Holiday rentals in Bristol

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

Ocean-side home on 24 acres (w/ EV+Tesla charger)

Come enjoy the best of what Maine has to offer: beautiful coasts, the smell of pine trees, and salty air. Located on 24 acres of open field, yard, forest, and coastline, this house is the perfect get away for families, small groups, travelers, and more. There's almost always something fruiting (cranberries, blueberries, strawberries, raspberries, blackberries, or stone fruits) and the wild flowers are stunning. The house is cozy but the sea breeze keeps things fresh. Truly a slice of heaven!

Kens Cottage in Round Pond ME

Take it easy at this unique and tranquil getaway. Round Pond is a very special village in Muscongus Bay. It is comprised of a large natural cove filled with an array of boats from working lobster boats to gorgeous pleasure crafts. Located on the Northern Point of Round Pond Harbor the views on the property are stunning. You could be taking in the activity of the harbor in one direction, then watch sailing classes and lobster boats working off Loud's Island in another or just gaze down the bay.

Hermit Thrush House

The 1 bedroom, 1 and 1/2 bathroom with laundry apartment is located at: 19 POORHOUSE COVE ROAD in South Bristol, Maine 04568. The apartment has skylights in the living room and kitchen and is located on a private property as a stand alone guest house. Close to Christmas Cove, Wawenock public/private golf course and 15 miles from scenic Damariscotta and the Pemaquid peninsula with a public white sand beach. Our waterfront is Poorhouse Cove, an estuary off of the Gulf of Maine, Atlantic Ocean.

The Byre at Piper’s Pond

The Byre at Piper's Pond is a small farm situated on 80 acres in Bristol, Maine on the Pemaquid Peninsula. The apartment is separated from the main house and has privacy and room for guests to enjoy the area. It is a comfortable rustic contemporary home and setting. We are located a 10 minute drive to Damariscotta. Pemaquid Peninsula is home to the historic Pemaquid Lighthouse, the University of Maine Darling Marine Center, the Old Fort Henry, Pemaquid Beach and beautiful hiking trails.

Vintage cabin overlooking active lobstering harbor

Stay at Lobster Camp cabins and step back in time. Breathe in the salty air from the deck of your cabin perched on the edge of a true working harbor. Hear the low rumble of boats and watch lobster fishermen unloading their catch. So close to the harbor you feel a part of the action, even from inside. The Halibut, a vintage 1960's 2 bedroom cabin retains its old school charm with minor updates for comfort. 4 cabins in total, this is the 2nd from the water. The view looks like a postcard

Private tree-top loft 5 minutes from Damariscotta.

Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.

Peace and Natural Beauty Surround Round Pond Cabin

Our cozy, well-appointed cabin sits on over an acre of land just a stone's throw from Round Pond, one of the prettiest villages in all of Maine. Walk down to Moxie Cove for a picnic or to Round Pond for great coffee, seafood, and nostalgic Granite Hall store. Great for nature lovers and people who just want to get away from it all. Private deck and BBQ grill, wild blueberries galore, ping pong in the barn and fleeting deer all bring one back to old-time Maine.

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.