Guide to Bailey-Harpswell-Five Islands-Sebasco-Georgetown Hotels, Motels, and Lodging

Bailey Island, Harpswell, Sebasco Estates, Five Islands, Georgetown, and Westport Island.

Bailey Island is located in the northeastern most part of Casco Bay, beyond Portland and Freeport. The town of Harpswell is here, reached by passing over Orr’s Island via bridge. The Bailey Island Bridge is legendary and one of a kind in the world – its unique cribstone construction allows tidewater to pass through its cribwork of granite stones without the pressure most bridges incur.

Bailey Island is famous for its panoramic ocean views, classic oceanfront dining at The Dolphin, great lobster at Cook’s Lobster Pound and oceanview inns and seaside cottages with warm island hospitality. Popular landmarks include Mackerel Cove – one of the most photographed spots in Maine, and Land’s End -the southern tip of land with a rocky beach jutting out into Casco Bay. 

Sebasco, Westport and Georgetown all offer idyllic waterfront inns and resorts, and lobster shacks from a rustic delicious lunch or dinner by the sea.

Bailey Island Motel | Modern Getaway on Bailey Island 207-833-2886 | 2041 Harpswell Islands Rd, Bailey Island, Maine
Nestled on tranquil Bailey Island and serviced by the world's only cribstone bridge. The Bailey Island Motel has 19 spotless mini-suites with private baths, sitting area, smart tv, mini fridge, microwave, coffee maker, A/C, heat and more. Sit outside your room in your own Adirondack chairs sipping your morning coffee and plan the day's adventures. Enjoy the island's local fare at our wonderful restaurants. Perfect for a couples getaway, family outing, or Maine staycation! Learn More
Coveside Bed & Breakfast | Georgetown 207-371-2807 | 6 Gotts Cove Lane, Georgetown, ME
Coveside is a private, peaceful, upscale retreat on Georgetown’s rocky coast. Get outdoors and enjoy the complimentary kayaks & bicycles, hike the local trails, spend the day at the Reid State Park beaches, or just relax on a waterside lawn chair or hammock and enjoy the stunning sunrise on Gotts Cove and Sheepscot Bay. All rooms have a private bath and lovely cove view. Some rooms have private decks and gas fireplaces. Open year round. Learn More
Riggs Cove House Boat Rentals | Georgetown 207-371-2343 | 340 Robinhood Road, Georgetown, Maine
Stay on a floating house boat in beautiful Robinhood Cove, live on a yacht without the worry of leaving the mooring. Plus you have full service marina, kayaks, a Shoreside Library with free WiFi, and the Osprey Restaurant for lunch and dinner. Four unique house boats are your floating lodging, sleeping for up to 5, with a galley kitchen, bbq grill, deck, and head (bathroom in boat terms). Reach your moored house boat by kayak, canoe or runabout. The dock crew is available daily for assistance. Learn More

Nearby Towns

Flagship Inn & Suites | Boothbay Harbor 207-633-5094 | 200 Townsend Avenue, Boothbay Harbor, Maine
Boothbay Harbor's top rated affordable hotel. Affordable Rooms & Family Suites with easy access to all of Boothbay Harbor & The Botanical Gardens. Less than a mile from the ocean and downtown Boothbay Harbor, on the Trolley Route. Pool, hot tub, complimentary breakfast, playground, picnic area, free Wi-Fi, and direct access to walking trails. Pet friendly. The best value and friendly, knowledgeable staff. Open year round. Learn More
Newagen Seaside Inn | Southport 207-633-5242 | 60 Newagen Colony Rd. , Southport, Maine
Whether you prefer the B&B vibe of our classic rooms and suites, or you want a romantic island getaway in your own seaside cottage, our accommodations are everything you expect from a coastal Maine inn with history and charm. Newagen Seaside Inn is nestled on 20 acres of pristine oceanfront property, at the tip of Southport Island. Minutes from Boothbay Harbor, but far from the noise and crowds. Room rates include breakfast and access to the Inn’s amenities, including pool and vintage game room. Restaurant and bar on property. Open May through October. Learn More
Kennebec Inn | Bath Bed and Breakfast 207-443-5324 | 696 High Street, Bath, Maine
Experience warm hospitality at the Kennebec Inn Bed and Breakfast, located in historic Bath, Maine. Resting on large park-like grounds with an in-ground pool, the Inn is a short walk from a wonderful downtown. Providing many premier amenities of a luxury hotel, while balanced with the personalized treatment and service that only intimate lodging accommodations can provide, the Kennebec Inn has been the B&B of choice by guests of Bath, Maine for over eight years. Learn More
Harbour Towne Inn | Boothbay Harbor - Waterfront 207-633-4300 | 71 Townsend Ave., Boothbay Harbor, Maine
Upon arriving at our quintessential waterfront bed and breakfast you will immediately be transported back to a time when romance and gracious living were a way of life. Choose an Inn room with an outside deck or common deck access for scenic views of the charming village or picturesque waterfront. Our luxurious modern Penthouse is spacious and sleeps four in luxury. Enjoy a full breakfast with our compliments. Fresh coffee, great food and good cheer. Learn More
Cod Cove Inn | Edgecomb 207-882-9586 | 22 Cross Road, Edgecomb, Maine
Perfectly located between Pemaquid and Boothbay peninsulas with all of Midcoast Maine at your doorstep. The Cod Cove Inn offers the privacy of a hotel with the warm, friendly atmosphere of a coastal inn. Four acres of sweeping lawns and groomed gardens, a heated swimming pool in season, and 28 elegantly appointed rooms. Every room offers a commanding panoramic view of the western sky, the tidal Sheepscot River and the village of Wiscasset, Maine’s prettiest village. A deluxe continental breakfast is included in-season; off-season, in-room breakfast is provided. Several pet-friendly rooms. Open year round. Learn More
Bliss Farm Inn | Durham/Freeport 207-407-3241 | 1290 Royalsborough Road, Durham, Maine
Built in 1772, The Bliss Farm Inn is a year-round bed and breakfast that allows guests to take a step back in time without sacrificing any of today's modern luxuries. Located just 10 minutes from Freeport and 15 from Brunswick, Durham is set in the rolling hills and farmland adjacent to the Androscoggin River. Bliss Farm Inn is a special place providing guests true farm-to-table breakfasts, 24 hour snacks and beverages, and all of the simple charms and romance of a historic hideaway! Learn More

Bailey Island Area Inns, Bed and Breakfasts, Hotels, Motels, Cottages, Lodges

Bailey Island Motel l 207-833-2886

Captain York House Bed and Breakfast l 207-833-6224

Clark’s Cottages l 207-743-8560

Driftwood Inn l 207-833-5461

Herrick’s Ocean View Cottages l 207-946-5452

Johnson Cottages and Efficiencies

Log Cabin and Island Inn

Sea Escape l 207-833-5531

Harpswell Area

Bellevue by the Sea Bed and Breakfast

Harpswell Inn l 207-833-5509

Quahog Bay Inn l 207-725-9995

Orr’s Island Area

Little Island Motel l 207-833-2392

Tower Hill Bed and Breakfast l 207-833-2311

Phippsburg Area

Edgewater Farm Bed and Breakfast l 207-389-1322

Hidden Mountain Cottages and Gift Shop l 207-389-1457

Kennebec Kottages l 207-389-1587

Morse River Associates l 207-443-6309

Popham Beach Bed and Breakfast l 207-389-2409

Stonehouse Manor Bed and Breakfast  l 207-389-1141

Five Islands Area
Grey Havens Inn l 207-371-2616

Coveside Bed and Breakfast l 207-371-2807

Friendship Area
Accommodations at Old Comfortable l 207-832-4337

Friendship Harbor House Bed and Breakfast l 207-832-7447

Harbor Hill Bed and Breakfast l 207-832-6646

Georgetown Area

The Mooring Bed and Breakfast l 207-371-2790

Robinhood Cottages l 207-1-2068

Tide’s End Farm Bed and Breakfast l 207-371-9050

Westport Island
The Squire Tarbox Inn l 207-882-7693

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