Vacation rentals in Cutler Harbor

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Top-rated vacation rentals in Cutler Harbor

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Top guest favorite

Home in Cutler

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.

5.0 out of 5 average rating, 19 reviews

Top guest favorite

A comfortable outdoor seating area features light-colored cushions on a sectional sofa, complemented by a round coffee table. A dining table is visible in the background, with lush greenery and serene ocean views enhancing the scenic atmosphere.

Home in Addison

Oceanfront Home on 5 Acres w/ Private Beach & Cove

Beautiful coastal home feet from ocean with 1500 ft of water frontage with 180 views & private beach for picnics, canoeing & water sports. Located on 5.2 acres with large wrap-around porch, there's plenty of privacy for family get-aways and outdoor dining. Remodeled kitchen with all new appliances and entire home freshly painted and upgraded. Drink coffee on the large wrap-around porch while watching lobster boats. Visit National Acadia Park, Bar Harbor, Winter Harbor & many towns in between.

4.93 out of 5 average rating, 137 reviews

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

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

4.98 out of 5 average rating, 228 reviews

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

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.

4.95 out of 5 average rating, 104 reviews

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

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!

5.0 out of 5 average rating, 171 reviews

Guest favorite

The cottage sits beside a calm river, surrounded by vibrant autumn foliage. Red and orange leaves reflect on the water's surface, creating a serene scene. The quaint structure features large windows, allowing for natural light to illuminate the interior.

Cottage in Whiting

Little Green Cottage

The Little Green Cottage is a peaceful location, on the edge of a calm river, where you can frequently see turtles and frogs. Truly a place to see the night sky and experience nature. Acadia is a little over 2 hours away. Quoddy Head State Park and Campobello Island (Canada - bring your passport), is within 30 minutes. Take a break and unwind at this peaceful oasis. We just added an office shed for those who have to work on vacation. Additional fee to rent so please request in the booking.

4.93 out of 5 average rating, 116 reviews

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

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.

4.97 out of 5 average rating, 119 reviews

Top 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

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.

4.97 out of 5 average rating, 36 reviews

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

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.

4.93 out of 5 average rating, 229 reviews

Superhost

The shoreline is visible with clear water in the foreground and a mix of cottages lining the coast. Lush greenery and bushes add vibrant color, while a cloudy blue sky stretches above, creating a serene coastal scene.

Cottage in Cutler

Harborside cottage with unequaled maritime views

Small cottage with tremendous view of Cutler Harbor right from the center of it. Best seat in town. The cottage was the town store for generations and it retains some of the rustic elements of the store from a renovation years ago. It is great spot for hiking base camp or staying right there for great harbor views. The building is located close to the road, but traffic is usually very low. Parking in back and some lawn for outdoor activities.

4.78 out of 5 average rating, 40 reviews

Top guest favorite

A stone pathway leads to the entrance of a log home, surrounded by trees and offering views of the tidal river in the background. The sky is partly cloudy, with patches of blue visible.

Cottage in Machiasport

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.

4.96 out of 5 average rating, 177 reviews

Top guest favorite

A geodesic dome structure is visible, featuring large glass panels that reflect natural light. In front, seating is arranged near a fire pit, and a hot tub is positioned nearby. Lush greenery surrounds the area, contributing to a serene outdoor setting.

Dome in Grand Manan

Geodome water view stay on Grand Manan Island

Situated on picturesque Grand Manan Island, this geodesic dome has a beautiful view the ocean. You can see Swallowtail Lighthouse and the Grand Manan Ferry as it comes and goes. This new stay has two queen beds, one on the first floor and one in the loft. Equipped with a full kitchen, bathroom, deck, lawn, fire pit and hot tub. Visit Grand Manan Island and stay in our luxurious dome!

4.99 out of 5 average rating, 221 reviews