What sets the weekly rate
- Town and setting. Edgartown in-town homes, waterfront Chilmark and Aquinnah sunsets, and walk-to-town Oak Bluffs each have their own market.
- Bedrooms and sleeping space. The number of people a home sleeps comfortably matters more than square footage.
- Water. Waterfront, water views and private beach access carry the biggest premiums on the island.
- Walk to town or beach. Guests pay for leaving the car in the driveway.
- The extras guests search for: a pool, central air, an outdoor shower, a great kitchen, a deck for dinner outside.
- Presentation. Professional photos and a complete, honest listing lift both the rate and the number of weeks booked.
How the season shapes your year
On the Vineyard, income is concentrated in the summer. Most homes rent by the week, often Saturday to Saturday, and the weeks from early July through late August are the most valuable of the year. June and September are the shoulder season, popular with couples and families without school-age children, at lower rates. Many owners also pick up fall and spring weeks, and some homes rent through the holidays.
Weeks you will rent × your average weekly rate = gross rent. For example only: 10 summer weeks at an average of $8,000 a week is $80,000 of gross rent, before management, cleaning and other costs. The occupancy tax is charged to the guest on top.
Costs to plan for
- Management or agency commission, if you use one.
- Turnover cleaning and linens (often charged to the guest as a cleaning fee).
- Utilities, internet, trash and water through the season.
- Maintenance, landscaping, pool service and caretaking.
- Insurance with $1,000,000 of rental liability coverage.
- Supplies: paper goods, soaps, beach gear, replacing what wears out.
Get a real number for your home
Our rental income estimator shows what homes like yours in our collection rent for in peak summer, based on our current rates. For a week-by-week plan for your home, tell us about it and we will put one together, free and with no obligation.
Questions we hear
Is it better to rent by the week or by the night?
On the Vineyard, summer guests expect weekly stays, and weekly rentals mean fewer turnovers and less wear. Shorter stays can fill gaps in the shoulder season. Town rules may set minimums: West Tisbury requires at least two nights.
When should I set next summer’s rates?
In the fall. Many returning families book the same week for next summer as soon as rates are out, and the best weeks go first.
Updated October 2026. General information, not tax or legal advice: rules and rates change, so confirm with the Department of Revenue, your town and your own advisor before acting.