Guide to the Deer Isle, Blue Hill, Orland, Brooklin, and Surry Maine Bed & Breakfasts, Inns, and Hotels

Deer Isle in Penobscot Bay offers charm and mystery all its own. Accessed from the mainland by the 1939 Sedgwick Bridge, Deer Isle is remote – sporting over 112 miles of shoreline between East Penobscot Bay and the Blue Hill Peninsula. Deer Isle was a huge source of granite harvested for the Smithsonian and Arlington Cemetery, now it is home to artists, art galleries and many scenic natural preserves like Island Heritage Trust and Shore Acres Preserve, which protect the natural integrity of the coast.

Deer Isle draws travelers to embark on a similar journey as John Steinbeck’s Travels with Charlie in 1960, he wrote of Deer Isle with haunting affection. Deer Isle hosts frequent farmers markets in summer, and has local seafood restaurants. Staying at Deer Isle you will discover several cozy bed and breakfasts, inns, oceanfront homes and cottages and campgrounds. Deer Isle has a few tour companies offering sea kayak and sailing excursions. Stonington is a classic fishing village on southern Deer Isle, host of the annual Maine Lobsterboat Races.

Blue Hill is a beautiful Maine coast town that has attracted sailors and artists for centuries. Visitors can enjoy a gentle hike up Blue Hill Mountain for grand ocean views or rent kayaks or canoes and tour Third Pond or Blue Hill Bay and the rockbound coast. Visit the Jonathan Fisher House exhibiting the art and life of Fisher who was a farmer, artist, scientist, mathematician, and poet. Play a round of golf at the Blue Hill Country Club. Blue Hill is home to a few lovely inns with excellent dining.

The coastal town of Brooklin in Eggemoggin Reach has a vibrant history, E.B. White – Charlotte’s Web author grew up here and Brooklin is now home to Wooden Boat School and magazine, several boat yards, art galleries and lobster pounds. Bucks Harbor is a quiet boating town at the head of the Reach, home to childrens’ author Robert McCloskey. Nearby Surry is a peaceful, pretty Maine town on the banks of the Union River, near the city of Ellsworth between Downeast Acadia and the Stonington Peninsula. 

Nearby Towns

Captain Nickels Inn | Oceanfront in Searsport 207-548-1104 | 127 E Main St, Searsport, Maine

Enjoy luxury accommodations in a historic Sea Captain’s home. Step back in time and enjoy one of our nine guest rooms as if you were a guest of Captain Nickels himself. Upgrade your stay with one of our suites, both offer stunning views from their decks of our six-acre lawn and Penobscot Bay. Awaken to the smell of our chef’s choice breakfast served each morning in our dining room or solarium. Unwind from a whirlwind day of exploring Maine’s MidCoast in one of our two parlors. Take a stroll to the water and enjoy classic Adirondack chairs on the bay’s edge. Learn More

Pentagoet Inn & Wine Bar | Castine 207-326-8616 | 26 Main Street, Castine, Maine

Gracious hospitality, exceptional lodging, and a cozy pub and wine bar await you. This award winning Queen Anne Victorian inn overlooks the picture perfect village and harbor of Castine. Take one of the inn bikes to Dyce Head lighthouse, hike Witherle Woods or relax at the Backshore beach. Immerse yourself in the beauty of the Maine coast with kayaking and sailing tours around the harbor and Penobscot Bay. Wine Bar open to the public for libations and small plates. Summer Jazz on the Porch, Tuesdays, July-September. Learn More

Blue Hill Inn | Blue Hill 207-374-2844 | 40 Union Street, Blue Hill, Maine

Relax and vacation at The Blue Hill Inn (est. 1840). Visit a quiet town on the picturesque Maine coast. Sail, cruise or kayak past the lighthouses of Penobscot Bay or shop for antiques and visit galleries. Sample food from farmers and fishermen at one of the local restaurants. Then return to a romantic, historic inn complete with fireplacces and a hearty breakfast, drinks and hors d'oeuvres which are always served with "extraordinary hospitality". Learn More

Blue Hill Area
Auberge Tenney Hill l 207-374-2169

Blue Hill Farm Bed and Breakfast l 207-374-5126

Blue Hill Inn l 207-374-2844 l 800-826-7415

Brooklin Area
Brooklin Inn

Eggemoggin Oceanfront Lodge l 207-359-5057

Brooksville Area

Breezemere Farm Inn and Cottages l 207-326-8628

Eggemoggin Reach Bayfront Bed and Breakfast l 207-359-5073

Orland Area
Alamoosook Lakeside Lodge l 207-469-6393 l 866-459-6393

Orland House Bed and Breakfast l 207-496-1144

Shady Oaks Campground/Cabins l 207-469-7739

Sign of the Amiable Pig l 207-469-2561