Best Budget-Friendly Lodging: Edgartown Commons

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

Runner-up: Martha’s Vineyard Family Campground

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

Looking for affordable prices and the convenience of staying downtown? Look no further than Edgartown Commons. The apartment-style lodging features kitchens, on-site laundry, and a playground. Adventurers can enjoy the great outdoors and a community of fellow travelers at the Martha’s Vineyard Family Campground, which rents sites for RVs and tents.

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, 508-627-4747,  winnetu.com

At frequent winner Harbor View Hotel, families can splash in the on-site pool, ride complimentary bikes into town, or walk to the nearby Edgartown Lighthouse and beach. Winnetu Oceanside Resort has a giant chessboard, a vintage fire truck, and the waves of South Beach just a short stroll away.

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 makes the Harbor View Hotel generally excellent? A wide porch with views of the lighthouse and outer harbor, a fine dining restaurant, private cabana rentals at the pool…the list goes on. The Charlotte Inn is an esteemed, one-of-a-kind property with a high-end restaurant and an impressive art collection.

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

A trip to the Charlotte Inn feels like time-traveling. The award-winning hotel is known for its exquisite, period-accurate nineteenth-century furnishings and décor, making it the ideal spot for a tranquil Island retreat. Overlooking Edgartown Lighthouse, the Harbor View Hotel is perfectly located for a short walk to the beach or downtown.