Holiday rentals in Cutler

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

Seaside Home, Add on Seasonal Bunkhouse for 7!

A peaceful retreat, located at the serene southern end of the island. Our much loved family home, with two bedrooms and 1.5 baths( Bunkhouse offers two bedrooms with beds for 7). Watch the sun rise over the water, while listening to the gulls. A short 3/4 mile walk from beautiful Deep Cove beach. Seasonally, for guests with larger parties, we have just finished our bunkhouse, for an additional fee. Offering beds for 7 and an a generous living space, while sharing the facilities with the house.

Cottage/w beach, hiking, boat lounge, shown on HBO

Overlooking Holmes Bay and lovely Long Point nature reserve, the Dock House is a stylish mini-home connected to a lobster boat library & lounge. Enjoy sun-filled spaces and mid-century modern decor, as well as access to a small beach. Hike some of Maine's best trails (minutes away) or drive to Acadia, Campobello, Eastport, the Schoodic Peninsula and much more. Visit tourist-free coastal towns or go antiquing. Buy fresh lobster, grill on the deck, or dine in-town at renowned Helen's restaurant.

A-Frame, Hot Tub, Firepit, Oceanfront, Pets

Welcome to your coastal escape! Nestled in nature our cozy and unique A-frame retreat is a haven offering, seclusion, privacy and peaceful views of the ocean. Step into our stylish sanctuary where every detail whispers comfort and charm. Overlooking Little Kennebec Bay Bask in tranquility and enjoy panoramic views of the Little Kennebec Bay from your private deck. ✲ Private Hot Tub! ✲ Outdoor Fire pit! ✲ King Bed! ✲ Abundant hiking! ✲ Wood Burning Indoor Fireplace! ✲ Local Kayaking! ✲ Grill

Historic Cottage -Roque Bluffs Beach, Pond, & Park

Relax with your family at our peaceful home just a few short steps from the beach, pond, and hiking trails of Roque Bluffs State Park. Hummingbird Hollow, aka Schoppee House, is a lovingly updated two bedroom cottage nestled between the ocean and state park land. Enjoy ocean views, salt air, and the sound of waves. A quick walk to the beach or pond, you’re not too far away to run back for lunch or take an afternoon nap. Also, the house is fully heated and is suitable for the cooler months!

Gardner Lake home with access and view

Lakefront home steps from Gardner Lake, Whiting, Maine. Tile floors, wood interior, granite countertops, dishwasher, w/d, radiant heat and heat pump. Awesome views/sunsets. Deck/grill. Shared water access with adjacent cabin. Wi Fi. Roku tv - No cable. Message owner for long term rates. Long term stays require references. Extra twin bed and cot in basement living area. Adjacent cabin if available in summer for additional fee. No pets. No smoking of anything or vaping on premises.

The Old Post Office on Cutler Harbor

Beautiful bungalow overlooking Cutler Harbor in Downeast Maine! This old post office has been transformed into a one of a kind oasis for travelers wanting a unique taste of the Maine coast in a serene fishing community. Take advantage of this 2 bedroom, 2 bath property showcasing modern style blended with accents from its former life. Cutler is home to make great hiking trails overlooking Maine’s bold coast, offers boat tours, and is close to ATV trails to explore further Downeast.

Historic comfortable in-town one bedroom apartment

Enjoy an early morning stroll, taking in Lubec's beautiful sunrise, while witnessing local fisherman loading gear for open waters. The peaceful town that gracefully lies on the most east point of Maine. Your three minute stroll back to a peaceful in-town one-bedroom apartment, and enjoy a cup of coffee sitting on your own private deck or enjoying a quiet moment in a historic fishing village apartment. Take in all of the surrounding areas and adventurous things to do.

Ocean View Apartment

This quiet 2 bedroom apartment is roomy and cozy with beautiful ocean views. Use of an outdoor kitchen and patio is available. Newly renovated in April 2025. It is located on a second level so you must be able to climb a set of stairs. You can make day trips to Acadia National Park, Bar Harbor and New Brunswick, Canada. Locally there are State Parks, Hiking trails, and several great restaurants for dining out. Forget your worries in this spacious and serene space.

The Maine Salt River Cottage

This waterfront eco-friendly log home, located in an Audubon Important Bird Area and NWF Certified Wildlife Habitat, comfortably accommodates 6 guests. Perched on a bluff overlooking two of Maine's beautiful tidal rivers, it’s home to bald eagles, osprey, and harbor seals and boasts a dazzling night sky and dynamic water views. Salt River Cottage is a proud signatory of the Glasgow Declaration on Climate Action in Tourism.

The Little Salt Cottage

Welcome to the Little Salt Cottage! Nestled in the charming town plat of St. Andrews-by-the-Sea, enjoy the shops and restaurants of Water Street, stand on the salty ocean shore, and walk along the market wharf...all within two blocks of the home. The perfect East Coast getaway, designed with individuals, couples, and small groups in mind. Find us on social media @littlesaltcottage. We hope to host you soon!

Mary Adeline Cabin at Welch Farm

Drink your morning coffee as you walk the farm's picturesque blueberry fields and shoreline. At night, enjoy sitting around a cozy campfire toasting marshmallows. As you enjoy the scent of fir trees, salt air, and the unspoiled beauty of Downeast Maine, Relax. Spend several days with us exploring the farm or as a jumping off point to venture to other locations around Downeast Maine and Canada.