Holiday rentals in Cutler Harbor

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Top-rated holiday rentals in Cutler Harbor

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Guest favourite
Home in Cutler
5 out of 5 average rating, 14 reviews

Coasters' Chance - The Maine Cottage

WELCOME to our NEW cottage located in Cutler Maine! Perched at the end of a private road, this restored 1760's captain's cottage offers seclusion and luxury with an ode to Maines' dramatic coastline. Featured on Discovery Plus - Magnolia network - Point of View a Designer Profile. Season 2 episode 5. Coasters' Chance has been in the Moore family for over 30 years, and has finally returned to its former glory with a modern twist. A recently renovated barn transforms this captain's cottage into an entertaining paradise. Positioned on its own peninsula overlooking Cutler harbor, Coasters Chance offers more than just a getaway. With private access to Bold Coast hiking trails, 190 degrees of waterfront and complimentary fresh lobsters delivered by the locals themselves, we promise you'll leave your heart in Maine. UNIQUE FEATURES: 190 degree water views, secluded location, private access to hiking trails, gourmet kitchen, complimentary fresh lobsters for one night, close to Puffin Tours and Whale Watching. NOTES: The cottage sleeps 8 comfortably—with 3 bedrooms. One with a King suite, one with a Queen suite. The kids room upstairs is located off the original 1700's staircase. She is very steep so we recommend only kids & young adults stay up there. This room has two single beds & 1 double bed, each separated from one another with a bathroom. All bedrooms are incredibly well-appointed. Each bed is decked out in the usual Moore House upgrades: a mattress topper and luxury linens that you’ll wish you could take home with you. The large barn conversion & main bedroom upstairs are not winterized. We suggest from Oct 1st onwards that the house only sleeps 6 unless the weather is fabulous.

Top guest favourite
A view from a deck overlooking Holmes Bay, showcasing a grassy landscape with colorful foliage. A modern mini-home resembling a boat is positioned nearby, contrasting with the natural surroundings. The sky is bright with scattered clouds, enhancing the scenic ambiance.
Cottage in Machiasport
4.98 out of 5 average rating, 232 reviews

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.

Top guest favourite
Cottage in Grand Manan
4.98 out of 5 average rating, 128 reviews

Element Four - Ember’s Edge

Keep it simple at this peaceful, very private, and centrally located island paradise. Located in the heart of the castalia marsh, a world known bird sanctuary, there is no shortage of wild life which is perfect for nature and bird lovers. Stunning views of the swallow tail lighthouse and the ferry coming and going from the island can be seen from the master bedroom upstairs or private backyard deck and patio. Short walk to beautiful beach. You will not be disappointed with this island gem.

Top guest favourite
A panoramic view captures the transitioning landscape of coastal Maine, where lush forests meet tranquil waters. The horizon is lined with gentle waves, and distant land forms are visible under a partly cloudy sky. The vibrant colors of the foliage create a serene atmosphere.
Cabin in Lubec
4.98 out of 5 average rating, 51 reviews

Rustic weathered hill top cabin

Welcome to our rustic cabin on a private dead end road over looking Quoddy Head and Gran Mannan . This open concept cabin offers two bedrooms sporting queen beds and a queen sleeper in the downstairs living room. Bedrooms located upstairs in an open loft. Although the cabin adjoins the homeowners cabin it has its own 60’ deck (with over 600 square feet of space) and private entrance. A wonderful space to relax, eat or refuel. 2 miles to Hamilton Cove 10 minutes to Roosevelt Campabello Park

Top guest favourite
The A-frame cabin is nestled among trees, surrounded by nature. An inviting view of Little Kennebec Bay is visible in the background, showcasing tranquil waters and coastal landscapes. The private deck with a hot tub extends from the cabin, offering a peaceful outdoor area.
Cabin in Machiasport
4.98 out of 5 average rating, 182 reviews

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

Guest favourite
The image presents a serene coastal view featuring calm waters surrounded by rocky shorelines. The distant landscape is dotted with a small village and lush green hills, under a sky filled with soft, white clouds.
Home in Cutler
4.95 out of 5 average rating, 61 reviews

Harbor View Cottage-quintessential fishing village

Our 150+ year old cottage, close to great views, restaurants and dining, the beach, outdoor activities (hiking, kayaking, Puffin and whale watching tours) and other family-friendly activities. You’ll love my place because of the views, the people, the ambiance, the outdoors space, and the quiet neighborhood. Our place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Just minutes from great ATV trails!…Inquire about our lobster fishing tours!

Top guest favourite
The exterior of a historic cape cottage is displayed, featuring a grey shingle facade with red doors. A well-kept lawn surrounds the property, and a blue sky is visible in the background, indicating a sunny day. Access to nearby natural scenery is suggested.
Cottage in Roque Bluffs
5 out of 5 average rating, 155 reviews

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!

Top guest favourite
A lakefront home features a spacious wooden deck that extends along the side, providing views of the water. Large windows offer ample natural light, while the surrounding grass creates an inviting outdoor space. The warm glow of sunset reflects off the exterior, enhancing the serene setting.
Cottage in Whiting
4.96 out of 5 average rating, 105 reviews

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.

Guest favourite
The image depicts a serene harbor scene with multiple fishing boats anchored on calm waters. A wooden pier extends into the water, bordered by green and natural surroundings. Sunlight reflects off the water's surface, creating a tranquil ambiance in the coastal setting.
Home in Cutler
4.95 out of 5 average rating, 21 reviews

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.

Top guest favourite
A geodesic dome is nestled among tall trees, surrounded by a natural landscape of pine needles and earth. A wooden deck extends from the dome, offering a seamless connection to the tranquil forest setting. The secluded environment creates a sense of privacy.
Dome in Bayside
4.98 out of 5 average rating, 129 reviews

The River Dome

Escape into nature with a stay in one of our luxury domes. Fully equipped kitchen with cookware, dishes, utensils, etc, as well as coffee and tea. Private bathroom with a toilet, shower, and essential toiletries. Two queen size beds with a loft space. The outdoor area includes a BBQ, private electric hot tub, and patio furniture. Kayaks are available during the summer months, as well as a communal fire pit. **Please note, there is a short walk down a hill to get to the dome**

Top guest favourite
An expansive view of a serene coastal landscape is captured, featuring a gently swaying field of tall grasses. The blue water glistens under clear skies, with trees dotting the horizon and a mist hovering over the distant shoreline.
Cottage in Machiasport
4.96 out of 5 average rating, 28 reviews

Oceanfront with Private Beach - Little Bay Retreat

Enjoy a relaxing retreat - peaceful oceanfront cottage with a private beach and easy access to the water. Savor the sights, sounds, and smell of the seaside in an Adirondack chair on the back deck. Dine peacefully in the oceanside gazebo. Appreciate the view of Long Point Nature Preserve across the bay. Explore the Bold Coast of Maine: The Bold Coast Trail, West Quoddy Headlight, Roque Bluffs, Jasper Beach, Lubec, and Campobello Island. Dine at the iconic Helen's Restaurant.

Guest favourite
A rustic log cabin is nestled among lush evergreens, featuring a deep red door that adds a touch of color. Adironack chairs and a picnic table provide seating on a gravel area. The serene setting is enhanced by the surrounding natural landscape.
Cabin in Cutler
4.86 out of 5 average rating, 14 reviews

The Cutler Cabin

Take it easy at this unique and tranquil getaway. You will love the location of this brand new off grid log cabin in the woods! Enjoy your stay on Maine's Bold Coast On this beautiful 20 acre property just 1/4 mile to a beach and the spectacular western head trail entrance. There are also many more undiscovered trails and small fishing villages in the area to explore. The cabin is very private and surrounded by forest. Easy check in and no cleaning fees!

Popular amenities for Cutler Harbor holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Washington County
  5. Cutler
  6. Cutler Harbor