Massachusetts is a haven for travelers seeking both relaxation and adventure. From the iconic island of Martha’s Vineyard to the historic towns of Cape Cod, you’ll find something to suit every taste. Whether you’re eager to explore New England’s coastal charm, take in the natural beauty of the region, or discover Massachusetts' rich cultural and historical heritage, our luxury vacation rentals are ideally situated to help you experience it all.

After a day of exploring, return to your private sanctuary — a peaceful retreat where you can unwind in elegance and comfort. Our properties in Massachusetts offer luxurious features like outdoor patios, pools, and gourmet kitchens that allow you to fully embrace the laid-back, luxurious lifestyle of New England.

Massachusetts Weather: When Should You Visit?

Massachusetts is a year-round destination, with each season offering something unique:

• Spring: As the state awakens from winter, spring brings mild weather and blossoming landscapes. This is the perfect time for outdoor activities, like hiking and visiting local farms.
• Summer: Summer in Massachusetts means warm days, cool ocean breezes, and plenty of time for beach outings, sailing, and exploring coastal towns.
• Fall: Fall is an especially magical time to visit Massachusetts. With its famous fall foliage, crisp air, and numerous harvest festivals, it’s the ideal time for scenic drives, apple picking, and leaf-peeping.
• Winter: For a cozy winter getaway, Massachusetts offers quiet, snow-covered landscapes, perfect for fireside evenings in one of our luxurious homes. Winter sports enthusiasts can also find skiing and snowboarding opportunities in nearby areas.

Food and Drink in Massachusetts

Massachusetts has a thriving food scene, rich in fresh seafood and farm-to-table dining experiences. From casual clam shacks serving the best lobster rolls to upscale dining options featuring locally sourced ingredients, the culinary landscape here is vibrant and diverse.

Start your day with a visit to a local café, where you can indulge in freshly baked pastries and expertly brewed coffee. For lunch or dinner, enjoy a seafood feast at a waterfront restaurant, sampling oysters, scallops, and the freshest catch of the day.

If you’re staying with us at Wander Martha's Vineyard, discover the best restaurants in Martha’s Vineyard.

Points of Interest in Massachusetts

Massachusetts is rich in cultural landmarks and natural beauty, offering plenty of attractions for visitors of all ages:

• Martha’s Vineyard: This iconic island is the ultimate summer destination, known for its scenic beaches, charming towns, and luxurious retreats. Spend your days exploring the lighthouses, vineyards, and local boutiques that give the island its unique character.
• Cape Cod: Famous for its quaint seaside villages, Cape Cod is a must-visit for those seeking a classic New England beach vacation. Enjoy whale watching, biking along the Cape Cod Rail Trail, or simply lounging on one of the many pristine beaches.
• Boston: If you’re interested in history and culture, a day trip to Boston offers a wealth of opportunities. Visit historic landmarks like the Freedom Trail, Fenway Park, or the Museum of Fine Arts, before returning to the tranquility of your vacation rental.
• Nantucket: Another luxurious island getaway, Nantucket is known for its cobblestone streets, high-end boutiques, and stunning beaches. It’s a perfect day trip from Martha’s Vineyard if you want to explore more of Massachusetts’ coastal beauty.

Incredible Activities in and Around Massachusetts

Our luxury vacation rentals in Massachusetts put you in the perfect spot to enjoy the best activities the state has to offer. Whether you’re an outdoor enthusiast or a culture lover, there’s something for everyone.

• Outdoor Adventures: Massachusetts’ varied landscapes are perfect for hiking, biking, and water sports. Spend your days kayaking in coastal waters, hiking in state parks, or sailing off the coast of Cape Cod or Martha’s Vineyard.
• Cultural Experiences: For those who appreciate the arts and history, Massachusetts is home to world-class museums, galleries, and historical sites. Explore the rich maritime history of the region or attend one of the many arts festivals that take place throughout the year.
• Festivals and Events: Depending on when you visit, you might be able to catch one of the state’s famous festivals, like the Nantucket Film Festival or Martha’s Vineyard Food & Wine Festival.
• Relaxation and Leisure: If you’re looking for relaxation, spend your days lounging by the pool at your rental, taking in the stunning scenery, or enjoying a spa day at one of the nearby luxury resorts.

Read our full guide to the best activities in Massachusetts for more inspiration for your vacation.

Choosing Where to Stay in Massachusetts

Wander offers exceptional properties in Massachusetts, each tailored to provide a unique and luxurious experience for your stay.

Wander Martha’s Vineyard in Edgartown

Wander Martha’s Vineyard is a secluded island retreat that embodies coastal luxury. Nestled on 1.6 gated acres, this home offers four bedrooms, three baths, and a host of high-end amenities. Whether you’re taking a dip in the gunite saltwater pool, relaxing by the fire pit, or enjoying a game of bocce on the lawn, this property provides the ultimate blend of privacy and luxury.

With its fully equipped gym and expansive outdoor spaces, Wander Martha’s Vineyard ensures a perfect balance between relaxation and adventure.

Getting Around

Massachusetts is well connected, making it easy to explore its many attractions. Logan International Airport in Boston offers flights from all over the country, and ferries to Martha’s Vineyard and Nantucket provide convenient access to the islands. If you’re traveling to our Martha’s Island property, read our helpful Wander Martha Vineyard’s transportation guide to get you to and from your destination seamlessly.

Renting a car is recommended for flexibility, especially if you want to explore more remote areas and hidden gems. Our luxury vacation rentals are located near key points of interest, ensuring that you’re never too far from the best that Massachusetts has to offer.