Entire home

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

Waterfront cottage with kitchen and fireplace

Property grounds - Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage (Bailey Island)

Fridge, microwave, oven, stovetop - Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage (Bailey Island)

Fireplace, books - Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage (Bailey Island)

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.

Exceptional

Entire home

3 bedrooms1 bathroomSleeps 5528 sq ft

Popular amenities

Ocean view
Kitchen
Washing machine
Pet-friendly
Free Wi-Fi
Outdoor space

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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

Ocean view
Kitchen
Free Wi-Fi
Outdoor space

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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

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 Maine Street and LL Bean Flagship Store. 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/biking trails. Visit our Bailey Island travel guide

View more Cottages in Bailey Island

Bailey Island, ME

What's nearby

LL Bean Flagship Store
42 min drive - 49.5 km
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

Getting around

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

Restaurants

Cook's Lobster & Ale House
4 min walk
Erica's Seafood & Lobster Shop
32 min drive
Dolphin Marina & Restaurant
33 min drive
B.I.G.S. Bailey Island General Store
18 min walk
Allen's Seafood
19 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 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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Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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.

More information

9.6

Cleanliness

9.6

Location

8.0

Property conditions & facilities

10/10 Excellent

ROY

14 Oct 2025

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

10/10 Excellent

Jeffrey V.

27 Sept 2025

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

8/10 Good

Lauren B.

4 Sept 2024

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.

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

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

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.

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

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!

8/10 Good

Susan H.

31 Jul 2025

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

19 Aug 2025

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.

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.

10/10 Excellent

Philippa L.

28 Jun 2024

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

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

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 :)