Pricing your vacation rental correctly is one of the most important decisions you'll make as an owner. Whether you're new to renting or a seasoned pro, setting the right vacation rental pricing strategy can mean the difference between being fully booked early—or scrambling to fill weeks at the last minute.
So should you raise your rates, lower them, or keep them the same this season? Before deciding, ask yourself a few key questions that directly impact vacation rental bookings and profitability.
How to Price Your Vacation Rental for the Upcoming Season
There’s no one-size-fits-all approach to pricing a vacation rental. The best strategy depends on your past performance, your local market, and how flexible you’re willing to be as the season unfolds.
Use Last Season’s Bookings to Guide Your Pricing
Start by looking at how your home performed last year.
- Booked early? If you were fully booked by February, that’s a strong signal you may be able to raise your vacation rental rates.
- Struggled to fill weeks? If you had to discount heavily—or only filled a week or two—keeping your rates the same (or making small adjustments) may be a smarter move.
Your booking timeline often tells you more than your gut feeling.
Compare Vacation Rental Prices in Your Area
Next, take a close look at what similar homes are charging on WeNeedAVacation.
Start narrow, then widen your search:
- Begin with your town, filtering by bedrooms, occupancy, and key amenities.
- Note factors like distance to the beach, updates, and overall condition.
- Expand to neighboring towns, or even the entire Cape or Vineyard, since many vacationers search broadly.
Not every comparison will be apples-to-apples—your home may be newer, while another is closer to the water—but this exercise shows you exactly what vacationers see when they’re deciding where to book.
Vacation Rental Price Caps and Search Filters
Many vacationers search using weekly price filters, which makes round numbers especially important.
If your target weekly rate is $2,000:
- Don’t increase it to $2,050—you’ll disappear from $2,000 searches.
- Don’t lower it to $1,995—you’ll appear after all the $2,000 listings.
Clean, rounded prices tend to perform best and keep your home visible in key search results.
Why Tiered Pricing Increases Vacation Rental Bookings
Not all weeks are created equal, and your pricing shouldn’t treat them that way. Using tiered pricing for vacation rentals allows you to align your rates with real-world demand and maximize bookings across the season.
The highest-demand weeks are typically:
- The last two weeks of July
- The first two to three weeks of August
One of the hardest weeks to rent?
The last week of August, when many families are preparing for the school year.
Pricing that week lower from the start is often more effective than waiting to discount later—when deeper price cuts or an empty week become more likely.
Shoulder Season Pricing Strategy for Vacation Rentals
The shoulder season—especially fall—offers great value for vacationers, but demand is lower overall.
A few things to keep in mind:
- Smaller homes tend to perform better during shoulder season.
- Larger homes (4+ bedrooms) often take longer to book.
- Be prepared to discount significantly, sometimes by as much as half your peak-season rate.
- Offering shorter stays with higher nightly rates can attract more bookings and increase flexibility.
Finding the Right Vacation Rental Pricing Strategy for You
Some owners prefer:
- Lower, steady rates that drive early bookings and repeat guests.
Others:
- Start high and adjust closer to the season through negotiation or targeted discounts.
Both approaches can work. The most successful pricing strategy is the one that aligns with your comfort level, goals, and tolerance for uncertainty.
Get Expert Help Pricing Your Vacation Rental
If you’d like professional guidance, we offer vacation rental pricing consultations—both in-home (often paired with a photography session) and remote.
You’ll receive:
- Comparable rental analysis
- Customized pricing recommendations
- A detailed report tailored to your property and market
Email support@weneedavacation.com to schedule your consultation.