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

435 Herrick Rd, Brooksville, ME 04617, USA    
(207) 359-8521
 
 

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  1. Welcoming and cozy, each cottage invites relaxation and comfort. All have firepl...
  2. Crow's Nest Cottage, vintage charm, private, two bedrooms, and a view to take yo...
  3. Pumpkin Island Lighthouse is just across Eggemoggin Reach. You can drive there f...
  4. Each cottage has a character of its own...there are some log-style, some shingle...
  5. Cozy and authentic...Maine coast comfort! This cottage is just a few feet from t...
  6. From your Adirondak chair you can watch the schooners sailing up and down Eggemo...
  7. Two bedrooms, kitchenette, porch, living room with fireplace 75 feet from the sh...
  8. All cottages have real wood burning fireplaces. They are distinctive and quite d...
  9. What a magnificent view out over East Penobscot Bay. That's Pumpkin Island Light...
  10. Herricks Landing beach at mid-tide. Here the tide rises and falls between 12 and...
  11. Bring your own kayaks or rent one and have it delivered to our beach....
  12. Our ocean bathing beach has a great view and lots of sand....more at low tide of...
  13. In 1988 the U.S. Dept. of Agriculture awarded this honor to farms that had been ...
  14. The queen bed in Lone Pine Cottage. It has another bedroom that has two twin bed...
  15. Our barn is a neat post and beam, circa mid-1800's. We have special events there...
  16. Our office is in the old hotel now. Staff live there, not guests. It was opened ...
  17. Hike our woodland trails to Lookout Rock in the fall....
  18. Ask for a breakfast basket to be delivered to your cottage either the night befo...
  19. This is the view from the top of Lookout Rock. On a clear day you can see as far...
  20. We offer six individual private rooms in our Hostel@Acorn. This is a slightly qu...

$150
- $397


Book a Room $150 - $397

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5 based on 22 reviews
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Innkeeper/s:

Sally Littlefield

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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 original coastal vacation destinations, it's an historic land grant property. Choose one of ten sophisticatedly rustic one- and two-bedroom historic cottages, scattered along the shore or tucked among the trees. Cottages include period furnishings and cozy linens, living rooms with woodburning fireplaces and offer either kitchens or kitchenettes. Or choose one of six private rooms (with shared baths and public spaces) in the Hostel@Acorn. It's a no-frills, budget-wise option. Relax amid a quiet setting, yet close to the myriad of restaurants, farmers markets, galleries, shops, and attractions on the Blue Hill Peninsula. Bar Harbor is only an hour away.

For more information visit the website.

Rates

$150 to $397

Off Season: $130 to $296

Payment Types Accepted Include Personal Checks, Travelers Checks, Discover, Master Card, Visa, American Express, Cash and personal checks.

    • A Welcome Breakfast Basket Is Available. Ask In Advance So It Will Waiting For You When You Arrive

Amenities

This property has 10 cottages and 1 conference room. The types of beds available include Queen, Twin, Double and King.

  • Bath Amenities
  • Coffeemaker
  • Family/Kid Friendly
  • Fireplace
  • Free parking on premise
  • Hair Dryer
  • Heating
  • Iron/Ironing Board
  • Kitchen
  • Refrigerator
  • Suitable for Events
  • Swimming
  • Wireless Internet Access

Business Traveler Amenities

A number of casual spaces for meetings and seminars. Can host small meetings of 20-45 individuals. Perfect for casual meetings and small corporate groups that benefit from the unhurried and "away from it all" natural setting we provide.
  • Wireless Internet Access
  • Internet Access
  • FAX On-site
  • Desk
  • Hair Dryer
  • Iron/Ironing Board
  • A Number Of Casual Spaces For Meetings
  • Seminars. Can Host Small Meetings Of 20-45 Individuals. Perfect For Casual Meetings
  • Small Corporate Groups That Benefit From The Unhurried
  • "away From It All" Natural Setting We Provide

Events Hosted

    • Honeymoons
    • Weddings
    • Family Reunions
    • Seminars
    • Meetings
    • Romantic Getaways
    • Honeymoons
    • Kayak Getaways
    • Catered Picnics

Foreign Languages Spoken

It varies with staff but possibly German and French.

Parking

Easy, right next to most cottages.

Inns Of Interest

    • Barns
    • Boats
    • Lighthouses
    • Log Cabins/Houses
    • Oldest Continuously Operated Inns
    • Still in the Family

Pet Restrictions

Welcoming a single dog with its humans to Birches Cottage.
  • Pets Allowed
  • Welcoming A Single Dog With Its Humans To Birches Cottage

Romantic Interest

Sunset over ocean & mountains, peaceful natural setting with plenty of space to dream, lawns and gardens, a swimming beach and hiking trails winding to Lookout Rock way above the Sea. Evenings spent by the fire in your cottage living room.

What's Green About Your Inn

Much LED and florescent lighting which saves hundreds and hundreds of dollars in Electric costs. Zone heating in winter offices. Energy efficient equipment as much as possible. Guest amenities are all organic or "green." Use of 100% recycled paper in toilet paper, paper towels, and office products. Low water consumption washing machines. Propane operated driers.

Innkeepers Association Memberships

Maine Innkeeper's Association, Maine Tourism Association, Blue Hill Peninsula Chamber of Commerce

Describe Garden and Grounds

Expansive oceanfront with two beaches, 60 natural acres with mossy wooded areas, hiking trails and great vistas.

Reservation/Cancellation Policies:

Minimum Stay Requirements

Two night minimum although it is more economical to rent on a week-long basis. Arrive any day of the week.

Children Restrictions

Children and families most welcome. Our individual cottages are great for families.

Cancellation

Deposits are fully refundable only if the reservation is changed or cancelled more than forty-five days prior to arrival date (sixty days for reservations longer than two weeks or those that involve more than one accommodation). Deposits for reservations cancelled or changed less than forty-five days prior to arrival date may be refundable, less a $50 cancellation fee, only if we are able to rebook the cottage. Trip insurance is recommended. Substitution of Accommodations: Occasionally through unforeseen circumstances an accommodation may have to be changed. If at all possible, guests are consulted prior to arrival. When a more expensive accommodation is substituted, guests are not charged for the difference. If it is necessary to substitute a less expensive accommodation, the lower price will be charged. Reservation Deposits: At the time of reservation, we require a deposit of 50% of the total reservation including tax and $200 refundable security deposit. The remaining balance is due one month before arrival. We would prefer a check; however we also accept MasterCard, Visa, Discover, and American Express. We require a credit card number to be kept on file for all reservations. Security Deposits: We charge a $200 refundable security deposit, which will be returned two weeks after departure unless there is damage, the cottage is left in poor condition or there was an unauthorized late checkout.

Check-in/Check-out

4:00 PM / 11:00 AM


Other Activities

    • Wineries
    • Water Sports
    • Shopping (Local Crafts)
    • Parks
    • Museums
    • Hiking
    • Golf
    • Fishing
    • Canoeing/Kayaking
    • Birdwatching
    • Bicycling
    • Beaches
    • Art Galleries
    • Antiquing
    • Concerts
    • Musical Events
    • Boating
    • Whale Watching
    • Lobster Boat Trips
    • Schooner Day Trips

Historic Interest

The Oakland House Hotel opened to the Rusticators on July 4th, 1889. It is on property that was King George of England grant land in 1767. The original homestead is a post and beam structure that is within the massive renovation that occurred in 1889 to convert it into a hotel with 32 rooms. We are in our 128th season of welcoming guests. The cottages were built specifically for certain guests over the last Century. The last was build in 1969.

Historic Awards:

  • National Historical Site (Granted)
  • Awarded A Bi-centennial Farm Certificate By The Dept. Of Agriculture In 1976

Historic Memberships:

  • National Trust

Historic sites nearby:

Castine (10 miles)

Recommended Restaurant(s)

Marlintini's (casual dining) in Blue Hill., Barn Castle (pizza/Italian) in Blue Hill, Fisherman's Friend (casual seafood) in Stonington..., Buck's in Bucks Harbor (wonderful fine dining), Arborvine in Blue Hill (fine dining)..

Nearby College/University

Maine Maritime Academy in Castine. WoodenBoat School in Brooklin. Haystack Mountain School of Crafts on Deer Isle. College of the Atlantic in Bar Harbor. Kneisel Hall School of Music in Blue Hill.


Infusion Of Fresh Anise Hyssop And Candied Anise Hyssop Sprinkles

Capture the subtle scents from the summer garden. This is a simple syrup made from fresh anis hyssop leaves and flowers. Dry the candied leaves and chop them for added flavor.


Vanilla Cake For Fresh Anise Hyssop Marscapone Frosting

This is a heavenly summer dessert well worth the time. See separate recipes for my Fresh Anise Hyssop Mascarpone Frosting and Fresh Anise Hyssop Infusion (photo included) on this site.


Fresh Anise Hyssop Mascapone Frosting For Vanilla Cake

Mascapone is like the heaviest cream made into a mild cheese. Add a Fresh Anise Hyssop Infusion and whip until fluffy. Like heaven! Use to frost a delicate vanilla cake (see my recipe on this site).


Lemon Verbena Infusion (a Flavored Simple Syrup)

Superbly delicate, extraordinarily delicious. Lemon Verbena is easy to grow in in a sunny area. Its scent is my favorite in my entire garden. This infusion is good as a sweetener for tea and alcoholic drinks. Use this to make my Lemon Verbena Pound Cake.


Blueberry Compote For Lemon Verbena Scented Pound Cake

This is a marvelous addition to my Lemon Verbena Scented Pound Cake (recipe on this site), but it makes a great sauce for ice cream alone, vanilla cake or a lemon tart.


Lemon Verbena Scented Pound Cake With Blueberry Compote

I adapted this from a traditional Pound Cake and made one 6-cup size loaf. You can double the ingredients and make two. Served with Blueberry Compote and vanilla ice cream, this is a wonderful Maine summer dessert.


Gluten Free Granola With Dried Blueberries



Write a review

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

My ratings for this property      
     Location
     Comfort
     Condition
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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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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      
     Location
     Comfort
     Condition
     Cleanliness
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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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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      
     Location
     Comfort
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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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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 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      
     Location
     Comfort
     Condition
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BOTTOM LINE: I would stay here again.
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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      
     Location
     Comfort
     Condition
     Cleanliness
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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

My ratings for this property      
     Location
     Comfort
     Condition
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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

My ratings for this property      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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 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      
     Location
     Comfort
     Condition
     Cleanliness
     Service
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.

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

My ratings for this property      
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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
     Cleanliness
     Service
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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