Oceanside stay.Your stay at this cottage will put you steps from Cobwork Bridge and a 5-minute walk from Casco Bay. Also, Bailey Island Bridge is within half a mile (1 km) and Mackerel Cove is within 2 miles (3 km).
Portland Intl. Jetport Airport (PWM) - 62 min drive
Restaurants
Dolphin Marina & Restaurant - 33 min drive
Cook's Lobster House - 4 min walk
Holbrooks Lobster Wharf - 24 min drive
Slow Bell Cafe - 187 min drive
B.I.G.S. Bailey Island General Store - 18 min walk
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
Property manager
Marcia Giles
Languages
English
Similar properties
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
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
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.
Property is also known as
2769-260913
Frequently asked questions
How close is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage to the airport?
This cottage is 44.3 mi (62-min drive) away from the Portland Intl. Jetport Airport (PWM) airport, the closest popular airport to the property.
Does Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage have an airport shuttle?
Airport shuttle services are not available at this cottage.
How close is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage to the beach?
This cottage is 14.1 mi (31-min drive) from Thomas Point Beach.
Does Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage offer free breakfast?
This cottage does not offer free breakfast.
Is there a casino at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
No, there is no casino at this cottage.
What time is check-in at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Check-in begins at 4:00 PM.
Is there free parking at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Free parking is not available at this cottage.
Does Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage have a pool?
This cottage does not have a pool.
Does Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage have a spa?
There are no spa services available at this cottage.
How close is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage to downtown Bailey Island?
This cottage is 0.7 mi away from Bailey Island.
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage Reviews
Reviews
9.6
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. 7 out of 9 reviews
10 - Excellent
7
Rating 8 - Good. 2 out of 9 reviews
8 - Good
2
Rating 6 - Okay. 0 out of 9 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 9 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 9 reviews
2 - Terrible
0
9.6/10
Cleanliness
Reviews
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?