Vacation rentals in Cutler Harbor

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Top-rated vacation rentals in Cutler Harbor

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Top guest favorite
The exterior of the property is illuminated at night, showcasing a three-story structure with large windows and an inviting deck. Stairs lead to the second level, while the grassy area surrounds the house, creating a natural setting.
Home in Whiting
5 out of 5 average rating, 23 reviews

On The Fly Inn Downeast Maine

Where relaxation begins & memories are made. Abandon the hustle & bustle to reconnect with nature, family & friends. This stunning 4 season lake escape is nestled on a private sand beach on Garnder Lake. Explore Downeast's bold coast, vast stretches of woods, rivers, streams & beaches. Watch wildlife from the porch with coffee or roast the perfect s'more over the campfire by the beach. Enjoy fishing, lazy summer lake days, hunting, leaf peeping or as a winter base camp. Welcome to On the Fly Inn

Top guest favorite
A charming two-story cottage is seen down a gravel path, surrounded by greenery and trees. The exterior features wooden shingles, a small deck with sliding glass doors, and a grassy yard that extends towards a serene landscape.
Cottage in Grand Manan
4.97 out of 5 average rating, 114 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 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
4.99 out of 5 average rating, 140 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

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, 149 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, 92 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 spacious wooden deck overlooks the ocean, framed by tall trees swaying in the breeze. The stunning view captures the vibrant blue water against a clear sky, inviting a peaceful retreat outdoors.
Cottage in Beals
5 out of 5 average rating, 43 reviews

Oceanfront Island: Hiker & Honeymooner’s Paradise

You can’t get any closer to the ocean! This is special. This is where artists are inspired. If you love nature and need quiet, calm and anonymity, look no further. The sunsets are unrivaled. Hike the preserve. Stare at the ever-changing ocean. Lobster boats come right up close to our pink granite, deep water frontage. No mudflats here. Floor -to -ceiling glass in the cozy cottage gives the illusion of being on a boat. Easy access to the island by bridge. Come breathe!

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.

Top guest favorite
A modern log cabin is set amidst a clearing, surrounded by tall trees. A stone patio with seating is visible, complemented by natural rocky formations and open grassy areas. The cabin's exterior features a dark wood finish, with a welcoming porch extending from the front.
Cabin in Gouldsboro
4.99 out of 5 average rating, 192 reviews

40 Acre Wooded Paradise w/ Firepit Near Acadia

🌲 Welcome To Rocky Roods Cabin 🌲 Nestled In A Clearing and Surrounded By Woods, You'll Find Our Serene & Modern Log Cabin Awaiting Your Adventurous Spirit. Experience 40 Acres Of Privacy w/ On-Site Hiking Trails , Deeded Beach Access and Land Untouched By Light Pollution Where The Night Sky Shines Bright Around Your Own Wood-Burning Outdoor Firepit! 🎅 Ho, Ho Ho...Tis The Season 🎅 Rocky Woods Cabin Will Be Decorated For The Holidays Through December!

Top guest favorite
Aerial view of a waterfront cabin surrounded by lush greenery, showcasing a mix of trees and rocky shoreline. The calm waters of the bay reflect the soft colors of the sky, creating a tranquil scene. The cabin is positioned uniquely near the water's edge.
Home in Steuben
5 out of 5 average rating, 22 reviews

Luxury Oceanfront Cabin w/ Sauna by Acadia

Wake up to the sound of lobster boats and unwind by the fire as seals play in the bay. This brand-new waterfront cabin offers stunning ocean views and modern comforts, just 10 minutes from Winter Harbor and a quick ferry ride to Bar Harbor. Enjoy hiking, boat tours, fresh lobster, and easy access to Acadia’s Schoodic Peninsula. Designed for both adventure and relaxation — the ultimate Maine coastal escape. Images taken by @dirtandglass and @heypamcakes

Top guest favorite
Two white Adirondack chairs are positioned near a fire pit on a pebbled beach, surrounded by lush green grass and yellow wildflowers. Calm waters extend into the distance, framed by a tree-covered shoreline under a cloudy sky.
Cottage in Machiasport
4.98 out of 5 average rating, 41 reviews

Oceanside cottage in remote location. Cottage 2

Relax with the whole family at this peaceful place to stay. Off the beaten path and accessible by car two hours before and two hours after low tide. Beach combing and birdwatching. Kids will love catching crabs and skipping rocks. The serene atmosphere is unmatched and the stars at night are worth the trip. It’s an adventure in relaxation. Take time to slow down and escape the hustle and bustle. No traffic noise, just wind, waves, birds, and serenity.

Superhost
A calm body of water reflects the clear blue sky and surrounding greenery. The shoreline is lined with patches of grass and forest, leading to more distant trees. Gentle curves in the landscape guide the eye towards the horizon.
Cottage in Cutler
4.77 out of 5 average rating, 30 reviews

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.

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
4.95 out of 5 average rating, 150 reviews

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.

Popular amenities for Cutler Harbor vacation rentals

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