Vacation rentals in Cutler

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Top-rated vacation rentals in Cutler

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Guest favorite
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 favorite
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, 233 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 favorite
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 favorite
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, 188 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 favorite
A charming farmhouse is set against a backdrop of lush greenery. The structure features a welcoming entrance with an orange door, complemented by bright windows. Flowering plants in the foreground add a touch of color to the serene landscape that leads to the horizon.
Farm stay in Lubec
4.89 out of 5 average rating, 157 reviews

SPECTACULAR SEASIDE FARMHOUSE

Located in the most eastern town in the US, sits a rustic 1800 farmhouse overlooking the quaint seaside village of Lubec, Maine. This 4 bedroom, 2 bath rental sleeps 8 comfortably and has breathtaking views of the colorful fishing harbor, Canada's Campobello Island, and the famous Moholland Lighthouse. The cottage is immaculate with all amenities and is fully stocked. Enjoy your coffee while you watch the sunrise from your back deck as the local lobstermen get ready to haul their traps.

Top guest favorite
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, 158 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 favorite
Aerial view showcasing the cabin nestled among lush green trees along the coastline. The serene waters of Holmes Bay reflect the sky, with a sandy beach visible in the distance. The surrounding landscape offers a mix of wooded areas and open spaces.
Cabin in Cutler
4.96 out of 5 average rating, 101 reviews

Bear Beach Maine! Sandy Beach, Sunsets & Sauna

Welcome to Bear Beach Maine, your private oceanfront paradise. If you are looking for a cozy, spacious and extremely well-appointed home nestled peacefully in the woods and directly on a secluded, sandy beach this is your place! From the moment you walk through the door you will feel warmly greeted by this cedar log home. The open concept with cathedral ceiling, large field-stone fireplace and comfy furnishings are equally favorable for both larger gatherings and intimate parties of two.

Top guest favorite
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.

Top guest favorite
An aerial view of a red one-room mini home set against a backdrop of lush greenery and a serene lake. The exterior features a gravel area with large rocks and a seating arrangement, providing a tranquil outdoor space for relaxation.
Tiny home in Whiting
4.98 out of 5 average rating, 47 reviews

Little Mountain Cottage in Whiting Maine.

Relax at this peaceful private mountain top minihome. 190 feet of elevation with panoramic views of Orange and Rocky Lakes. Awesome sunrises and sunsets. Nearby boat landing. Fishing winter and summer. 1.5 miles off of Rt. 1. 12 miles to Dunkin Donuts, grocery store, Helen’s famous blueberry pie and many other services. Hunters and fishermen welcome. Near 4 wheeler trails. Nice breezes. Great place to walk and hike as well as many trails throughout Washington County. Abundant wildlife.

Top guest favorite
A charming white cottage is positioned beside a calm body of water, framed by tall, green trees. In the background, a rainbow arcs gracefully across the sky, adding a touch of color to the serene landscape.
Cottage in Machiasport
5 out of 5 average rating, 42 reviews

Remote Oceanside cottage (closer to water) #1

Off the beaten path. Escape the sound of traffic and listen to the waves outside your window. This location is an adventure and is accessible by car at low tide and by canoe at high tide. Kids will love beach combing while the adults enjoy relaxing on the shore. There’s also a gazebo beside the spring fed frog pond. Deer graze on the grass in the morning. If you are a bird watcher you can see the sea birds and eagles. The location is perfect for those who want to escape from it all.

Guest favorite
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.

Guest favorite
The historic Station House showcases a classic two-and-a-half-story design, with a striking red roof and white clapboard siding. Large windows allow natural light to fill the interior, while a welcoming green door serves as the main entrance. A smaller structure is visible to the left.
Home in Lubec
4.92 out of 5 average rating, 213 reviews

The Station house at West Quoddy Station

The Station House, c1915, formerly USCG Station Quoddy Head from 1915-1970 and currently is an adaptive lodging reuse. On TheNational Register of Historic Places, The Station House has 5 bedrooms, 2 1/2 baths, sleeping 9 comfortably. The SH is located 1/2 mile from West Quoddy Head State Park, the Easternmost Point in the US. You will experience peaceful beauty, amazing sunrises and sunsets over the ocean, 2 lighthouses, with views of Lubec, Eastport and Campobello.

Popular amenities for Cutler vacation rentals

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