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“Bucolic, peaceful, absolutely perfect” 5 of 5 bubbles
Review of Oakland House Cottages by the Side of the Sea

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Oakland House Cottages by the Side of the Sea
Connecticut
Level Contributor
55 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
“Bucolic, peaceful, absolutely perfect”
5 of 5 bubbles Reviewed 7 July 2014

Right along the shores of Maine's Eggemoggin Reach, it would be difficult to find a lovelier stretch of shoreline. In the extended Littlefield family forever, the cabins discretely placed around the property, along the shore and in the woods, give one a sense of a time gone by. The cabins are simple but spacious and well maintained and feel a lot like family camps around New England's Northern Lakes 40-50 years ago. It's fabulous.

Room Tip: There are no bad rooms...but near the shoreline is my preference.
See more room tips
  • Stayed August 2013, travelled as a couple
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Rooms
    • 4 of 5 bubbles
      Service
Helpful?
Thank Swb3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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46 reviews from our community

Traveller rating
    39
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    2
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    2
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Rating summary
  • Location
    5 of 5 bubbles
  • Sleep Quality
    5 of 5 bubbles
  • Rooms
    5 of 5 bubbles
  • Service
    5 of 5 bubbles
  • Value
    5 of 5 bubbles
  • Cleanliness
    5 of 5 bubbles
Traveller tips help you choose the right room.   Room tips (13)
Date | Rating
  • English first
  • German first
  • Spanish first
  • Any
English first
Jarrettsville, Maryland
Level Contributor
9 reviews
6 hotel reviews
5 of 5 bubbles Reviewed 6 July 2014

My husband and I stayed at Ledges cottage and it was the most relaxing time of our trip. When we walked down the rock lined path to enter the front door we could not have imagined a more perfect place to stay.....warm, charming, clean, quaint, and just as a Maine cottage should be. My husband commented, "Wouldn't you like to have a place like this?" Nothing was left out of the planning....everything is covered in a brief few pages on the dining room table....then there is a three ring binder with listings of everything to do and where to eat in the area with complete directions. How relaxing it was to light a fire in the fireplace and sit in the most comfortable couch and chairs to read and relax watching the crackling of the fire. We will be returning to Oakland the next time we come to Maine.

  • Stayed July 2014, travelled as a couple
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank csknick
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 10 July 2014
Dankeschön, es war eine Freude, die Sie haben. While I don't speak German very well, my office assistant does. We welcome you and will do all we can to make you comfortable here. Sally
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Switzerland
Level Contributor
32 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 15 helpful votes
5 of 5 bubbles Reviewed 25 September 2012

A friend and I recently stayed in Ledges cottage and loved our time there. The staff were so kind and professional, and everything was incredibly well organized. They had given me a lot of details and help over the phone, and sure enough when we arrived at night everything was waiting for us perfectly as we'd been told. The cottage was cozy, clean, incredibly comfortable (sleep quality was possibly the best ever), and had everything we needed (and more). Not to mention it had so much character and was just a fun place to stay.

The location is beautifully tucked between the wooded areas and the water, which gave it a beautiful and interesting atmosphere. It is private yet not isolated.

If I return to Brooksville, I would definitely stay here again!

  • Stayed September 2012, travelled with friends
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
1 Thank blueeyeslili
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 12 February 2014
Thank-you for taking your time to write your commentary. Yes, Ledges Cottage is beautifully tucked between the wooded areas and the shore of East Penobscot Bay. The king-sized bed is a new pillow top variety and is perfect for real relaxation. We often have honeymooners here because of Ledge's location and size. Guests are charmed by its authenticity and the wonderful environmentally supportive amenities provided right in the cottage.
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Hartford, Connecticut
Level Contributor
47 reviews
19 hotel reviews
common_n_hotel_reviews_1bd8 44 helpful votes
5 of 5 bubbles Reviewed 6 July 2012

Gathered family from Oregon and Massachusetts to celebrate my parent's 50th at Oakland House in late June. Really couldn't have asked for a better experience all the way around! As previous folks have mentioned, it is out of the way but isolated, it is not. New in 2012 is free wifi for each cottage and while it's not up to streaming capability, it does help you keep in touch with the world outside as you feel the need to. Oakland House is definitely a spot for the outdoor lovers and nature enthusiasts. If you're looking for a serene step-back into what "old Maine" vacationing was all about, Oakland House is the place for you!

Our group of 15 included younger kids, young adults, middle-aged parents, and active grandparents. There was absolutely something for everyone. The beaches at low tide had starfish and sea creatures to explore, at high tide there were rocks to leap from into the (briskly cold) water. There were large lawns to play frisbee and wiffleball on and big decks from which to read and enjoy a cup of tea or a glass of wine. There were luna moths to admire during the day and fireflies to catch at night. Most importantly, the space provided just enough togetherness - or alone time - as anyone could have wanted.

Our family stayed at Lone Pine and were able to host most of the semi-potluck suppers on the porch for all to enjoy the purple sunsets from. The kitchen at Lone Pine, while small on counter-space, was well stocked and had a nice large fridge. One reviewer posted that one needed to supply your own cleaning supplies and paper goods - not true! We had an ample supply of all the materials we needed. Lone Pine also has a DISH TV set up, but outside of an international soccer game watched one evening, it never got turned on. Bring board games and cards -- way better way to enjoy the family in front of a crackling fireplace!

The best event of all, however, was our catered lobster "picnic" that was coordinated from beginning to end by the Innskeeper, Sally Littlefield. From helping me choose an over-the-top caterer, to getting the antique barn set up when the weather canceled our beach plans, to providing a most accomodating, friendly and professional staff. She even gathered peonies and other flowers from the on-site gardens! It could not have been a more special event. Not inexpensive, but worth every penny for the memories of a lifetime.

This is not our first trip to Oakland House, and we will definitely be back. My only complaint is that my week went far too quickly. My heart is there still. Thanks Sally!

  • Stayed June 2012, travelled with family
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
1 Thank sierrashoo
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 12 February 2014
We have been welcoming families...now for 125 years. My husband, his parents, their parents and their parents set the stage for these wonderful family reunions. We love these events and the memories that are made for families that are often spread over all parts of the world. And, we would eagerly welcome new families who are seeking just the kind of comfortable, quiet coastal setting as ours.

We are off the beaten track yet well connected to the offerings of the surrounding Blue Hill Peninsula: restaurants, arts, music, theater, nature preserves, hiking, and of course Acadia National Park for a day trip, whale watch, or sight seeing trip to see the crashing surf or vistas from the top of Cadillac Mountain.
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Smithtown, New York
Level Contributor
13 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed 14 July 2011

Went there with the family in early July - I'm still mentally there. The two cabins we were in were great, the Westerly (right on the water near the stairs) and the Grindstone (up the hill). The Westerly is more up-to-date but both are still Maine-style housekeeping cottages. Loved the fireplace in both. The resort is secluded enough on the Eggomoggin Reach but is centrally located between Stonington, Blue Hill, Acadia/Bar Harbor and Bangor, but be prepared to drive at least 30 minutes to an hour in each direction. Kayaking is great with Little Deer Isle in the background. A definite recommendation if you're outdoorsy and love the quiet.

Room Tip: Book early - like right after New Year's.
See more room tips
  • Stayed July 2011, travelled with family
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Cleanliness
Helpful?
2 Thank Bill_Kline
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 12 February 2014
Thank-you for taking your time to write a review. It sounds like your heart never left. So many people feel the same, I guess that is why we have 5 generations of some families returning year after year. We provide a sophisticated rusticity in each of the cottages...all different in design but for sure with beautiful, fresh linens and all the things one might need for a relaxing stay along the shore of Eggemoggin Reach/East Penobscot Bay.
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Albany, ny
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 7 helpful votes
3 of 5 bubbles Reviewed 2 August 2010

We stayed at the Oakland House during the last week of June. The cottage we rented was very clean, very well kept, and right on the water. The area on the Blue Hill peninsula is stunning, when the sun is out. We enjoyed buying lobster right out of the lobster man's garage (although it would have been nice if the cottage had a lobster pot to cook it in - we had to buy one). We took an eco-cruise through Old Quarry adventures which was a lot of fun - saw seals and eagles and great scenery. Also check out the web site for the Flash in the Pan Steel Band, which is a local Steel Band that gives outdoor concerts. They were, totally, totally AWESOME!!!!!
The one thing I think you should keep in mind though, is that Oakland House is very, very, remote. We did not have access to a TV (there are none), computer (of course not - have to go sit in a parking lot about 20 minutes away to access), telephone (our cells did not work here), not even a radio is provided, which really should be so that at least you can get the weather report. The nearest store to buy a newspaper is about 15 minutes away. Personally, I felt a little too isolated. TV, internet and phone I can do without - but no radio and a newspaper was a little much. Also, the place is not on the ocean, but on a bay - not that is a problem, but just be aware of it. Most importantly, they expect YOU to replace the soap, dish washing detergent, toilet paper, etc before you leave with "eco-friendly" brands (no Joy dishwashing liquid for them!). I think this should have been made clear at the time of the reservation. I really don't feel it's appropriate to tell customer's they're responsible for these items (toilet paper and soap? Come one!) AFTER they get there (and the nearest store is 20 minutes away in Blue Hill). I probably wouldn't recommend this place to a friend - we left 2 days early.

  • Stayed June 2010, travelled as a couple
    • 2 of 5 bubbles
      Value
    • 2 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 3 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 1 of 5 bubbles
      Service
Helpful?
4 Thank marci23
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 28 July 2012
My husband Jim was quite ill and we actually closed the business at the end of 2008. But in 2009 he decided that he'd like to rent just a few of the cottages...on a very different basis...self-serve housekeeping. Many of our long time guests were so happy that we still had cottages that they were happy to change the nature of their stays from the prior times of daily housekeeping and meals served in the old hotel.
Jim died in June 2010 and I was in the process of adding more of our vacant cottages to our list of available rental units. My staff and I have learned a little since then as we modify the nature of the business since we closed the restaurant and sold Shore Oaks Seaside Inn. Our cottages are stocked with many if not more of the items normally provided by a BnB, like shampoo, cleaning agents, cosmetic wipes, hand lotion, glycerine soap, paper towels, and toilet paper. We are listed in Maine's directory of "Environmental Leaders." Our products are 100% recycled and organic or eco-friendly.
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Blue Hill, Maine
1 review
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 16 June 2010

It is remarkable that the Littlefield family have been devoted stewards to Oakland House Seaside Resort and its beautiful environs since 1889. They have continued to uphold a long tradition of warmth and hospitality. Sally and Jim's dedicated care of Oakland Resort and its guests is apparent -- from tending sweeping flower beds at the main house (cheerily welcoming all) to maintaining and appointing seaside cottages in very charming ways. Their love of place imbues the resort with an idyllic sensibility. Walking trails on the property have been thoughtfully built, ensuring woodland foraging and lovely vistas. The setting -- stunning coastline -- offers long views of the islands of eastern Penobscot Bay that are truly breathtaking. Oakland House Resort ... to Savor!

  • Stayed July 2009, travelled on business
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
2 Thank friend40522
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
coastalpleasures, Owner at Oakland House Cottages by the Side of the Sea, responded to this review, 12 February 2014
Thank-you for taking your time to write. We love to have folks stay for awhile with us here. This is a sort of ageless destination having been in the same family since the land was granted by King George of England in 1767. The location is stunning with the setting sun sinking over the Bay and disappearing behind the distant hills or islands of East Penobscot Bay.
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Additional Information about Oakland House Cottages by the Side of the Sea

Property: Oakland House Cottages by the Side of the Sea
Address: 435 Herrick Rd, Herricks Landing, Brooksville, ME 04617-3738 (Formerly Oakland House Seaside Resort)
Phone Number:
Region: United States > Maine > DownEast and Acadia Maine > Brooksville
Amenities:
Beach Free High Speed Internet ( WiFi ) Free Parking Kitchenette Pets Allowed ( Dog / Pet Friendly ) Suites
Hotel Style:
Ranked #1 of 2 Speciality Lodging in Brooksville
Price Range (Based on Average Rates): ££
Number of rooms: 10
Official Description (provided by the hotel):
Distinctive and Authentic! This beautiful coastal cottage colony has been welcoming guests since 1889 and has been operated by the same family ever since. With 60 blissfully private acres of coastal woodland trails, beaches, and fields in which to play and dream it's easy to feel like a child again. Ten cottages of rustic sophistication have one or two bedrooms, full baths, living rooms with fireplaces, comfortable furnishings, and full kitchens or kitchenettes. Housekeeping services on a daily basis in season. Two night minimum with a one-week stay being the most economical. Arrive any day, depart any day. We welcome you, your family, and your friends. Perfect for honeymoons, singles and groups events. We welcome a well-behaved dog in Birches Cottage. Other cottages are pet-free and non-smoking, thank you. Open from mid-April through mid-October. ... more   less 
Also Known As:
Oakland House Cottages By The Side Of The Sea Maine/Brooksville

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