Vacation rentals in Cutler

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Top-rated vacation rentals in Cutler

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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, 115 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 an

Top guest favorite

A charming house presents a spacious front yard, enclosed by a white wooden fence. Lush green grass and trees offer a natural setting. A vehicle is parked nearby, and the tranquil environment is complemented by blooming flowers visible in the yard.

Guesthouse in Pembroke

4.98 out of 5 average rating, 196 reviews

Cobscook Bay Farmhouse on the Bay

One large bedroom with bath and beautiful water view. Key pad entry. The suite is a newly built totally private, extension on the house. You can walk across the field to the tidal marsh and onto the shingle beach. Guests, hike, bike and bird watch. 7 miles to a local restaurant and 13 miles into Eastport for whale watching, shopping and restaurants and cafes. Lubec is a 45 minute drive away. Your private entrance by keypad. The shared space is the front yard. Your driveway space is yours.

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, 216 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.

Guest favorite

A wooden swing set sits in a grassy area, overlooking a tranquil bay. Fishing boats can be seen in the water and a dock extends into the scene. Lush trees line the shore against a backdrop of blue skies and scattered clouds.

Tiny home in Lubec

4.86 out of 5 average rating, 44 reviews

Island views from The Sardine Shack at Globe Cove

Tucked away in Globe Cove, the last of the Sardine Shacks that housed the workers of Globe Canning waits for you. Views of the islands, views of the colorful working waterfront, an outdoor dining area, easy access to the shore to launch your own watercraft, close to West Quoddy and the Cobscook Shores trail system! Please note some blocked days are blocked for arrival only, due to limited cleaning staff, thus longer stays may be available that overlap the blocked days. More below, orJust ask!

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

5 out of 5 average rating, 35 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

Guest favorite

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, 58 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 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, 121 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!

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

4.95 out of 5 average rating, 76 reviews

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.

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

5 out of 5 average rating, 9 reviews

Cutler Harbor Bungalow

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

A cozy living area features a brown sofa draped with a white blanket, accompanied by a wooden chair and a rocking chair. A small white coffee table is positioned in front, and light enters through two large windows, illuminating the hardwood floors adorned with an area rug.

Apartment in Lubec

4.89 out of 5 average rating, 145 reviews

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.

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

4.95 out of 5 average rating, 86 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. Contact owner for monthly/winter stay discounts. 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.

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

4.7 out of 5 average rating, 23 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.