Plan your trip
Photo by William Keller
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Check prices for these dates, December 14 – 15, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breakfast included
Hot tub
Spa
4 stars
5 stars
Oak Bluffs is a delightful coastal escape filled with unique attractions and activities that cater to adventurous travelers. Begin your journey with a stroll through the vibrant streets of the town, where you can marvel at the iconic gingerbread cottages, each one a colorful work of art that narrates the rich history of summer vacations on Martha's Vineyard. For a taste of local culture, visit the lively Oak Bluffs Harbor, where the picturesque views of the marina create the perfect backdrop for a leisurely afternoon—enjoy fresh seafood from nearby eateries or simply soak in the ambiance. Don't miss out on the serene experience of a sunset at the beach; the gentle waves and soft sandy shores provide a perfect setting for relaxation and reflection. For families, the nearby scenic bicycle paths offer a fun way to explore the area together, allowing you to enjoy the beauty of the landscape at your own pace. Finally, immerse yourself in the local arts scene by visiting the numerous galleries and studios, where you can discover handmade crafts and artwork that showcase the island's creative spirit. With such a variety of experiences, you’ll find that staying in Oak Bluffs puts you right at the heart of this enchanting destination.
Summercamp: Resort located near Inkwell Beach. Offers 3 outdoor tennis courts, a seasonal outdoor pool, and free self parking. MV Surfside Hotel: Vacation home located near Inkwell Beach. Features sun loungers, a pool, and kitchens. Morgan Hotel: Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Pequot Hotel: Offers a snack bar/deli, an indoor pool, and free self parking. The Island Inn on Martha's Vineyard: Provides complimentary wireless internet access, an indoor pool, and televisions.
Surround yourself with nature at Ocean Park and Oak Bluffs Town Beach. During your stay, check out sights such as Circuit Avenue, Flying Horses Carousel, and Oak Bluffs Harbor. The beaches, wineries, and shopping are just some of the things to enjoy while you're in the area.
Taking into account the local weather in Oak Bluffs is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.