For most families, a full-service resort on Martha’s Vineyard is the better choice for a short, hands-off trip, while a VRBO rental wins out for longer stays or bigger groups who want their own kitchen and space. Both can work beautifully for a lazy family trip. It comes down to how much you want handled for you versus how much space you need. By the end of this comparison you’ll know which option fits your trip length, group size, and budget.
At a Glance: Resort vs. VRBO
| Accommodation Type | Best For | Pros | Cons | Booking Options |
|---|---|---|---|---|
| Full-Service Family Resorts | Parents who want zero cooking or cleaning | Pools, kids’ programming, daily housekeeping, on-site dining | Higher nightly rate, less room to spread out | Compare Rates → |
| Private VRBO Rentals | Larger families and longer stays | Full kitchen, laundry, separate bedrooms for naps | You’re on your own for meals and cleanup | Compare Rates → |
Option A: Full-Service Family Resorts
The Winnetu Oceanside Resort in Edgartown is the easiest resort stay on the island, with a dedicated children’s program and suites big enough for three generations.
It is relaxed and built around families, with organized activities that keep kids busy while parents get a break. The heated outdoor pool has a shallow end for younger swimmers. Book a suite rather than a standard room, because the extra space matters when there is a travel crib involved. It is a premium property on a popular island, so reserve as soon as you know your dates. The best weeks sell out early.
For a more historic, walkable base, the Harbor View Hotel in Edgartown puts you within strolling distance of shops and ice cream stops, with an outdoor pool overlooking the Edgartown Lighthouse.
It feels polished but is still easygoing about strollers and sandy feet, and the outdoor pool looks out at the lighthouse. Skip the rental car if you stay here, since the shops and restaurants on this stretch of Edgartown are all within walking distance. The central location gets busy in peak summer weeks, so book dinner reservations early as well.
Option B: Private VRBO Vacation Rentals
A private home solves the two things a resort cannot, a real kitchen and a door you can close at nap time. For stays of five nights or more, or trips with grandparents, a VRBO usually wins on space and on total cost. You can cook half your meals instead of paying resort restaurant prices, and everyone gets a room instead of sharing a suite.
The Verdict: Which Should You Book?
Book a resort like the Winnetu Oceanside Resort or the Harbor View Hotel if you want someone else handling the towels, breakfast and entertainment. That is the easier choice for a short trip or a first visit. Book a VRBO if you are traveling with more than one family, staying a week or longer, or want your own kitchen and schedule. Either way, leave the days on either side of the ferry unplanned.
FAQs About Staying in Martha’s Vineyard
Is Martha’s Vineyard expensive for families? Yes, especially in peak summer. A trip in late spring or early fall can cost much less for lodging and still have good weather.
Do I need a car on Martha’s Vineyard? Not if you stay in Edgartown or Oak Bluffs. Both are walkable and linked by a seasonal shuttle bus. A car helps if you are staying farther out or want to see Aquinnah.
How far in advance should I book?
For summer travel, book resorts and VRBOs 4-6 months ahead. The island’s inventory is limited and the best family-friendly options go first.
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