Airport, Portland, ME (PWM-Portland Intl. Jetport)
66 min drive
Rooms & beds
3 bedrooms (sleeps 5)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Double Bed
Bedroom 3
1 Single Bed
1 bathroom
Bathroom 1
Bathtub or shower · Toilet
Spaces
Porch or lanai
Kitchen
Garden
Dining area
About this property
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
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Bailey Island
Located in Bailey Island, this cottage is in a rural area and on the waterfront. Paddleworks and Land's End Gift Shop are local attractions and those in the mood for shopping can visit LL Bean Flagship Store and Maine Street. Ash Cove Pottery and Wolfe's Neck Farm are also worth visiting. Discover the area's water adventures with fishing and swimming nearby, or enjoy the great outdoors with hiking.
Portland, ME (PWM-Portland Intl. Jetport) - 67 min drive
Restaurants
Cook's Lobster & Ale House - 4 min walk
Bailey Island General Store - 18 min walk
Morse’s - 19 min drive
B.I.G.S. Bailey Island General Store - 18 min walk
Holbrooks Lobster Wharf - 24 min drive
Frequently asked questions
Is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
As of 16 Apr, 2026, prices found for a 1-night stay for 2 adults at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage on 12 Jun, 2026 start from S$384, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
On-site parking is available at the property.
What time is check-in at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Check-in begins at 4:00 PM.
What time is check-out at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?
Checkout is at 10:00 AM.
Where is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage located?
Situated on the waterfront, this cottage is steps away from Casco Bay and Cobwork Bridge. Bailey Island Bridge and Mackerel Cove are also within 2 miles (3 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Liked: Cleanliness, property conditions & facilities, communication
The cottage was a wonderful venue of rest and relaxation for us. The cozy living room /kitchen were well supplied. The bedrooms were clean and comfortable. The evening sunsets were spectacular!
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.
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.
A rustic quaint adorable house. Great views of the water--everything was on the small size, but really do you need anything more?
Philippa L.
Stayed 3 nights in Jun 2024
From a partner site
10/10 Excellent
RaeAnn P.
9 Jun, 2025
Ole Greeley Cottage
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This was our second visit. Love the property. Love the area. Met the owner and she was delightful.
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
From a partner site
10/10 Excellent
Heather P.
5 Jul, 2024
Absolutely perfect
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The cottage was clean and had everything we needed to make fresh meals. Beds were comfy. The response time for any questions was so quick. We loved staying at ol’ Greeley cottage
Heather P.
From a partner site
10/10 Excellent
John W.
19 Jul, 2024
Fabulous location and perfectly appointed.
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The cute little cabin was perfect for my wife and me. It's a snug spot where you're not expecting much privacy, but it's ideal if a quaint getaway is what you're after. I spent the days out on my kayak, and we met for lunch nearby at the Salt Cod Cafe for sandwiches and scones. Walking to dinner at Cook's and Sundrenched was amazing.
John W.
From a partner site
10/10 Excellent
A guest from Blue Bell, PA
5 Jul, 2025
Amazing Maine getaway
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We had such an amazing stay at Ole Greeley Cottage. The house had so much character and the beautiful setting could not be beat, right on the water. We spent a wonderful 4 days exploring Bailey Island, including hiking, rock scrambling over the Giant’s Stairs, and kayaking in the sound. It was like being able to sleep in a smaller version of Acadia, but over 2 hours closer and a whole lot less crowded. Plus the proximity to Freeport, Portland, and, Brunswick made excursions into town easy. And finally the service and care from both Maine Stay Vacations and the property’s owner made us feel taken care of the whole time. Highly recommend, and would stay with them again without hesitation. We would give more than 5 stars if we could :)
A guest from Blue Bell, PA
From a partner site
10/10 Excellent
Virginia B.
21 Jun, 2024
Dreaming of Greeley
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Ole Greeley cottage is truly a dream! The cottage itself has the perfect balance of feeling like a typical coastal cottage while being modern and fresh. The energy of the space is calming, especially as it creates an indoor outdoor space when opening the doors to let in the ocean breeze. I came here with my husband and two year old and we could not have been set up for a better vacation than we were here. The property has toddler engagement factors (picnic table, swing, beach access, tub, etc) along with safety factors (locks are up high on all doors to the outside, extra railings on the stairs, etc.). The location could not be better! Imagine pushing your child on the swing while you look over the ocean, ducks passing by, ocean wind in your hair! Cooks is not even a 5 minute walk so very accessible to walk to, and despite being close, we never got the sense it was too busy or loud (which had been a concern for us). It is so clear the care and love that has gone into this property, from the beautiful gardens, to the comfortable beds and pillows, to having fans for guests etc. it truly is an exquisite find!