Why Martha’s Vineyard Is a Must-Visit Before August — And Where to Stay

When you think of Martha’s Vineyard, visions of sunny beaches, pleasant walks, lobster rolls, and lively August social scenes often come to mind. But here’s a little insider secret: the magic of Martha’s Vineyard shines just as brightly — and even more peacefully — in the earlier summer months of May, June, and July.
If you’re looking for a luxurious escape without the heavy crowds (or the steep August price tags), this is your moment. Here’s why you should plan your getaway before the island’s famous August season — and how Getaway Society can make your stay unforgettable.

Why Visit Martha’s Vineyard in May, June, or July?
1. Perfect Weather Without the Overcrowding
May, June, and early July can offer beautiful weather — think highs in the mid-60s to low 80s, perfect for beach days, bike rides, and outdoor dining. The island’s famous coastal breezes keep it cool and comfortable, and you’ll enjoy all the beauty of peak summer without the August rush.
2. Better Access to Top Restaurants and Attractions
The most popular spots on the island can be difficult to access during August. In the early summer months, it’s easier to snag a table at a prime restaurant, book a last-minute boat tour, or grab front-row seating for sunset views. You’ll have the freedom to explore without feeling rushed or boxed out.
3. Lower Travel Costs and More Flexibility
Ferry tickets, flights, car rentals — everything is easier and often cheaper before the August demand spikes. Plus, our Getaway Society homes in Martha’s Vineyard are more available in May, June, and July, giving you flexibility to choose the perfect dates for your trip.

Top Things to Do on Martha’s Vineyard Before August
1. Explore Edgartown
Stroll through charming Edgartown’s historic streets lined with whaling-era homes, boutique shops, and waterfront restaurants. It’s lively but still relaxed.
2. Hit the Beaches
Early summer is ideal for beach hopping. Visit South Beach for its lively waves or Inkwell Beach for historical significance. Best of all, you’ll enjoy plenty of space to spread out your towel.
3. Visit Oak Bluffs
Oak Bluffs is home to the colorful Gingerbread Cottages and one of the oldest operating carousels in the U.S., the Flying Horses Carousel. Grab a coffee at Mocha Mott’s, dinner at The Wharf, and make sure to pick up the famous apple fritters at Backdoor Donuts.
4. Bike or Hike the Island
The early summer weather makes biking a dream. Rent a bike and cruise along the scenic trails from Vineyard Haven to Edgartown — or hike the Menemsha Hills Reservation for sweeping ocean views.
5. Enjoy Fresh Seafood and Farm Stands
Island chefs celebrate local ingredients all summer long. Visit the Menemsha Fish Market for the freshest lobster roll of your life or pick up fresh berries and farm-grown produce at Morning Glory Farm.
6. Lighthouse Tours and Scenic Views
May through July is the perfect time to visit Martha’s Vineyard’s iconic lighthouses without the heavy foot traffic. Don’t miss the stunning Gay Head Lighthouse and Aquinnah Cliffs.
7. Hit the Water
Book a kayak or stand-up paddleboard rental, or take a sailing tour of the island’s beautiful coastline. With smaller crowds, you’ll have more flexibility to pick times that work best for your group.
Stay in Style with Getaway Society
Whether you’re planning a romantic escape, a family vacation, or a friends’ retreat, Getaway Society’s luxury homes on Martha’s Vineyard are your ideal home base. Our properties offer spacious layouts, beautiful décor, and prime access to the island’s best attractions.
Skip the August frenzy. Discover the Vineyard’s softer side in May, June, or July — when the ocean breeze is just as sweet, and the island feels a little more like your own private escape.
Ready to experience Martha’s Vineyard like a true insider?