Holiday rentals in Monhegan

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Twin Ponds Carriage House

Enter this charming Carriage House which has been totally renovated without giving up its soul. Drenching light from Sunrise to Sunset, Immense french doors with views across the meadow to your private 5 acre pond and Island. Surrounded by Linekin Bay and looking across to Mill Pond as it draws & releases water from the Damariscotta River. The morning sun seems to push you towards the famed East Boothbay General Store where delightful coffees and freshly baked goodies welcome you every morning.

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.

Five Islands Waterfront Retreat

Your ultimate Maine vacation home: Five Islands charm, modern comfort & ocean views. Escape to Five Islands, in our newly renovated home. Designed for relaxation, this property boasts a custom kitchen, expansive deck, air conditioning, and panoramic views of Five Islands. Enjoy unparalleled convenience: 30 second stroll puts you at Maine's iconic Lobster Shack, a public dock, kayak rentals, and a general store. Perfect for families, couples, or anyone seeking a Maine coastal experience.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

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.

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

Cottage on a wharf in a fishing village

Think..ocean, tides, lobster, fishermen, boats, two marinas, magnificent sunrise and sunsets, gateway to Rutherford Island and Christmas Cove, scenery, on a wharf in a working waterfront, friendly locals, buy lobster across the street at Osier’s cafe..eat in privacy on your own deck..magic, educational and authentic Maine!

Comfortable, Cozy, Contemporary retreat

Welcome to Monhegan Island 🌿🐦 Discover coastal charm, dramatic natural beauty, and peaceful surroundings. To visit, please contact Monhegan Boat Line to confirm ferry schedules and book your trip—this is the only way to reach the island, and the ride offers scenic views and occasional glimpses of seals and seabirds.