Sophisticatedly Rustic Maine Cottages Overlooking the Sea

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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 porches 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 is Lone Pine Cottage, new siding and windows! The porch and new stairs make this so much easier to climb over the l...
10/19/2026

This is Lone Pine Cottage, new siding and windows! The porch and new stairs make this so much easier to climb over the ledge.

I got this from my porch at Lone Pine Cottage next door.
10/15/2026

I got this from my porch at Lone Pine Cottage next door.

A start.
10/15/2026

A start.

10/15/2026

Listen to the evening crickets. Sigh.

Always a wonder!!
10/15/2026

Always a wonder!!

The sun is setting further to the south now.
10/15/2026

The sun is setting further to the south now.

Every moment is different. A cloud bank enables us to easily pick out Islesboro low below the more distant Camden Hills.
10/15/2026

Every moment is different. A cloud bank enables us to easily pick out Islesboro low below the more distant Camden Hills.

The season winds down with glory...thanks everyone for a wonderful season.
10/15/2026

The season winds down with glory...thanks everyone for a wonderful season.

That's one of two paintings I have at ArtWaves MDI Northeast Harbor Library August Art Show in Northeast Harbor, Maine.
08/07/2026

That's one of two paintings I have at ArtWaves MDI Northeast Harbor Library August Art Show in Northeast Harbor, Maine.

These days are availability as of today:Wednesday, September 16, 2026          Saturday, September 19, 2026 (minimum 3-d...
07/18/2026

These days are availability as of today:

Wednesday, September 16, 2026 Saturday, September 19, 2026 (minimum 3-day Stay, occupancy of 2)

Saturday, September 19, 2026 Saturday, September 26, 2026 (minimum stay 5 days, occupancy of up to 4)

Saturday, September 26, 2026 Saturday, October 3, 2026 (minimum stay 5 days, occupancy of up to 4)

Friday, October 9, 2026 Wednesday, October 14, 2026

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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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