Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Bailey Island, Maine
$462 avg/night Minimum Stay 3 Nights
Bed 3

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 5

Max Sleeps

Night 3 nights

Min Stay

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 personbistro 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

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 528 Sq Ft (49 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Near Laundromat Washing Machine
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Garden Porch Or Lanai
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Fitness Facilities Nearby Hiking Nearby Hiking/biking Trails Nearby Swimming Nearby
  • ENTERTAINMENT

    Books Games
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village Near A Hospital Near The Bay Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Availability

Review Review

  • ROY

    Submitted Oct 14, 2025

    Stayed Sep 27, 2025

    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!

  • Jeffrey V.

    Submitted Sep 27, 2025

    Stayed Sep 20, 2025

    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.

  • Jeanne Andrews

    Submitted Aug 19, 2025

    Stayed Aug 9, 2025

    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.

  • Susan H.

    Submitted Jul 31, 2025

    Stayed Jul 27, 2025

    Charming and just right .

  • A guest from Blu....

    Submitted Jul 5, 2025

    Stayed Jun 16, 2025

    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 :)

  • RaeAnn P.

    Submitted Jun 9, 2025

    Stayed Jun 5, 2025

    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.

  • Lauren B.

    Submitted Sep 4, 2024

    Stayed Aug 18, 2024

    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!

  • John W.

    Submitted Jul 19, 2024

    Stayed Dec 31, 1969

    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.

  • Heather P.

    Submitted Jul 5, 2024

    Stayed Dec 31, 1969

    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

  • Philippa L.

    Submitted Jun 28, 2024

    Stayed Jun 24, 2024

    A rustic quaint adorable house. Great views of the water--everything was on the small size, but really do you need anything more?

  • Virginia B.

    Submitted Jun 21, 2024

    Stayed Dec 31, 1969

    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!

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Total

Includes taxes and fees
$462+
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