LL Bean Flagship Store - 42 min drive - 30.8 miles
Getting around
Brunswick Station - 30 min drive
Portland Intl. Jetport Airport (PWM) - 67 min drive
Restaurants
Dolphin Marina & Restaurant - 33 min drive
Cook's Lobster & Ale House - 4 min walk
Erica's Seafood & Lobster Shop - 32 min drive
B.I.G.S. Bailey Island General Store - 18 min walk
Holbrooks Lobster Wharf - 24 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Welcome to Ole Greeley Cottage, a charming, classic Maine cottage with stunning ocean views over Merriconeag Sound. You'll love waking up to the sights and sounds of the ocean, exploring Harpswell and the surrounding towns and retreating to the cottage to catch the gorgeous Bailey Island sunset paint the sky with red, orange and purple from the wrap-around covered porch. Don't miss the opportunity to dine al fresco on the water's edge at the outdoor picnic table that seats 8, and a two person bistro set.
Inside the cottage you'll find an open concept kitchen, living, and dining area with many windows and a sliding glass door opening to the ocean and covered porch. The kitchen offers a farmhouse sink, large retro refrigerator, gas range, microwave and all the cooking/dining ware needed to prepare and enjoy a delicious homecooked meal. The dining table seats 4-6 and the living room offers a large leather sofa and two wicker chairs, the perfect spot to read a book, play a game, or delight in conversation with friends. The owners have shared with guests a broad collection of books, puzzles, and board games, inviting all to relax and enjoy the slow-pace of island life.
Located on Garrison Cove Road on Bailey Island, guests will love the ability to walk to Cook's Lobster & Ale House just down the road, as well as Cook's Wharf offering lobster fresh off the boat. Step off the dock onto the Schooner Alert for a sunset cruise around the islands or watch the lobstermen and sailboats cruise by from the porch. The cottage is also just a short walk/drive away from Cedar Beach, The Bailey Island General Store, Fishnet Cafe, Land's End Gift Shop, Sundrenched restaurant, Historic Cribstone Bridge, Salt Cod Cafe, H2Outfitters for kayak rentals/tours, and so much more!
Come to Ole Greeley Cottage and enjoy all Bailey Island and Harpswell have to offer. We're sure it will beckon you back for years to come!
Ole Greeley Cottage is pet-friendly (2 maximum, well behaved), a non-refundable pet fee does apply.
Please note - Although recently renovated/updated, the cottage was originally built in the early 1900's and the interior walls dividing the bedrooms are thin/not insulated, allowing sound to travel more easily than a modern home. Also, the primary bedroom has a custom headboard that is open to the stairs to the first floor. We hope this information is helpful as you prepare for your stay at this charming cottage!
**Important Information Regarding Water Usage** Due to the proximity to the beautiful, rocky coast, the water supply for the cottage is a water storage tank rather than a traditional well. Water is delivered to the property on a regular basis, but guests should be particularly aware of their water consumption and make every effort to conserve this precious resource. While you may use the water comfortably, we ask that you please not run water unnecessarily (i.e. keeping showers brief, turning water off while brushing teeth, not running water constantly while doing dishes, etc.).
Bedrooms: 2nd Floor: Primary BR- Queen Bed with Ocean Views Second BR- Double Bed with peeks of the Ocean Third BR- Twin Bed with peeks of the Ocean
Bathrooms: 1st Floor: Full BA with medium sized shower/tub combo
Air Conditioning: No Water Access: Direct, on property via private stairs Beach Towels: Not included Departure Cleaning: Included Closest Shopping Village: Brunswick, 15min away Coffee Maker: Yes, Regular Drip Dishwasher: No Grill: Gas Grill available, Propane provided Heat Source: Propane Heat Stove on 1st Floor, controlled by thermostat Internet Access: Yes, Xfinity Cable Internet and WiFi Linens & Bath Towels: Included Lobster Pot: Yes Outdoor Firepit: No Parking: 1-2 cars Trash Removal: Included TV: No (guests are welcome to bring their own laptops/ipads to connect to the internet for tv/streaming entertainment) Washer & Dryer: No, laundromats nearby in Brunswick 15-20 min away Water Frontage: Direct ocean frontage Water Source: Water tank, bottled drinking water recommended
The cottage is heated and features a kitchen and space to spread out with 3 bedrooms. Guests can expect to find free WiFi. Other standard amenities include a washing machine, a fireplace, and a coffee maker.
Property amenities
Internet
Available in the cottage: Free WiFi
Parking and transportation
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Lobster/crab pot
Microwave
Oven
Refrigerator
Stovetop
Toaster
Dining
Dining table
Bedrooms
3 bedrooms
Bedsheets provided
Bathroom
1 bathroom
Bathtub or shower
Hair dryer
Towels provided
Living spaces
Dining table
Fireplace
Living room
Entertainment
Books
Games
Outdoor areas
Barbecue grill
Firepit
Garden
Porch/lanai
Laundry
Laundromat nearby
Washing machine
Comfort
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoking not allowed
Services and conveniences
Iron/ironing board
Location highlights
In a rural location
In a village
Near a hospital
Near the bay
Near the ocean
On the waterfront
Things to do
Birdwatching nearby
Fishing nearby
Hiking/biking trails nearby
Swimming nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Unit size: 528 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
This property welcomes pets
Service animals exempt from fees
Children and extra beds
Children allowed: ages 0-17
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Property is also known as
2769-260913
Frequently asked questions
What can I see within easy reach of this cottage?
This cottage is located in Bailey Island, just steps from Casco Bay and Cobwork Bridge, and within a short walk of Bailey Island Bridge. You'll also find Mackerel Cove and Paddleworks within a short drive.
Is parking available on site at this cottage?
No, there isn't parking at this cottage.
Is this cottage next to a casino?
No, this cottage is not connected to a casino.
Will I find an indoor pool at this cottage?
No, there is no indoor pool at this cottage.
What will couples enjoy most about a stay at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Amenities that appeal to couples at this waterfront cottage include a fireplace and a kitchen in each accommodation with some featuring ocean views.
Does Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage have a hot tub?
No, there isn't a spa tub at this cottage.
Does this cottage offer breakfast?
No, this cottage doesn't offer breakfast.
Will this cottage allow pets to stay free of charge?
Although pets can't stay for free, they are welcome at this cottage.
Does this cottage have connecting rooms?
No, this cottage doesn't feature connecting guestrooms.
Where is the closest airport to this cottage?
The closest major airport to this cottage is Wiscasset, ME (ISS), which is 26.5 mi away (44 minutes by car). Another top airport is Portland Intl. Jetport Airport (PWM), which is around 17.3 mi away.
Are there rooms with balconies at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Yes, every accommodation at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage comes with a porch with some featuring ocean views.
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 10 out of 12 reviews
10 - Excellent
10
Rating 8 - Good. 2 out of 12 reviews
8 - Good
2
Rating 6 - Okay. 0 out of 12 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 12 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 12 reviews
2 - Terrible
0
9.6/10
Cleanliness
8.0/10
Property conditions & facilities
Reviews
10/10 Excellent
Jeffrey V.
Sep 27, 2025
Liked: Cleanliness
Such a beautiful cozy cottage with a lot of character. Quite neighborhood and a lot of walking areas to take our dog. We loved sitting out on the porch watching the lobstermen and all the boats. Close to Cook’s Lobster House and Sundrench, both good restaurants.
Jeffrey V.
Stayed 7 nights in Sep 2025
10/10 Excellent
Jeanne Andrews
Aug 19, 2025
Liked: Cleanliness
We were more than happy with the location! It was our favorite part of the day, as we sat every morning and evening on that lovely porch. Cottage was spotless and very comfortable and the owners a delight to work with. The cove beach at the end of the street was a favorite for both four leggeds and two leggeds as was the walk over the bridge for scones at Salt Cod Cafe.
Jeanne Andrews
Stayed 7 nights in Aug 2025
8/10 Good
Susan H.
Jul 31, 2025
Liked: Cleanliness
Great cottage and amazing location
Charming and just right .
Susan H.
Stayed 4 nights in Jul 2025
8/10 Good
Lauren B.
Sep 4, 2024
Liked: Cleanliness
Enjoy the Simple things
Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street!
Lauren B.
Stayed 6 nights in Aug 2024
10/10 Excellent
Nancy K.
Aug 30, 2024
Liked: Cleanliness
Nancy K.
Stayed 4 nights in Aug 2024
10/10 Excellent
Philippa L.
Jun 28, 2024
Liked: Cleanliness
Adorable cottage on the water
A rustic quaint adorable house. Great views of the water--everything was on the small size, but really do you need anything more?