Sophisticatedly Rustic Maine Cottages Overlooking the Sea

Sophisticatedly Rustic Maine Cottages Overlooking the Sea *NOW TAKING YOUR VACATION "WISHES" for 2026.* See our WISH JAR Process on our website. They radiate with vintage charm yet have comforts galore.

High on a hill, overlooking the sea are Lone Pine and Crow’s Nest Cottages. They were built for guests who came generations ago yet have been updated with amenities and comforts to please contemporary needs. These sophisticatedly rustic log style cottages were constructed from timbers harvested locally nearly a Century ago. They have comfy quilts, “Green” amenities, WiFi, living rooms, covered por

ches with vintage rockers, full baths, full kitchens, two bedrooms and beds to sleep up to 4 adults and 2 children. They are situated in a naturally forested locations with easy walking access to the ocean swimming beach below. From the vantage point of each porch can be seen bald eagles soaring overhead and not far away below is Pumpkin Island Lighthouse, long a beacon for schooners and sailboats plying the waves of East Penobscot Bay. If the relaxation and peaceful surrounds, starry nights, scents of pine, sounds of gently breezes along the shore aren’t enough, the cottages are central to all the cultural attractions of the entire Blue Hill Peninsula. A smattering of attractions are: the New Surry Theater, the Stonington Opera House, Kneisel Hall School of Music, and the hiking trails of Blue Hill Heritage Trust, the Island Heritage Trust, and Maine Coast Heritage Trust as well as Holbrook Island Sanctuary on Cape Rosier. Woodenboat School is but a few miles away. Haystack Mountain School of Crafts a few more. There are amazing restaurants close by in Brooksville, Blue Hill, Sedgwick, Castine and Ellsworth. These cottages are on land that has been in my family since 1767. I am a direct descendant (by marriage) to the original innkeepers who opened their farmhouse to guests on July 4th, 1889. Their farmhouse was largely expanded upon at that time and is now called Oakland House. You will enter my Dreaming of Maine cottage property passing the Oakland House continuing to either Lone Pine or Crow’s Nest Cottage. Normally I take reservations on a weekly basis based upon my traditional Wish List process starting in February. Depending upon how the season progresses there might be short term rentals available. COVID CARE: As of this writing I am not sure what Maine’s COVID requirements will be. I follow the Maine CDC specifications for cleanliness, sanitization and spacing between guest’s occupancies. My policies may change.

This building is refered to as Papa's House. It's  an oft painted scene in Stonington, Maine. The sun changed to overcas...
06/01/2026

This building is refered to as Papa's House. It's an oft painted scene in Stonington, Maine. The sun changed to overcast. I nearly finished this 10 x 10 oil painting but got shivery cold as the weather changed. It was a great day!





For old times sake. I have always loved to garden. I found my old photos (mostly taken in 2007) of the gardens I managed...
05/02/2026

For old times sake. I have always loved to garden. I found my old photos (mostly taken in 2007) of the gardens I managed when Jim and I owned and operated the Oakland House. Dreaming......

I painted that en plein air last fall. Sitting on Little Deer Isle on a chair looking across the ocean at Pumpkin Island...
04/29/2026

I painted that en plein air last fall. Sitting on Little Deer Isle on a chair looking across the ocean at Pumpkin Island Lighthouse. 12 x 12 stretched canvas in oil.





Sunsets are variable and exciting. This was a week or so ago.
04/29/2026

Sunsets are variable and exciting. This was a week or so ago.




The wren couple is back.
04/29/2026

The wren couple is back.


Truely spring!Blue Hill Peninsula Chamber of Commerce
04/29/2026

Truely spring!
Blue Hill Peninsula Chamber of Commerce




Every day is different, yet always the same. Oh glory! It's spring at Crow's Nest Cottage.Blue Hill Peninsula Chamber of...
04/29/2026

Every day is different, yet always the same. Oh glory! It's spring at Crow's Nest Cottage.
Blue Hill Peninsula Chamber of Commerce





There is so much to be thankful for.
02/05/2026

There is so much to be thankful for.

Spring! I'm having a "Spring" moment.
02/02/2026

Spring! I'm having a "Spring" moment.

Thoughts of Spring are creeping into my wakeful day. Memories are sweet.
02/01/2026

Thoughts of Spring are creeping into my wakeful day. Memories are sweet.

Address

38 Oakland House Road
Brooksville, ME
04617

Opening Hours

Monday 11am - 4pm
Tuesday 11am - 4pm
Wednesday 11am - 4pm
Thursday 11am - 4pm
Friday 11am - 4pm
Saturday 9am - 4pm
Sunday 9am - 4pm

Telephone

+12073594645

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