Vacation rentals in Cutler Harbor

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Top-rated vacation rentals in Cutler Harbor

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Guest favorite

Home in Jonesboro, Maine, US

4.96 out of 5 average rating, 104 reviews

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!

Jun 2 – 9

R2,231 ZAR per night

Guest favorite

Cottage in Machiasport, Maine, US

4.97 out of 5 average rating, 155 reviews

Cottage/w ocean view, hiking + lobster boat lounge

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 rooms 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.

Nov 22 – 29

R4,195 ZAR per night

Superhost

Tiny home in Oak Bay, Canada

4.84 out of 5 average rating, 316 reviews

Turning Tides Oceanfront Tiny Home

We at Turning Tides know that people are going through a lot right now. We want to encourage folks to: get out of their apartments, get out of the city, stay safe and sane somewhere you can have some space! Use our kayaks to enjoy the famous Bay of Fundy that’s located steps away. Or take in the tides from the back deck while you BBQ some dinner. Come have a fire! Sit and watch the entertaining animals we have. Come Enjoy! *WIFI IS SPOTTY! DOWNLOAD MOVIES IF YOU WANT THEM ON YOUR PHONE :)*

Jul 20 – 27

R1,756 ZAR per night

Guest favorite

Guest suite in St. Andrews, Canada

4.99 out of 5 average rating, 194 reviews

Homestead Cottage downtown Saint Andrews

This private newly renovated suite is perfect for 1-2 people looking to stay in the pretty seaside town of Saint Andrews. Situated away from the street, with ample parking, this suite has comfortable modern furnishings, a fully equipped kitchen and private bathroom, within a short walking distance to downtown Saint Andrews and its many amenities including restaurants, shopping, gardens, museums, walking routes, nature reserves, beaches as well as whaling and outdoor excursions. Come and stay!

Nov 13 – 20

R1,732 ZAR per night

Guest favorite

Cabin in East Machias, Maine, US

5.0 out of 5 average rating, 10 reviews

Mountain Cabin with a View in East Machias, Maine

Our newly constructed cabin is located on a secluded mountain in East Machias, Maine. This small cabin has incredible views of the East Machias River from the front porch. Opened in September of 2023, be one of our first guests to stay in Chickadee Cabin and enjoy sounds of local birds, watch the eagles soar overhead, the deer frolic through the trees, and wild turkeys that inhabit this wooded area. The cabin is constructed of lumber milled from the property. Our cozy cabin sleeps 4-5.

Jun 10 – 17

R2,695 ZAR per night

Superhost

Loft in Grand Manan, Canada

4.88 out of 5 average rating, 137 reviews

Souwest Sunrise

Idyllic GRAND MANAN ISLAND OCEANFRONT LOCATION! The first thing you`ll notice as you embark down the winding driveway is the fresh sea breeze and the sound of the waves crashing against the rocky shore. This oceanfront property is located at the peaceful end of the island, well known for it`s serenity. The loft offers panoramic views of the Bay of Fundy and beyond. The beautiful loft compromises a queen size bed, kitchenette, shower, and a peaceful seating area overlooking the bay.

Jun 8 – 15

R2,894 ZAR per night

Guest favorite

Cabin in Robbinston, Maine, US

4.94 out of 5 average rating, 174 reviews

Oceanfront Cliff Cabin Camelot

Ever dreamed of finding private seaside solitude on the rocky Maine coast? Camelot sits upon an isolated thirty-foot cliff overlooking the Atlantic. At high tide, waves crash against the sandstone rocks. At low tide, a hundred feet of beach is revealed for shell collecting, clam digging and rock skipping. With no roads within a half mile, you might not see another soul during your stay. Enjoy peaceful off-grid cabin life. Campfire cookouts, stunning views, and cozy beds.

Sep 4 – 9

R3,068 ZAR per night

Guest favorite

Cottage in Machiasport, Maine, US

4.95 out of 5 average rating, 81 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.

Oct 24 – 31

R3,282 ZAR per night

Superhost

Apartment in East Machias, Maine, US

5.0 out of 5 average rating, 14 reviews

Luxury Studio at the Downeast Retreat

This private and cozy apartment offers a modern appeal and a spacious bathroom for a luxurious hotel-style stay! With plenty of parking space for your ATVs and easy access to the Down East Sunrise Trail, this is a perfect destination for anyone looking to find adventure. Take a look at my guidebook for all the food, shops, and sights that locals and travelers alike have grown to love and revisit. I hope to host you soon!

May 26 – Jun 2

R2,233 ZAR per night

Guest favorite

Cabin in Roque Bluffs, Maine, US

4.9 out of 5 average rating, 217 reviews

Elva P. Cabin at Welch Farm

Drink your morning coffee as you walk the farm's picturesque blueberry fields and shoreline. At night, enjoy sitting around a cozy campfire toasting marshmallows. As you enjoy the scent of fir trees, salt air, and the unspoiled beauty of Downeast Maine, Relax. Spend several days with us exploring the farm or as a home base to venture to other locations around Downeast Maine and Canada.

Mar 12 – 19

R1,772 ZAR per night

Guest favorite

Cottage in Whiting, Maine, US

5.0 out of 5 average rating, 25 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.

May 16 – 23

R3,310 ZAR per night

Guest favorite

Cottage in Roque Bluffs, Maine, US

4.97 out of 5 average rating, 171 reviews

Ellie's Cottage—lovely, bright, and tasteful

This sweet little cottage has amazing light and views across fields and woods into the ocean. Sunrises are spectacular and stargazing at night is awe-inspiring. Perfect for a quiet getaway where you can really unplug. The State Park is just 2 miles away. Roque Bluffs is a special place in the world with much to explore.

Oct 18 – 25

R2,554 ZAR per night