Vacation rentals in Cutler Harbor

4.94 out of 5 average rating, 133 reviews

Home in Jonesboro

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

4.99 out of 5 average rating, 102 reviews

Cabin in Machiasport

A-Frame with 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

4.98 out of 5 average rating, 185 reviews

Guesthouse in Pembroke

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.

4.95 out of 5 average rating, 56 reviews

Home in Cutler

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. A short 15-25min ride to restaurants and groceries, located in neighboring towns.

4.92 out of 5 average rating, 106 reviews

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.

4.98 out of 5 average rating, 208 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.

5 out of 5 average rating, 113 reviews

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!

4.97 out of 5 average rating, 37 reviews

Tiny home in Whiting

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.

4.94 out of 5 average rating, 62 reviews

Campsite in Machiasport

Glamping at Bucks Harbor Maine

Beautiful, private, fully outfitted, waterside Glamping. Furnished Bell tent with all amenities including queen sized bed, picnic area,fire pit and water views. Just a short 1/4 mile hike in from free parking area. A short drive to Machias and surroundings. Close to Jasper Beach. Toilet tent and camp shower provided as well as camp stove. Place settings and picnic table, camp coffee pot provided. Bring your boat or bike. Launch your kayak at high tide right from the campsite. Enjoy.

Superhost

Place to stay in Grand Manan

4.86 out of 5 average rating, 22 reviews

Oceanside Grand Manansion

Welcome to The Grand Manansion! This gorgeous water front cottage with a castle like turret offering spectacular views of the Bay of Fundy is the perfect destination for your Grand Manan vacation. The Manansion is hidden from the main road in Deep Cove giving it a private atmosphere while you take in the 180 degree views during your unplugged stay. Outside of the home offers multiple oceanside decks as well a large open yard. ** Stay tuned, more photos coming soon!!

Superhost

Cottage in Cutler

4.71 out of 5 average rating, 21 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.

4.94 out of 5 average rating, 126 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.

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Other great vacation rentals in Cutler Harbor

Loft in Grand Manan

4.87 out of 5 average rating, 144 reviews

Souwest Sunrise

MelissaRating, 5 stars10 months ago

This is a wonderful retreat in a spruce forest on the cliffs at the south end of the island. The loft is open yet cozy with a well supplied kitchenette, small bathroom, comfy linens, multiple places to sit and soak up the sound of the surf. There is easy access to a walking trail that traverses the front of the property that winds along the cliffs through the forest to the heath. Good wireless connection available but a great place to be unplugged.

Home in Cutler

5 out of 5 average rating, 3 reviews

Beautiful Cutler Harbor Home

VictoriaRating, 5 stars3 weeks ago

This is our crew second time staying at this property in the last month and once again Lucas was super responsive and helpful. He made sure we had everything we need ahead of time. The house was clean and clutter free when we arrived. The view on the front porch is breath taking and so peaceful in the early mornings and late nights, perfect after a long day of work. Our team needed to stay another week in Machias area, so we once again booked with Lucas but at his neighboring property and really looking forward to it.

Superhost

4.87 out of 5 average rating, 83 reviews

Frisky Fish Cottage on the water

DeanneRating, 5 stars6 months ago

I absolutely loved this cottage. It was cozy and inviting. Great location. The host Lydia was attentive and always ready and available to answer questions. I am planning to return soon.

4.91 out of 5 average rating, 32 reviews

Farm stay in Cherryfield

Farm Stay on a River Close to Acadia, Yoga, Swim

NatalieRating, 5 stars6 days ago

We absolutely loved staying at the Root to Rise farm! It was such an adorable little space and perfect for our trip! This was our 3rd stop on an east coast road trip and Gina was an awesome host! Her property is absolutely gorgeous and she was incredibly responsive and helpful with recommendations for local spots! I wish we would have had a little more time to explore the property more because it was stunning. The home is incredibly well kept and adorable inside. Would definitely return and recommend to anyone traveling through the area!

4.97 out of 5 average rating, 33 reviews

Seaclusion: Ocean-front home on Maine’s Bold Coast

SarahRating, 5 stars2 weeks ago

A great place to weather a storm! We were greeted by a rare nor’easter so we weren’t able to hike around much but we enjoyed having coffee and looking out the windows at the gorgeous view. There was a bit of a snafu with the cleaners that take care of the property, but Brian was very responsive and apologetic and offered multiple solutions. The bidet in the bathroom downstairs was a bonus!

Cabin in Roque Bluffs

4.86 out of 5 average rating, 251 reviews

Elva P. Cabin at Welch Farm

BrianRating, 5 stars3 weeks ago

Beautiful, private surroundings. We needed a break away from noise and traffic and this was the perfect spot. We'd return for sure.