Services | Discover Reliable Vacation Management

Making life a day at the beach.

Success begins & ends with the right booking formula.

We have spent a completely unnecessary amount of time looking at everything that the vacation management industry does or does not do well.

The processes, the services, the software, the things that get done right and where big improvements are sorely needed.

The universally missing ingredient we found was - NO ONE IS ACTUALLY AN EXPERT ON GETTING YOUR PLACE PROPERLY BOOKED AND MAXIMIZING YOUR RETURNS.

Property managers are everywhere, but nobody was trying to figure out the science to build a successful booking formula. To be very clear - We aren’t property managers - we are booking, calendar & business management experts.

We work with hand-picked on-site maintenance, cleaning and care staff to ensure everything goes off as planned. Everyone stays in their own lane and the results are beautiful.

What Sleepyhouse offers.

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Full calendar management.

Holes in your calendar create big holes in your wallet. It’s all about the right strategy to keep everything properly patched up.

We freely admit that we have spent way too much time in front of screens throughout our business lives. While we are really, really, really trying to change that, we do very much still enjoy purposeful time with technology.
The software suite we have assembled/chosen/built allows us to have the very best of both worlds. Our tech time is now much shorter and always on purpose. Heck, thanks to automation and integrations we don’t even have to be present for a lot of it.
You and your property benefit. While we are keeping our minds clear our tech backend is taking bookings, logging the accounting and growing things better than we could ever do on our own. Pretty sweet stuff.

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Marketing your
property, properly.

This has been our specialty for 20+ years - putting the right message, in front of the right audience, in the right place, to consistently get the right results.

In the vacation property world - you are who the internet says you are. Bad experiences lead to bad reviews which only leads to a bad business model.
There isn’t an online guest in the world who doesn’t look at reviews before they book. So … it is essential to build a mountain of positive reviews with all of your happy guests. It leads to more online conversions, more booked nights and more direct referrals to your property.
We have custom processes to ensure your guests are posting and sharing their experiences both during and after their stay. It really works.
Great repeat visitors are the absolute key to your success. A reliable source of respectable guests to help keep your calendar flush. But having a database filled with great guests goes well beyond just them - you gain access to their own networks as well. A lot of our marketing revolves around sharing offers and opportunities with their friends and family.
Our database is at the centre of our marketing strategy. We access it in a different ways, but always with a set plan and desired outcome. We have created a preferred guest environment that continually works to get direct bookings and take back more control over your own property.
It gets better. Everyone of our vacation property owners has equal access to our years of invested time and good will. If this sounds complicated, we apologize. It is a somewhat confusing and ever-changing world of messaging and marketing. We love discussing how it all works, so for the more detailed version, just reach out and start a conversation with us.
Our database has taken years to build up, but it is a weapon now. A weapon we think you will want on your side.
Social media is a mess. There we said it and you already knew it. The tough part is, it is unfortunately a necessary mess.
We like to run a different program with our brand and our beautiful cottages. The plan is to be inspirational, not transactional. A celebration of everything East coast and a reminder that you should get yourself out here and book a lovely cottage for your stay. No add to cart, no buy now, just a reminder of all the natural beauty and lifestyle that awaits.
It’s simple, it’s a jolt of inspiration to a timeline and guess what - it works.
We track it all and this is the winning formula - Less selling + more happiness = more repeat bookings.
Every marketing action has to have a positive and quantifiable audience reaction - it’s a made-up law we wrote 20+ years ago that has always guided our decision making. If we can’t connect the dots between an action and a desired result, we don’t do it.
Again, it sounds simple, but it isn’t actually common practice.
Our entire strategy is built around loyal repeat guests and their digital/physical word-of-mouth referral. Every marketing action we take is designed to enhance that relationship, not club them over the head with a sales pitch. It has consistently proven to work in both a digital and off-line world.
We LOVE to sit and talk marketing strategy, so please book some time with us to do exactly that. Just don’t have somewhere to go too quickly afterwards, it’s likely gonna be a long talk …
The hardest thing to overcome as a business owner is the world of negativity. A bad experience shared on social media, through review sites or word-of-mouth can be a never-ending obstacle to overcome.
The good news?
The only thing the world likes to share more than a bad experience is a really, really great experience. It’s true.
We seek to leverage your guests on and off-line networks through in the moment social sharing campaigns and creative referral programs. And it really, really works.
We ensure every great experience leads to another.

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Deep dive tracking & reporting.

The needed knowledge to ensure you always make sensible decisions.

Your cottage is a business unto itself.
Every little failure needs to be addressed and corrected and every little success needs to acknowledged and repeated. Little things can become big things in both directions.
Where your guests came from, who they referred, the competitiveness of your rates, and every dollar that came in and out. We track it all for you.
It is all individually tracked to ensure improvements are made and your list of successes can only continue to grow.
In business, there are few things worse than not knowing what is happening with your own investment. Heartless bulk emails, standardized communication and a total lack of personality to everything. Well, we hate it too, so we make sure it never happens to you.
We set a schedule and manner of correspondence with you, that works for you. Prefer phone calls over emails? Done. Prefer weekly rather than monthly chats in busy season? You got it.
Whatever works for your world, that’s the way we like it too. Just old school customer-focused communication.
When you are hyper-focused on your own property, it becomes all too easy to ignore the competition. We’ve been there.
The reality is you are always fighting for eyeballs and bookings from the same pool of vacationers. It is critical to know how your cottage stacks up on all fronts. Amenities & location, pricing & discounts, policies & fees, marketing & reviews - all of these factor into what properties get more bookings.
Our property reports include where you are today and where we think you need to be. We work closely with you to create a roadmap to better exposure, increased bookings and truly maximizing your property’s potential.
Also, watch for our annual vacation reports that are loaded with Atlantic Canada data, analysis and industry trends.
Each month we hit you directly in two spots - your inbox and your bank account. All of your monthly revenue and expenses accounted for, presented and paid out.
On-time, concise and exactly what you need. Like it should be - simple.

Planning to be profitable.

Your vacation property won’t become a successful one by chance. There is a roadmap.

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The big sites charge the big fees. Those fees can increase at anytime and there really isn’t anything you can do about it. That feeling of not being in control of your own promotion and profitability predictions is a tough one to handle. Direct bookings help you minimize the impact of the big booking engines and let you take back control of your own investment.
Each property will have it’s own custom strategy for direct bookings, but the goal is always to build and work our database, then execute purposeful marketing strategies to get you the most reliable, respectful and repeat guests.
Yes, it works, and it’s absolutely necessary to take back control of our own property.
Property maintenance, taxes, repairs, furnishings, improvements - the list of expenses is already a long one for you. That’s why many cottage owners choose to do all of their own management. We totally get it!
Initially it sounds like a great place to save some cash and honestly, the big booking engines sell you on the simplicity of it all. While some properties are easier than others, the simple truth is that they get paid upwards of 20% or more for selling you on a DIY model. Fees galore and you are still doing the management, bookings, accounting, analysis and marketing yourself? Hmm …
What if we told you that you could get complete vacation management services for less than the total cost of a DIY model?
We aim to do exactly that. A simple model jammed with more services, more exposure and more booked nights. And that all adds up to more money for you.
“Did you reach your lifestyle and investment goals for your property last year”? That is a question we love to ask when chatting with a new owner.
The reason we ask is that it gets you thinking and hopefully thinking about your property in a different way. A cottage can be an odd combination between personal/family enjoyment and a revenue source. Juggling both is often an awkward arrangement. For some, lifestyle comes first, for others its cash flow - there is no right or wrong answer here, your annual property goals should reflect your own personal preferences.
Each year, we help you set realistic and workable goals for your property. It’s a productive process and it really helps to keep everyone working towards the same targets.
One of our favourite little tech touches - dynamic pricing software.
It sounds cool, but what it does for your property is way cooler. The software we use allows us to set nightly pricing based on a variety of predetermined rules. The algorithms make the most accurate predictions as to what the correct price should be for a property at any given time. It may sound complicated, but truthfully it is an absolute saviour for us.
Dynamic pricing models help us maximize revenues, occupancy, duration of stay, our own time and always stay one step ahead of competitive properties. It’s the same tech hotels use to make sure they are running the most efficient and profitable business possible. Balancing minimizing empty rooms, while maximizing nightly rates.
The short story is - with all of this data and technology available to you, this is something every serious property owner absolutely needs to be taking advantage of. We love it and use it for every property under our care.

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Concierge for your guests.

We can’t help getting excited about their vacation.

The property world has been our domain for over 20 years. This isn’t just what we do, it’s somewhat shamefully, the only thing we know how to do! It’s a good thing we love it.
This is our get-up and go to work job each and every day. This is not a hobby or a side hustle, it is now our fully dedicated profession.
Your guests benefit from our availability, dedication to getting it right, prompt attention and concise communication.
It’s what a family business is supposed to be. All in.
We admit it, we may have missed our calling. Long ago, like some family members have, we should have fully committed ourselves to being professional tour guides/operators. Catching people on vacation is often catching them at their very best. Relaxed, away from technology, receptive to real conversation and open-minded towards new experiences.
But now we get to make up for it with over-the-top resources and support for our guests!
If they choose, we take this opportunity to shower guests with any and all of the travel and tourism information they could possibly need. The must-go eateries, the secret beach spots, the hidden hiking trails, where to take the dog for an unforgettable afternoon - all of it.
Whatever they need, we are happy to help with some trip planning advice and email over our prepared digital packages.
Your guests feel like an organized insider before they even arrive. It keeps them smiling throughout their vacation and sharing their epic experiences. It all leads to more positive reviews and a measurable increases in future bookings.
We may have missed our calling, but it’s all connected.
What happened to tried and true customer service in this world? Did we somehow forget that customers keep our businesses alive? It’s a business world full of shortcuts, even shorter attention spans and endless transactional behaviour. Yes, it drives us nuts.
While it is sad to see, it is also now a landscape of opportunity. There has never been a better time to double down on what has always worked.
For us, we are fortunate to be catching people at their best - on vacation. We do our best to mirror their enthusiasm with our level of attention to their holiday. If they need something, we get it for them. If they have concerns, we address them honestly. After all, they are the main characters in this story, not us.
We have been putting the customer first for 20+ years, it’s actually the only way we know how to do it.
We talk about this in our marketing section above, but this one here is a little different. It’s about a feeling.
Customers will or will not return because of how you treated them the first time. Did they truly feel like their vacation was important to you? Did you ask about their kids with what they might need? How about their dog? The whole family is on vacation here!
If you didn’t provide the right experience when you had the chance, it simply doesn’t matter how much you market to them in the future.
We want actual experiences to align with our marketing efforts. That feeling of never being forgotten and always important is the key to returning guests and their future recommendations to family and friends.

The back-end to back it all up.

Just trying to stay organized in a sea of change.

This sounds kinda sad, but there is almost we nothing we enjoy more than a perfectly synchronized calendar. Off-line direct friend bookings, reserved family weeks, database bookings on sleepyhouse.ca and international travellers clicking on the big booking engines - this is an awful lot to keep working in perfect unison. Could you imagine messing this up and accidentally double-booking someone’s holiday? Nope, we couldn’t either.
Cancellations, double-bookings, overlapped days - they are all killers to your reputation, reviews and bottom-line.
Here is how we solve it - calendar synchronization software. All of our property calendars are managed from one central location. When a change is made in one spot, it is instantly reflected across all other channels. The software speaks to them all in real-time and ensures that there is truly only one booking calendar for a property.
Take your family days without worry, the problem is solved.
It’s an odd relationship.
We absolutely adore software and apps that both save us time and help us run a tighter ship. But it is a fine line. Technology should never be a substitute for human interaction, at least not in our line of work.
We only aim to use software that encourages human interactions, not seeking to replace them. Go online to line up more offline conversations, that is the goal. We try to keep an open mind towards using the latest and greatest tools to run a better business, while always balancing the potential loss of human interaction as a result.
Vacations are a personal thing. A successful vacation property experience has to echo that.
Artificial intelligence may be all the rage, but we will still believe in the value of human intelligence, thank you very much.
Simple one here, but way too often completely overlooked.
Whatever your preferred method and frequency of correspondence is exactly how we will do it. Sure, we have processes and monthly occurrences that we like to stick to, but it's all of the conversation outside of that that matters.
An evening drink on the patio, a short phone call, a concise email, a semi-personal online video chat, a long series of random text messages - whatever works for you to stay in the loop of what we are doing and how things are going with your property.
We freely admit that we have spent way too much time in front of screens throughout our business lives. While we are really, really, really trying to change that, we do very much still enjoy purposeful time with technology.
The software suite we have assembled/chosen/built allows us to have the very best of both worlds. Our tech time is now much shorter and always on purpose. Heck, thanks to automation and integrations we don’t even have to be present for a lot of it.
You and your property benefit. While we are out high-fiving and assisting guests, our tech backend is taking bookings, logging the accounting and growing things better than we could ever do on our own. Pretty sweet stuff.

What Sleepyhouse doesn’t offer.

On-site property management
We work with different teams in different areas to always get the right results for you and your guests. The right people for the right jobs.
Repairs & maintenance
Again, we work with the best local staff and contractors to help keep your property in tip-top shape.
Cleaning services
We handle the scheduling and the performance, but we don’t do the scrubbing.
Excuses
We know what we are great at, and we are very aware of what we are not so good at. We make sure we stick to what we know and where our talents are best suited.