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Pricing Your Vacation Rental for Maximum Bookings and Profit

Joan Talmadge | Updated 9/26/2025
Pricing Your Vacation Rental for Maximum Bookings and Profit

Go Up, Go Down, or Stay the Same?

That’s the big question for vacation rental owners—whether you’re new to renting or a seasoned pro. Before deciding, start by asking yourself a few key questions:

How were your bookings last season?

  • If you were fully booked by February, consider raising your rates.
  • If you struggled and had to cut prices to fill more than a week or two, keeping your rates steady may be smarter.

What is your competition charging?

Check comparable properties on WeNeedaVacation.com.

  1. Start with your town: enter your home’s bedrooms, capacity, and amenities, and note distance to the beach.
  2. Widen your search: look at neighboring towns or even the whole Cape or Vineyard. Many vacationers search broadly.

Comparisons aren’t always apples-to-apples—your home may be newer, while another closer to the beach may be priced the same. But you’ll get a solid sense of what vacationers see when they weigh their options.

Watch the price caps

Vacationers often filter listings by weekly price. If your target rate is $2,000, don’t push it to $2,050 (you’ll disappear from $2,000 searches) or drop it to $1,995 (you’ll show up after all the $2,000 homes). Round, clean numbers work best.

The benefit of tiered pricing

The highest-demand weeks are the last two in July and the first two to three in August. The hardest week to rent? The last week of August, when school starts up. Price that week lower from the outset—waiting to discount often leads to steeper cuts later, or worse, an empty week. Read more: Maximize Your Bookings with Tiered Pricing

Shoulder season strategy

The shoulder season—particularly the fall—offers many advantages for vacationers. However, fewer families can take vacations during this time of year. As a result, the inventory of available homes goes way up as the demand goes down.

Consider the size of your home. Smaller homes tend to rent more successfully in the shoulder season, while larger homes (4+ bedrooms) are more difficult to book.

  • Be ready to discount—sometimes by as much as half your peak rate.
  • Offer shorter stays with higher nightly rates to attract more bookings.

Finding your comfort zone

Some owners prefer steady, lower rates that attract early bookings and repeat guests. Others start high, then negotiate or adjust closer to the season. Both approaches work—the key is choosing what feels right for you.

Need help?

We offer professional pricing consultations, both in-home (often paired with a photography session) and remote. You’ll get comps, tailored recommendations, and a full report. Email support@weneedavacation.com to schedule.

About Joan Talmadge

About Joan Talmadge: In 1996, my husband Jeff and I purchased our Cape home and began looking for a way to rent it out during the summer. That's when Jeff created WeNeedaVacation, and the rest is history! After teaching fifth grade for 8 years and spending 15 years writing and editing educational publications, I found myself transitioning into a new career as a business owner. Today, we're fortunate to have a wonderful team of capable, caring staff, and Jeff and I are especially proud that two of our three grown children work with us. After 26 summers of renting out our home, we now live here year-round and couldn't be happier. The Cape truly is magical, no matter the season.