Our mission is to serve the 50+ traveler. We want to inspire you to explore new destinations, discover new experiences, and savor the journey.
Martha’s Vineyard is an island in the Atlantic Ocean — just south of Cape Cod — part of the state of Massachusetts. Known for its many gorgeous beaches, Martha’s Vineyard is a very popular summer destination that also happens to have quite a few cottages available for rent. We’ve pulled together a few of the best cottages for you to help you plan your trip.
With lots to choose from, we’ve made sure that this list has only highly-rated options, most of which feature many, many good reviews. As you might have guessed, based on the “cottage” headline, nearly all of these are cozy with space for just two to four people. All of them, though, are sure to please!
Before you head out on vacation, you might take a few moments to learn a little about your destination, including some tips on how to best enjoy your time on this beautiful island. You might also find yourself wanting to become more familiar with the area in general, as there are a lot of things to do not just in Martha’s Vineyard, but also in Cape Cod and other surrounding areas. Overall, this is a great area with so much to offer. Book your stay soon!
Casa Chica is a guest house cottage that is sure to impress! Just 5 minutes to downtown Edgartown, you’ll also be close to a bike path, public transportation, Sengekontacket Pond, and so much more. Renovated and nestled in a charming and beautiful spot, Casa Chica is on a quiet dirt road, offering the chance to enjoy nature; a perfect spot for couples. The kitchen comes with a gas stove, microwave, and coffee maker. Outside, you’ve got an outdoor shower, seating, and a gas grill. Downstairs, you’ll find a washer and dryer along with beach chairs for your use.
Quiet, quaint, and comfortable, you will not regret checking out this contemporary cottage on a private, wooded lot. This beauty is a must-see, pristine, bright, and comfortable furnished with an open-living area, hardwood floors, vaulted ceilings, indoor and outdoor fireplaces, a well-appointed kitchen, a washer and dryer, and more! You can walk or bike to beaches, trails, or the West Chop Lighthouse. You can also drive just 5 minutes to downtown shops and restaurants. This is yet another extremely appealing option with lots of curb appeal!
Greetings from Idle Hour Cottage, a stylish Edgartown option situated between downtown and South Beach. It’s just a 5-minute walk to the Katama General Store and it’s located right on the bike path. Bright and inviting, Idle Hour Cottage has vaulted ceilings, plank floors, luxury finishes, and lots more amenities on a gorgeous 1-acre lot. Inside, you’ll love the mix of new and vintage furniture in the sitting room, the fully-equipped kitchen, and the queen bedroom. Outside, relax on the outdoor deck that has a dining set, chaise lounge seating, and an umbrella. Feel free to take advantage of the provided sand chairs, beach bag, cooler, beach towels, and spa robes!
If lots of privacy is something you seek, this quaint little cottage located in the heart of East Chop is for you! East Chop Lighthouse is short walking distance away, and the public beach is just a half-mile away. This cottage has a kitchenette with a full-sized fridge, but please note: the stove is antique and not in service. Only an outdoor (but well-equipped) shower is available! Quirky and fun, be sure to check this one out. Internet and reception is spotty in the area. The host advises that if you need a strong internet connection, you might look elsewhere. This space is not suitable for bringing children.
This one is definitely the exception to the “small” option noted above, a four-bedroom with space for up to eight guests! Wild Child Writer’s Cottage has three first floor bedrooms and a fourth bedroom in the loft, not to mention a hot tub, outdoor shower, and wonderful kitchen. Nestled in the woods just steps from miles of trails, you can walk to the beach, wander through the woods of Long Point Wildlife Refuge, or just relax! The photos just ooze privacy — the perfect spot for your getaway.
What a location! This quiet, charming beach house cottage is located right on the beach, the perfect spot for a relaxing visit to Martha’s Vineyard and to enjoy gorgeous sunsets. A couple’s retreat (no extra guests allowed), you are going to love the view of Lagoon Pond and the full kitchen. Or you can head outside to the firepit area, which is shared but accessible to you!
The Sweet Island Cottage is a 500-square-foot pet-friendly guest cottage on a peaceful, residential hilltop with an open kitchen and living area walkable to parks, the beach, and downtown. Relax outside with a fenced yard, barbecue, and brand new fire pit! Located on the outskirts of the historic town of Vineyard Haven, this cottage is charming and tastefully decorated — perfect for your getaway. Just a 7-minute walk to the Lagoon and boat rentals, a mile to Owen Little Park Beach, or just a 3-minute walk to the Martha’s Vineyard Museum! This is a great space inside and out. Be sure to give it a look.
Interested in a brand new single-family vacation home? Look no further! Modern and newly constructed in 2021, this Martha’s Vineyard Airbnb is bright, comes with high-vaulted ceilings, laundry in the unit, a full kitchen with quartz countertops, and lots more. It also includes a king-sized bed and queen pull-out couch. Enjoy the patio area with an outdoor shower and gas grill. Right next door you’ll find a local market and deli, and great barbecue right across the road. With easy access to Oak Bluffs boats and public transportation, this one is incredible!
Newly built and spotless, this 500-square-foot cottage comes with a full kitchen, granite countertops, new appliances, a Keurig, and more! Step out to the beautifully-landscaped stone patio with a large gas grill and outdoor shower for rinsing off after hitting the beach. You’ll be just a 5-minute walk from downtown Oak Bluffs, the beaches, and right next door to a local market and deli. This entire cottage is your space, with laundry in the unit. Check this one out soon.
To discover even more things to do in and around Martha’s Vineyard, check out: