner-up: Harbor View Hotel

131 North Water Street, Edgartown, 844-248-1167, harborviewhotel.com

Privacy and personal service prevail at the historic Charlotte Inn, which is conveniently located a block from Edgartown’s Main Street. Standout features include exquisite artwork and decoration, plus a top-notch staff. The Harbor View Hotel’s waterfront location offers sweeping views.