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Here are the things that can go wrong:

1. Cancelation.
Situation: You booked a cottage in advance, but you cannot go due to some emergency (death in the family, illness, jury duty, your house burned down, etc).

Solution: First, you need to become familiar with the cancellation policy of your rental. All respectable cottage owners or rental agencies should have Terms and Conditions document that you sign/agree during the booking process. This document should clearly outline the cancellation policy. In most cases if you can notify the cottage owner in advance, there is chances that the cottage can be re-booked and you will get refunded. Even if your rental dates are getting re-booked, rental agencies still charging cancellation fee that is in $100-$200 range.

Second, you can purchase cancellation insurance. There are multiple brokers that provide such kind of insurance for cottage rentals, e.g. TravelGuard.ca or InsureMyTrip.ca. These companies will insure your trip, but you would need two documents if you want to claim your insurance - prove of payment and prove of accident (death certificate, doctor's note, pink slip, etc). Please note that they will note reimburse your money if you "just changed your mind".

The cost of cancellation insurance is very reasonable - usually less than 5% of your trip cost. For example, I was charged only $75 for my $2,000 1-week vacation at the private cottage.

2. Damage.
Situation: something was broken/damaged during your stay at the cottage. It can be furniture, doors, windows, toilet, roof, etc.

Solution: Terms and Conditions document should outline your responsibilities in case of damage. Most cottage owners should have their own cottage insurance that covers damages caused by renters. Be aware that some cottage owners are not disclosing the fact that the cottage gets rented by the outsiders to their insurance company in order to save money on insurance premiums. In these cases the damage caused by renters is not covered.

Cottage insurance has a deductible that usually equals to your damage deposit. So, if something will go wrong, cottage owner can use your deposit to fix the damage and if it is not enough - claim his/her own insurance.

It is almost impossible to get the insurance from 3rd party for your damage deposit, however some rental agencies provide Damage Protection plan, e.g. RentCottage. The price of such plan is around $50 and it gives you complete coverage (but it does not mean that you can go completely wild :)).

Here are some tips how to make sure that you are not losing your damage deposit:
- inspect the cottage at the arrival and inform cottage owner about all existing damages;
- if you or somebody from your party caused a damage, please inform the cottage owner. First, you always need to be responsible for your deeds and second, you will have a chance to negotiate the price of your damage rather than losing complete deposit;
- upon departure, arrange second inspection with cottage owner or his/her trusted person to make sure that there are no new damages. Ask to put the results of the inspection in writing and keep this document until your damage deposit if fully refunded;

Unfortunately, if the cottage owner does not want to return your damage deposit and you feel that it is not fair, there is nothing much you can do except going to the Small Claims Court and/or sharing your experience on the internet by writing review on the sites like FindCottage.ca.

3. Medical Emergency.
If you live in Canada and renting cottage in Canada, you don't need to worry about your Medical Insurance, since all Canadians are covered by the government. All you need to do is not to forget your Health Card.

If you are travelling from abroad, I strongly recommend you to purchase the medical insurance from travel insurance company (the companies outlined above also provide medical insurance).

Before arriving to the cottage, you need to find out where is the location of the closest hospital. In case of real emergency, call 911 (preferably from the local phone).

Most likely your vacation will go without any accidents, but don't leave everything to chance.