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

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

A covered deck with a view of a lake, a grassy area with flowers, and a house in the background.
A cozy living room with a wooden staircase, a leather sofa, a small table, and a guitar.
A coastal view with a clear sky, a grassy lawn, and a body of water.
A kitchen with wooden floors, a dining area with a table and chairs, and a view of the water outside.
A cozy living room with a leather sofa, a blue chair, and a wooden table. There is a large window with a view of the water.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms1 bathroomSleeps 5528 sq ft

Popular amenities

  • Kitchen
  • Pet friendly
  • Free WiFi
  • Outdoor Space
  • Parking available
  • Barbecue grill

Explore the area

View in a map
Bailey Island, ME
  • Place, Cobwork Bridge
    ‪2 min walk‬
  • Place, Bailey Island Bridge
    ‪13 min walk‬
  • Place, beach near Merritt House Road
    ‪18 min walk‬
  • Airport, Auburn, ME (LEW-Auburn - Lewiston Municipal)
    ‪61 min drive‬

Room options

About the neighborhood

Bailey Island

This cottage places you next to Casco Bay and Cobwork Bridge. The cottage includes a kitchen, a fireplace, and a refrigerator.
View more Cottages in Bailey IslandOpens in a new window

What's nearby

  • Cobwork Bridge - 2 min walk - 0.1 miles
  • beach near Garrison Cove Road - 5 min walk - 0.3 miles
  • beach near Channel View Lane - 10 min walk - 0.6 miles
  • Bailey Island Bridge - 13 min walk - 0.7 miles
  • beach near Merritt House Road - 18 min walk - 1.0 mile

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
  • ‪Holbrooks Lobster Wharf - ‬24 min drive
  • ‪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
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 fireplace, a coffee maker, and an ironing board.

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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

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 Land's End Gift Shop within a short drive.

Is parking available on site at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?

No, there isn't parking available at the 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.

Is Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage good for couples?

Amenities that appeal to couples at this waterfront cottage include a fireplace and a kitchen along with a garden.

Are there hot tubs at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?

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.

Are there connecting rooms at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?

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 that I can book at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage?

Yes, every cottage at Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage comes with a porch/lanai and some offer water views.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 10 out of 12 reviews
Rating 8 - Good. 2 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.6/10

Cleanliness

8.0/10

Property conditions & facilities

Reviews

Verified review

8/10 Good

Susan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great cottage and amazing location

Charming and just right .
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

ROY

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!
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Jeffrey V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Jeanne Andrews

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Philippa L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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?
Stayed 3 nights in Jun 2024
From a partner site

10/10 Excellent

RaeAnn P.

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.
Verified review

8/10 Good

Lauren B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 6 nights in Aug 2024
From a partner site

10/10 Excellent

Heather P.

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
From a partner site

10/10 Excellent

John W.

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.
From a partner site

10/10 Excellent

A guest from Blue Bell, PA

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 :)
From a partner site

10/10 Excellent

Virginia B.

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!
Verified review

10/10 Excellent

Nancy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Aug 2024

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