Entire home

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

Waterfront cottage with kitchen and fireplace

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

Fridge, microwave, oven, stovetop
Interior
Fridge, microwave, oven, stovetop
Terrace/patio
Fireplace, books
Ole Greeley Cottage offers a classic, charming retreat on Bailey Island with ocean views from the wrap-around covered porch and outdoor picnic table. Unwind in the open concept kitchen, living, and dining area with many windows or explore Harpswell's surrounding towns.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms1 bathroomSleeps 5528 sq ft

Popular amenities

  • Barbecue grill
  • Washer
  • Fireplace
  • Kitchen
  • Pet-friendly
  • Parking available

Add dates for prices

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

Waterfront cottage with kitchen and fireplace
This smoke-free cottage features a garden and barbecues. The cottage boasts a fireplace and offers free WiFi and a kitchen. Guests can appreciate conveniences, such as a washing machine and a fridge, and other amenities include a microwave and a stovetop.
Guest accommodation at this cottage offers fireplaces and coffee/tea makers. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils.

Bathrooms include baths or showers and hairdryers. Guests can surf the web using complimentary wireless Internet access.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • 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

  • Smoke-free property

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

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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

Pets are allowed
Service animals are welcome, and 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
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
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

Property is also known as

2769-260913

About the area

Map
Bailey Island, ME

What's nearby

  • Cobwork Bridge - 2 min walk - 0.2 km
  • Bailey Island Bridge - 5 min walk - 0.5 km
  • Mackerel Cove - 4 min drive - 2.2 km
  • Paddleworks - 4 min drive - 2.2 km
  • LL Bean Flagship Store - 42 min drive - 49.5 km

Getting around

  • Brunswick Station - 30 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 67 min drive

Restaurants

  • ‪Dolphin Marina & Restaurant - ‬33 min drive
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Cook's Lobster House - ‬4 min walk
  • ‪Holbrooks Lobster Wharf - ‬24 min drive
  • ‪B.I.G.S. Bailey Island General Store - ‬18 min walk

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 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).

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Reviews

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

9.8

Exceptional

9.6

Cleanliness

9.6

Location

8.0

Property conditions & facilities
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

Reviews

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

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

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
This review comes from a trusted partner site and has not been verified.

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.

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

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
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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 :)
This review comes from a trusted partner site and has not been verified.

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!

10/10 Excellent

Nancy K.

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