House holiday rentals in Orr's Island

Waterfront Cottage Getaway-Sunsets, Kayaks, Tennis

Classic, rustic, waterfront Maine retreat (“Crow’s Nest”) perched above Beal's Cove w/i Harpswell Sound w/ private direct waterfront access via steps w/ platform for fun activities - 4 kayaks+2 paddle boards included. Its plentiful sleeping space, porch, and expansive property w/ shared tennis court make it fun for family reunions or get-togethers. Porch speckled w/ rocking chairs overlooks the bay and has spectacular views of sunsets enjoyed w/ coffee, cocktails, and lobster & steamer dinners.

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Sunset Stunner w/summer dock

Relax with the family at this peaceful place to stay. This cozy waterfront home offers a tranquil escape with breathtaking ocean sunset views that paint the sky each evening. Lots of windows and open concept living area provide uninterrupted vistas of the water, allowing golden light to flood the space. The wrap around deck just steps from the water's edge is an ideal spot for morning coffee or evening dinners as the sun dips below the horizon. This charming home blends comfort and nature.

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

oceans edge private home | full AC

Uniquely private location, down the peninsula in Harpswell. Perched on the rocky shore. Open ocean, crashing waves, distant islands, birds and breezes. An uncluttered classic Maine home in a remarkable location. Walk to local cove beach. Secluded. Flanked by two shingled homes only visible through the trees. Two large decks, one covered. Guests and neighbors do swim off the rocks at low tide, but it looks precarious to me. Lounge on the rocks in comfy chairs or just never leave the decks.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Mermaid's Chair | Private Beach | Hot Tub

A classic 1939 Maine camp sitting directly on Casco Bay with a private dock, sweeping water views, and a saltwater hot tub, all on a quiet private road. Properties like this don't come around often, and once you're here, you'll understand why. The dock puts you right on the water, with one slip available for guests. Wolf's Neck State Park and Wolf's Neck Farm are a short walk away, and Downtown Freeport and Portland are just minutes down the road.

Gurnet Summer Home "Beau Sejour"

Welcome to Beau Sejour. Authentic Maine property with two brand new balcony’s overhanging the ocean. Attached to the lower balcony includes a staircase- offering direct access to water/beach. A beautiful seating area and outdoor dining table rests on the upper deck, giving panoramic views of the cove and coastal wildlife. Sunrises are especially beautiful, with frequent sightings of bald eagles, osprey, and seals. An authentic Maine experience.

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Coastal Hideaway - Water views with expansive deck

Coastal Hideaway. Water views with expansive deck, pool table, office area. Fabulous home with lots of open room for relaxation by the ocean. This home, tucked off the road in a private community of Harpswell, is just what you are looking for. With 3 bedrooms, and sleeping for 6, a great family vacation or get away with friends awaits. Pets are not allowed at this property. No smoking is allowed at the property.

Oceanfront Cottage w/ Wharf & Kayaks – Harpswell

Oceanfront cottage on tranquil Basin Cove with a wide private wharf, direct water access, and kayaks. This thoughtfully designed 2BR home features vaulted ceilings, open-concept living, and stunning sunset views. Swim, launch a kayak, or unwind on the deck overlooking the water. Minutes to Mitchell Field Beach, Dolphin Marina, and some of Harpswell’s best seafood and coastal trails.