Managing Your Vacation Rental

Think twice about summer guests renting multiple weeks

Written by Elizabeth Weedon
4.5/5 - (21 votes)

Updated October 2023

Most Cape and Islands vacation rental homeowners are willing to rent their homes on a weekly basis during the summer, but they would prefer 2-, 3-, or 4-week ones. In fact, it’s common to see discounts being offered for multiple-week rentals.

There are some obvious advantages. You only have to deal with one business arrangement (one lease, one set of correspondence, etc.) and you are saved the time and expense of a turnover (or more than one). Particularly those managing rentals from afar welcome the opportunity to avoid those costly turnovers and enjoy knowing that there’s only one set of tenants in residence. 

But here are four important issues related to multiple-week rentals to consider.

1. Increased Wear and Tear

Folks who stay in your home for only a week are usually very busy. They eat out a lot and spend very little time inside your home. Thus, there’s much less wear and tear on the home in general and especially the kitchen. During longer stays, however, your tenants settle into the home more deeply, cooking in more often, fully unpacking, and really making themselves at home. They tend to have more requests for items they’re missing. 

2. Cleaning

Homeowners often celebrate the fact that a multiple week rental can save the expense of a turnover cleaning. The problem is that this is not necessarily true. Many professional cleaners, including my own, complain that, unless they are able to keep up with the cleaning on a weekly basis, the house gets too dirty for them to handle in the short amount of time they have at the end of the rental.  Because of that, I have offered my long-term tenants the option to have the cleaning service come in at some point during their stay. I also try to get them to pay for it, but usually they just say, “Oh, that’s okay, we don’t need it to be professionally cleaned while we’re there.” So, then I end up paying for it myself so that my cleaners aren’t overburdened when the tenants leave.

3. Risk of Cancellation

Multiple week rentals are riskier than weekly ones in some ways. If your tenants cancel, for example, it’s a lot more challenging to rebook two or three weeks than it is just one.  We also hear about situations in which a tenant arrives and discovers the home is not a good fit at all, and, again, it’s more difficult for the homeowner to find a last-minute replacement for multiple weeks. 

4. One Tenant = One Guest Review

This may seem petty but given the constant challenge of trying to get guest reviews posted to your listing per season, keep in mind that renting to multiple tenants (on a weekly basis) increases the odds of your getting multiple reviews.  Conversely, if your multiple-week tenant neglects to write you a review, that leaves fewer options to obtain positive reviews.

What are your feelings about multiple-week rentals? 

About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for since 2008, I’ve been a loyal homeowner on the site since early 1998, just a few months after the website was launched by the Talmadges. I grew up summering on the Vineyard and managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation, which I credit with enabling me to hold onto the special property that has been in our family for nearly a century. An enthusiastic member of the WNAV Homeowner Support Team, I endeavor to keep my finger on the pulse of the Cape and Islands vacation rental industry so that I can provide homeowners advice about how to ensure their booking success with us. With owner Joan Talmadge, I am also responsible for editing and writing much of the text on our website, our monthly newsletters, and Homeowner Blog posts.


  • We had a two week rental last summer for the first time. The couple had rented from us for one week the previous year. The couple left the condo immaculate after one week. After two? Oh boy. I do the cleaning myself since we have a small unit and it was challenging after two weeks. And I am talking about regular use, nothing out of the ordinary. So I can attest to that fact. that multiple weeks means heavier cleaning.

    • Thanks for commenting, Louisa. I’m sorry that you had that experience but glad that you shared it with us. You’re lucky that your home is on the small side. The turnover time is the same for all of us, big homes or small, and doubling the time and energy it takes to clean can really be a daunting task.