Home > Maine B&Bs > Brooksville Bed and Breakfast Inns > Oakland House Cottages by the Side of the Sea

Oakland House Cottages by the Side of the Sea      
435 Herrick Rd, Brooksville, ME 04617, USA    
 
 
Innkeeper/s:

Sally Littlefield

Description

Circa 1767. Enjoy this family-owned oceanfront cottage colony on 60 private wooded acres with hiking trails, and panoramic views of the islands and lighthouse in East Penobscot Bay. One of Maine's few remaining o...


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Returning after 20 years

this is just as lovely as it was when I was a child. It's been 20+ years since I've been here last and it's as charming + decadent as it was then, although I swear the Blue Dot Trail [to Lookout Rock] got more difficult :) This time I cam back with my children. It was wonderful to see them look for starfish and crab shells as well as mussels and hermit crabs just as I did. Thank you for this it really felt like home.
Shaina
10/1/2016

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

By the Sea Side

...Yes, I sit here by the Sea Side. Though my stay was short, I am recharged until my return!! A beautiful escape from the Crazy World.
Jim B
9/1/2016

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

#1 Vacation Spot

We can't wait to return, as this may be our new #1 Vacation Spot. Thanks you so much.
Matt and Danielle
9/1/2016

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Our girls have grown to love the trails and sea here

This is our 3rd or 4th visit. It seems the peace, quiet, crisp air is as fresh as the first time we'd stayed (2010??) Our girls have grown to love the trails and sea here - - so different from NJ. What has contributed to our comfort, is without a doubt, the caring and awesome staff. With many thanks for this special time and your kindness.
Julia K
8/1/2016

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

I love it here..

I came to the Lone Pine Cottage with my boyfriend as a last attempt to spend time with him. He will deploy in a few weeks. We have never really been able to have alone time like this and the count down to his departure has really been weighing on my heart. I love it here and I really wanted something for both of us to remember...a moment during this next year that both of us would be able to hold on to.
Jonathan K
4/1/2016

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Fox, Deer, Starfish, Seals & Loons!

Another wonderful week here at the Oakland House, our 17th year and 5th year at Westerly! It's hard to summarize what a week here means to us so, instead, here is a list of notable creatures-great and small-that we observed here at the Reach and around Oakland House in general. Seals Loons Osprey Porpoises (Mother & Calf, another adult) Crabs Starfish Sand Dollars Sea Urchins Squids Egg Case Frilled Anemone Golden Star Tunicate , Baby Lobsters Northern Pipefish, Baby Flounder Rock Gunnel Mink (Eating Crabs) Fox Deer Kingfisher Phosphorescence Thanks to Sally & Jim (RIP) for Sharing their magical place!
Anonymous
8/22/2014

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Guest Musings Whilst Staying at Ledges Cottage

I have been coming to the Blue Hill area since the 50's and didn't know this place existed. What a gem! Our two nights turned into three nights for which we were thrilled. We would highly recommend the hike to Lookout Rock which starts as a yellow blaze from here and then picks up the blue. The view from the top is spectacular and it certainly beats the crowds of Cadillac Mountain. We enjoyed being here so much we did not wander far except for dinner....
Price L
8/21/2013

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Guests' Musings Whilst Staying at Crow's Nest Cottage

This was an awesome week!!! What a great place to spend :) time at. The shore line is magnificent and this cabin is so peaceful. Thanks Sally and all the Staff of Oakland Houe for the Great Vacation.
Lyne E
8/3/2013

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Guest Musings Whilst Staying at Birches Cottage

What a find! We feel so fortunate to have stumbled across Oakland House while searching on the internet for a place to stay w/our dog. Cabin was perfect for our needs while we explored the area. Loved the beach.
Vickey D
7/7/2013

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Clean and quaint

The cabin is cozy and uncluttered, clean and quaint. A definite return! (grateful for the comfortable bed), thanks......
Amy H
9/20/2012

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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (1 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

That Divine Mystery

Henry Beston wrote that, "Nature is a part of our humanity, and without some awareness and experience of that divine mystery, man ceases to be man." We are always grateful for our yearly immersion into that "divine mystery" here at Oakland House.
Christy J
9/15/2012

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Guest Musings Whilst Staying at Westerly Cottage

Our sixth time at Oakland House, second at Westerly. Always hard to leave this idyllic retreat by the sea. We had a wonderful time, as always, and are grateful for all the people who make this magical place so welcoming and soulful.
Dave B
9/12/2012

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Our 5th Stay!

Oh terrible day, we must leave again. Go back to work and stop gazing out to sea, at least for another year.....All of this, I take with me for a suitcase of memories that I can open when needed until next year, to fill up again.
Lorenzo F
9/8/2012

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Guest Musings Whilst Staying at Homestead East Cottage

Oh terrible day, we must leave again (Our 5th Stay!). Go back t work and stop gazing out to sea, at least for another year. Thank-you dear Sally, Heather and Gay for your efforts to make this possible. Warmly, ....
Lorenzo F
9/8/2012

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Buying lobster right off the boat

We loved our stay here at the cottage. It was just soooooooooooooo....pleasant. We sailed out of Stonington and kayaked right off the beach [at Oakland House]; bought lobster right off the fishing boat at the lobster co-op in Stonington and cooked them our last night here!
Janet l
9/1/2012

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Yankees return from the South

We are Yankees who moved south but this place makes us want to come back for good.
Jennifer M
8/4/2012

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Honeymoon

this was my 16th visit to Oakland House, and it was as wonderful as ever! I came with family every summer as a kid, but this time I was here on my honeymoon. and I could show my new husband all the best spots to go tidepooling, to explore, and to sit and daydream, my favorite things to do at Oakland House.
Annie A
9/24/2011

My ratings for this property      
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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Kids Place

We are leaving in the morning after a peaceful, relaxing week. As you can see by what our kids have written, we all enjoy ourselves here.
Elaine S
8/26/2011

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BOTTOM LINE: I would stay here again.
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This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

We will be back

We have dreamt of visiting Maine for quite some time. Our visit here at Shore Oaks and the beautiful countryside surpassed our dreams. We will be back to enjoy it again.
Anonymous
10/21/2008

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Very relaxing!

My wife and I had a great time here. Wonderful room, beautiful setting, very friendly staff. They gladly accepted the free night certificate and we enjoyed it so much that we stayed one more night to partake of the great lobster bake on the beachfront. Dinners were good at the restaurant. The only suggestion we had was that breakfast needed work. They ran out of essentials like OJ and also heard comments from others that it was fairly blah overall.
Ted Cobb
Potsdam, NY
9/3/2008

Management Response
Dear iLoveInns Staff, Mr. Todd send a slightly negative comment amid other very flattering ones. I appreciate his remarks and regret his experience with breakfast. We appreciate that he took the time to comment. This season has been one of changes. For 8 years our daughter and her husband were "in training" to take over the inn. However, last season they decided not to follow in our footsteps. Our daughter was food and beverage director. To take her place we hired a new Food and Beverage Director and hired a well known local Executive Chef who has designed our menus to utilize only the freshest locally harvested and caught ingredients. His experience and qualifications far surpass those of any chefs we've had in the past. He is truly a foodie. He thinks food, breathes food and lives for the marvelous tastes food has to offer. The personalities have changed the mix and also added many new skills. Guests who have been coming for years found changes they did not anticipate and some grumbles did fly about. During the breakfast period we did not have a "manned" omelet station in the dining room as we have in several past years. Sometimes our morning staff did not make clear for instance that guests could order a freshly prepared omelet to their specifications from the kitchen. We regret that we ran out of OJ. I do hope a substitute was made. Mr. Todd was here in July and we were fully up and running so hopefully it was not a staffing issue. All in all guest satisfaction has been high. Our pastry chef is exceptional as is our entire culinary team. Perhaps we will see Mr. Todd again and show that we do pay attention to the details. Kindly look at our web page for our Rusticator Restaurant: http://www.oaklandhouse.com/deer_isle_blue_hill_lobster_dining.html Mr. Todd would have met my son who helped at the lobster picnic on Thursday evening. This was his first season doing so. Respectfully, Sally Littlefield Oakland House Seaside Resort
This response is the subjective opinion of the management representative and not of iLoveInns.com or American Historic Inns, Inc.
My ratings for this property      
     Location
     Comfort
     Condition
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Our favorite place to visit

We have been to Oakland House Cottages many times -- just returned from our 9th vacation there. The cottages are clean and well-kept. All the basics are provided. The kitchens are small but we managed to make a great spaghetti dinner for six, and last year we cooked our own lobster at the cottage. It is unspoiled and "uncrowded". We return as often as possible and hope that they can some day reopen the restaurant.
Barbara Ross

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Relaxing, peaceful retreat.

I actually shed a tear when leaving our beautiful Ledges cottage after a week of a much needed vacation with my honey. Our cottage was perfect and very comfortable and inviting. The beach and shoreline were wonderful and the trail through the woods was magical! No doubt we will be back. -Ed and Michele D.
Michele Bolognesi
Rochester, NY

My ratings for this property      
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BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

At A Glance

22 Review(s)
100% would stay again
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Publicity and Press Reviews

"Sea Lullabies-At these Maine properties, let the sound of the waves coax you to sleep and inspire your dreams...." Yankee Magazine, July/August 2007.
2008 Business Person of the Year. "Presented for a lifetime of contributions"... by the Blue Hill Peninsula Chamber of Commerce to Innkeeper Jim Littlefield.
"This is old Maine, and long may it last." Sunday Eagle- Tribune, September 25, 2005.
Victorian Homes Magazine (Oct. 2006), Sunday Eagle-Tribune (September 25, 2005),
Coastal Living (September, 2004), Newark Star Ledger (July, 2004), Boston Magazine's Elegant Wedding (Summer 2004), Maine Public Broadcasting's "Home; A Place Apart.", Yankee (April 2002), Yankee's Travel Guide to New England (2005), Metroland (August 2002).


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