Part of the Short-Term Rental Management Guide, step 2: compare
How to Use This List
Send the questions before a call, or work through them during one, and ask for the key answers in writing. The contract is what counts, so check that the answers match it. A good manager will be glad you asked; a vague answer on fees or exit terms is itself an answer.
Fees and Money
1. How Is Your Fee Calculated?
Why it matters: "A percentage" can mean very different things. Is it a percentage of gross bookings, of the rent only, or of net after platform fees and cleaning? On the same booking, those produce different dollar amounts. See how management fees work.
2. What Is Included in the Fee, and What Is Billed Separately?
Why it matters: Photography, listing setup, linens, supplies, hot tub service, snow removal and maintenance visits may be included or extra. Ask for a list.
3. Do You Mark up Vendor Invoices or Supplies?
Why it matters: Some managers rebill at cost; others add a margin. Either can be fair if disclosed. You want to know before the first invoice.
4. Is There a Setup, Onboarding or Minimum Fee?
Why it matters: One-time charges and monthly minimums change the math in a slow first season.
5. Who Keeps the Guest Cleaning Fee?
Why it matters: The cleaning fee guests pay may go to the manager, the cleaner or you. Know where it lands and whether the management percentage applies to it.
6. When and How Am I Paid?
Why it matters: Payout timing, whose account the platform pays, and how the manager's fee is taken all affect your cash flow and your tax records.
The Contract
7. How Long Is the Contract, and Does It Renew Automatically?
Why it matters: A long term or auto-renewal can lock you in through a season you wanted to change.
8. Whose Account Will My Listing Live On?
Why it matters: If the listing is on the manager's account, its reviews and history may not come with you if you leave. On Airbnb, a manager can instead work on your listing as a co-host with full access, and Airbnb says only the listing owner controls payout methods and taxpayer information (help center, October 2026).
9. Which Platforms Will You List On?
Why it matters: More platforms can mean more bookings but also more fee structures and calendars to sync. Compare Airbnb vs Vrbo.
10. Who Is Responsible for Licenses, Registrations and Lodging Taxes?
Why it matters: In New Hampshire, Massachusetts and Vermont, the state tax and town rules differ, and platforms collect some taxes but not always all. Agree in writing who registers, files and pays. Start with the permits and licenses overview.
Reporting
11. What will I see each month, and can I log in anytime?
Why it matters: Bookings, payouts, expenses and maintenance should be visible without asking.
12. Who Is My Contact, and How Quickly Do They Respond?
Why it matters: A named person who answers is worth more than a portal you cannot get a reply from.
Cleaning and Maintenance
13. Who Cleans, and How Are They Trained and Checked?
Why it matters: Cleaning drives reviews. Ask whether cleaners are employees, contractors or a mix, how new cleaners are trained, and who backs them up.
14. Is There an Inspection After Every Stay?
Why it matters: Damage found the same day can be documented and claimed in time. Damage found three guests later usually cannot.
15. How Far Is Your Nearest Crew from My Home?
Why it matters: In winter, drive time is response time. Ask for a real number.
16. What Is the Repair Approval Limit?
Why it matters: You want the manager to fix a broken toilet without calling you, but not to approve a new water heater without you. Agree a dollar threshold.
Pricing and Bookings
17. How Do You Set Prices, and How Often Are They Reviewed?
Why it matters: New England demand swings hard between ski weeks, mud season, July and foliage. Ask which tool they use and how often a person looks at the rates. See seasonal pricing.
18. What Minimum-Night and Cancellation Rules Will You Use?
Why it matters: These shape who books and how much risk you carry when plans change.
19. Will You Take Mid-Term (30+ Night) Stays?
Why it matters: Monthly guests can fill slow seasons, but they bring different rules and taxes. Read mid-term rentals in New England.
Owner Stays
20. How do I block dates for myself, and is there a limit?
Why it matters: Some contracts limit owner stays in peak season or charge a cleaning fee for them. Know the rule before you plan Christmas at the ski house.
Guests, Damage and Safety
21. How Do You Screen Guests and Handle House Rules?
Why it matters: Party prevention, pet policies, maximum occupancy and quiet hours protect your home and your neighbors.
22. What Happens When a Guest Causes Damage?
Why it matters: Ask who files the platform claim, how fast, and what happens if the claim is denied. Check your own insurance too: see insurance and safety.
Exit
23. How Do I End the Contract?
Why it matters: Notice periods, termination fees and what counts as cause all vary.
24. What Happens to Future Bookings When I Leave?
Why it matters: Bookings made months ahead for ski or lake season are valuable. Agree who honors them, who is paid for them, and how the listing is handed over.
Red Flags
- Fees that cannot be explained in two sentences.
- No written repair approval limit.
- Any promise of a set income or occupancy.
- No clear answer on who owns the listing.
- Long contracts with steep exit fees and no performance review.
How New England Host Co Answers
You can put all 24 questions to New England Host Co. Some of the answers: housekeeping and an inspection after every stay; pricing reviewed daily with PriceLabs; every home within 45 minutes of its crew's base; owners pay license and permit fees, consumables (rebilled at cost), utilities, owner stays and repairs, with a repair approval threshold agreed with each owner. Pricing for management is quoted privately. Ask for a free property analysis or call (978) 672-4578.
Back to the owner hub.
FAQ
What Is the Single Most Important Question to Ask?
How the fee is calculated and what it includes. Two quotes with the same percentage can produce very different payouts.
Should I Ask for References?
Yes. Ask to speak with a current owner whose home is similar to yours, ideally in your town or season.
Is a Longer Contract a Bad Sign?
Not by itself. It depends on the exit terms. A reasonable notice period and clear handling of future bookings matter more than the term length.
Should I Get the Answers in Writing?
Yes. Anything that matters to you should appear in the contract, not only in an email or a call.
