Winter Rentals in Maine – The Ultimate Guide

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Finding an apartment is hard enough as it is, but in Maine, it’s especially difficult.

Speaking from personal experience, I understand the woes of looking for a place to live in the incredibly tight rental market that Maine has. It takes a lot of time, effort, research, and disappointment to finally find a rental that just works, much more for one that you’d actually enjoy living in.

Winter rentals are a popular option in Maine, due to the abundance of seasonal vacation rentals in the state. Unfortunately, they’re not very well-advertised, and pretty hard to find information about.

I’ve put together this Ultimate Guide to Winter Rentals In Maine in hopes of helping anyone on the hunt for a long-term winter rental!

Keep reading for tips on how to secure a winter rental, and also for a list of vacation rental companies that offer Maine winter rentals!

***I’ve been working on putting together more rental guides for the state of Maine. Currently, I have this one and a Complete Directory to Property Management Companies in Portland, Maine. If there are any other regions or situations that you would like to see a guide like this made for, please let me know in the comments!

What Is A Winter Rental?

A winter rental is a home or apartment primarily used as a vacation rental in the summertime but is rented out to a long-term tenant during the winter months.

In Maine, winter rentals are typically available from sometime in October through the end of April or May. They are mostly found along the coast, with the heaviest density between Portland and Wells, and on Mount Desert Island.

Maine has a lot of winter rentals because there is a very distinct tourism season here.

For many coastal towns that rely on out-of-state travelers for business, there is not enough demand for vacation homeowners to continue offering short-term rentals during the winter months. Most local businesses close down, and there is often very few things to do during the winter in many parts of coastal Maine.

Due to this, homeowners will often rent out their property to one tenant for 6-8 months during the winter. This way, instead of letting it sit empty or only have a few short-term rentals during the winter, they still have some revenue coming in.

Summer vacation rentals in Maine are often rented out by the week and can cost anywhere from $1000 to upwards of $15,000 for luxurious high-end houses. The rates for winter rentals are significantly cheaper than what it would be to rent for 4 weeks during the summer.

It’s important to remember that winter rentals are NOT available to “renew” for the summer months, and you will have to move out at the end of your lease. However, if you do get into a winter rental and are a good tenant, you’ll most likely have first dibs on renting again for the following winter.

Tips For Contacting Winter Rental Management Companies

Let me be very frank with you so you don’t set your expectations too high. Vacation rental companies (who you’ll be dealing with for winter rentals) are typically VERY disorganized regarding their winter rentals.

Their websites are often hard to navigate and rarely provide up-to-date information. Some of the websites are so bad that they actually look fake because you’d think there’s no way an actual business would have such a bad website.

Additionally, the employees often do not respond to the first email or phone call. There are a few exceptions to these statements, but overall this has been my experience.

My advice is to never believe what a website says – ALWAYS call or send an email.

The best time to start inquiring about winter rentals is at the end of the summer. I would say August is a great time to start contacting places, although many companies will not have a full list of possible rentals until sometime in September.

1. Calling is better than emailing. Emailing is better than a website contact form. A website contact form is better than nothing.

2. Always include these things in any email, contact form, or voicemail you leave for a company: # of tenants, if anyone smokes, if you have any pets, # of rooms you need, hopeful move in and move out dates, and budget. Don’t be surprised if they end up asking you again at some point, but including this info is likely to get you a faster response.

Here is a template of what I usually send out to companies – you are welcome to copy and paste this to use for yourself! Just change the information to be accurate for your situation.

“Hello,

I am wondering if any of your vacation rentals are available as long-term winter rentals?

I am looking for __ people, non-smokers, no pets, in ____ area. My budget is $____ and I would like to move in sometime in early October, but this is flexible.

Could you please send me a list of what is available?

Thanks!”

3. Keep a spreadsheet of companies you’ve contacted. This way you don’t do double the work of either looking up their website several times or contacting them more than once. Write down details of what they have available, and if nothing, write that down too.

4. If following up with a company, try to reach the same person you were in contact with before.

5. Remember, although the management companies are who you’ll be communicating with, everything from the move-in/out dates, rates, utilities, etc. is decided by the property owners.

If a list of confirmed winter rentals at a company is still being compiled, I urge you to be patient with the management company. It’s perfectly fine to follow up several times if needed, but if they specifically tell you that they won’t have information until a certain date – do not contact them again until that date.

6. Don’t get discouraged. Finding a winter rental is a tedious process, and it becomes especially unpleasant when dealing with annoying rental companies. Stay the course, and keep your sight set on the goal: finding a place to live.

Maine Winter Rentals By Region

Disclaimer: I found all of these companies by scouring through Google in addition to personal experience looking for winter rentals myself. I only included companies that provided confirmation of offering winter rentals. However, I cannot guarantee that they will still be offering them or have any available at the time you contact them. Always do your own due diligence!

If you know of or work for a company that offers winter rentals that is not on this list, please let me know in the comments, and I will add it!

Southern Maine

Apex Luxury Rentals
Cities: Portland, Falmouth, Cape Elizabeth
Phone Number: 207-553-9966
Winter Rentals Page: https://www.apexrentalproperty.com/vacation-rentals-homes.asp?cat=6773

Ashmore Realty
Cities: Peaks Island
Phone Number: 207-766-2981
Winter Rentals Page: https://ashmorerealty.com/property-status/winter-long/

Bayley Vacation Rentals
Cities: Old Orchard Beach, Scarborough
Phone Number: 207-883-5799
Winter Rentals Page: https://www.bayleyvacationrentals.com/winter-rentals

Bayside Rentals
Cities: Old Orchard Beach
Phone Number: 207-934-9180
Website: https://baysiderentals.com/

Coastal Getaways
Cities: York, Kennebunk
Phone Number: 207-363-3939
Website: https://coastalgetaways.me/rentals/

Drakes Island Rentals
Cities: Wells
Phone Number: 207-646-4747
Winter Rentals Page: http://www.drakesislandrentals.com/offseason.html

Garnsey Bros Real Estate & Rentals
Cities: Wells
Phone Number: 207-646-8301
Winter Rentals Page: https://garnsey.com/rentals-lisitings/winter-rentals/

Grand Victorian Rentals
Cities: Old Orchard Beach
Phone Number: 603-948-1944
Website: https://grandvictorianrentals.com/

Higgins Beach Maine
Cities: Scarborough
Phone Number: 207-553-1388
Winter Rentals Page: https://www.higginsbeachmaine.com/vacation-rentals-homes.asp?cat=5764

Kennebunk Beach Rentals
Cities: Kennebunkport, Kennebunk
Phone Number: 207-967-5481
Website: http://www.kennebunkbeachrentals.com/

L. Dewey Chase Rentals
Cities: Wells,
Phone Number: 207-677-2100
Website: https://www.newharborrentals.com/

Legacy Properties
Cities: Portland
Phone Number: 207-370-5479
Winter Rentals Page: https://www.luxurymainerentals.com/category/maine-monthly-rentals

Maine Seaside Rentals
Cities: Biddeford
Phone Number: 207-284-5350
Winter Rentals Page: https://www.maineseasiderentals.com/rental-listings/

Maritime Realty
Cities: Kennebunkport, Kennebunk
Phone Number: 207-967-4246
Winter Rentals Page: https://gooserocksbeach.net/property-type/seasonal-rentals/

Ocean Park Realty
Cities: Old Orchard Beach
Phone Number: 207-937-5054
Winter Rentals Page: https://oceanparkrealty.com/search.aspx?&incmap=1

Pack Maynard Real Estate
Cities: Kennebunk
Phone Number: 207-967-3883
Winter Rentals Page: https://www.pmrealestate.com/winter_rentals

Port Island Realty
Cities: Peaks Island
Phone Number: 207-766-5966
Winter Rentals Page: https://portisland.com/winter-rentals/index.php?lfield33=Monthly%20Rental

Port Properties
Cities: Kennebunkport
Phone Number: 207-967-4400
Website: http://www.portproperties.com/

Portland Maine Rentals
Cities: Portland
Phone Number: 207-774-5358
Website: https://portlandmainerentals.com/listings-pmr/

Rentals Of The Kennebunks
Cities: Kennebunkport, Kennebunk
Phone Number: 207-604-4286
Website: https://rentalsofthekennebunks.com/rentals/

Saco Bay Rentals
Cities: Old Orchard Beach, Saco, Biddeford, Scarborough
Phone Number: 207-204-0063
Website: https://www.sacobayrentals.com/

Salt & Shine Rentals
Cities: Wells, York, Kennebunk
Phone Number: 207-630-1772
Winter Rentals Page: https://www.saltandshinerentals.com/winter-rentals-573943052

Sand Dollar Real Estate
Cities: Kennebunkport, Kennebunk
Phone Number: 207-967-0507
Winter Rentals page: https://www.sanddollarrealestate.com/winter-rentals/

Seashore Property Management
Cities: Old Orchard Beach, Saco, Scarborough
Phone Number: 207-934-3400
Website: https://www.seashorepropertymanagement.com/

Seaside Rentals
Cities: York, Ogunquit, Wells
Phone Number: 207-363-1825
Website: http://www.seasiderentals.com/

Tamarack Rentals
Cities: Old Orchard Beach, Saco, Biddeford, Kennebunk
Phone Number: 207-934-5327
Website: https://www.tamarack-rentals.com/

Midcoast Maine

Camden Accommodations
Cities: Camden, Rockland, Rockport, Belfast
Phone Number: 207-236-6090
Winter Rentals Page: https://www.camdenac.com/rental-properties/long-term-rentals/

Cottage Connection
Cities: Boothbay, Jefferson
Phone Number: 207-633-6545
Website: https://www.cottageconnection.com/

MaineStay Vacations
Cities: Harpswell, Topsham, Brunswick
Phone Number: 207-833-5337
Winter Rentals Page: https://www.mainestayvacations.com/vacation-rentals-homes.asp?cat=10523

Newcastle Vacation Rentals
Cities: Damariscotta, Bristol
Phone Number: 207-563-6500
Website: https://www.mainecoastcottages.com/

On The Water Maine
Cities: Camden, Rockland, Owls Head, Harpswell
Phone Number: 207-236-7710
Winter Rentals Page: https://www.onthewaterinmaine.com/vacation-rentals-homes.asp?cat=6190

Sea Glass Rentals
Cities: Brunswick
Phone Number: 207-406-4953
Winter Rentals Page: https://www.seaglassrentals.com/winter-rentals

Sea Maine Vacation Rentals
Cities: Boothbay Harbor
Phone Number: 207-350-0778
Website: https://www.seamainevacationrentals.com

Downeast Maine

Acadia Magic
Cities: All over Mount Desert Island
Phone Number: Multiple – check website
Website: https://acadiamagic.com/lodging/vacation-rentals.html

Bar Harbor/Acadia Cottage Rentals
Cities: All over Mount Desert Island
Phone Number: 207-288-0307
Website: https://www.bhacr.com/

The Davis Agency
Cities: Southwest Harbor, Bass Harbor, Tremont, Bar Harbor
Phone Number: 207-244-3891
Winter Rentals Page: http://daagy.com/For_Rent/WR.HTM

Downeast R&R
Cities:
Phone Number: 207-374-5444
Website: http://www.rentalsmaine.com/

Harbor Watch Inn
Cities: Swans Island
Phone Number: 919-824-4265
Website: https://www.harborwatchinnswansisland.com/accommodations

The Knowles Company
Cities: All over Mount Desert Island
Phone Number: 207-276-3322
Winter Rentals Page: https://tinyurl.com/knowlesco

LS Robinson Co.
Cities: Southwest Harbor, Bar Harbor
Phone Number: 207-244-5563
Winter Rentals Page: https://tinyurl.com/lsrobinson

Maine Vacation Rentals
Cities: Blue Hill, Brooklin, Deer Isle
Phone Number: 207-374-2444
Website: https://www.mainevacationrentalsonline.com/

Mountain Sea Properties
Cities: Bar Harbor, Mount Desert
Phone Number: 207-244-0066
Website: http://www.mountainseaproperties.com/

Quoddy Properties
Cities: Eastport, Lubec
Phone Number: 207-214-3272
Website: http://quoddyproperties.com/index.html

Rossport By The Sea
Cities: Eastport
Phone Number: 207-773-7000
Website: https://www.rossportbythesea.com/