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.

Family · Location · Nearby

Privacy, River, Pond, A frame Hot Tub EPIC Views,

14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Family · Value · Comfort

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.

Location · Family · Beach

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.

Family · Location · Hiking

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

Location · Family · Bathroom

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!

Family · Location · Cleanliness

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Value · Family · Pool

Waterfront 5 BR Home | On Casco Bay in Freeport!

Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

Value · Location · Pets

Treehouse Farm Stay on the Maine Coast

This memorable location is anything but ordinary. This new, modern space, perched in the trees, overlooks a small-scale farm where the animals are just as well cared for as our guests. Do not underestimate the 600 square foot space. When you step inside, you'll be astounded by the spaciousness, clever use of space, and amenities available to our guests. From an open, sunny living room to an expanded balcony overlooking the duck pond, you'll have plenty of room to unwind and relax.

Family · Location · Nearby

Mermaid's Chair | Private Beach | Hot Tub

*Hot tub not available after October 27- April This is a rare one. 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.

Value · Location · Hospitality

New, 3 Bedroom Home, Orr's Island, ME in Harpswell

This lovely home is now available as a winter rental, no pets. If interested, please message the manager ~ This elite, two- level home is newly constructed, and is situated on Orr's Island with spectacular ocean views from the walls of windows in the home! All furnishings are new, including the beds, as well as appliances ~ Enjoy hiking, kayaking, relaxing on the large deck, which is also fully furnished. A premier getaway, close torestaurants, shopping and fun!

Value · Location · Comfort

In Town Splendor at Castle Rock, Brunswick

Castle Rock is a captivating 3-bedroom, 3-bath family retreat offering waterfront views and convenient in-town living. Immerse yourself in the charm of Brunswick’s scenic surroundings with a 3-mile paved bike path along the Androscoggin river, where eagles soar and sturgeon jump. In a short walk into town, you’ll find all of the restaurants and the activities associated with a college town, with the prestigious Bowdoin College just a mile away.

Family · Location · Bathroom