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

G$24,270 GYD per night

Guest favorite

Loft in Oak Haven, Canada

4.97 out of 5 average rating, 134 reviews

Safe Haven loft Waterfront with Kayaks, Oak Haven

Nice apartment on the scenic tidal Oak Bay. Sit & relax on lawn chairs & enjoy the view, watch the amazing tide change, walk on the ocean floor, explore the beach & go kayaking! Lovely space with open living/dining/kitchen area and Master Bedroom with Queen Bed and a small second bedroom w/2 twins! All new memory foam mattresses. Includes use of beach, canoes (2) kayaks (4) BBQ, fire pit w/wood, lawn chairs, coffee/tea, etc. NOTE: in May having some yard work done, price discounted to reflect.

Jan 3 – 10

G$17,987 GYD per night

Guest favorite

Cottage in Machiasport, Maine, US

4.97 out of 5 average rating, 156 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.

Mar 28 – Apr 4

G$45,625 GYD 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!

Oct 21 – 28

G$18,933 GYD 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 :)*

Sep 15 – 22

G$19,546 GYD 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 3 – 10

G$31,628 GYD per night

Guest favorite

Cottage in Machiasport, Maine, US

4.95 out of 5 average rating, 83 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.

Nov 30 – Dec 7

G$36,886 GYD per night

Guest favorite

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!

Jun 2 – 9

G$23,857 GYD 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.

Jun 7 – 14

G$19,914 GYD 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 6 – 13

G$36,003 GYD per night

Guest favorite

Guesthouse in Saint George, Canada

4.92 out of 5 average rating, 130 reviews

Riverview Guesthouse "The Loft"

Come and enjoy "The Loft",. Private back garden Oasis , private parking, high speed Wifi/ internet, Just a one minute walk to the riverfront with miles of groomed trails and boardwalks, One of the most prestigious neighbourhoods in the town. Minutes from the canal beach, this is a place where memories can be made. Year round rental

Dec 8 – 15

G$16,621 GYD 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

G$24,002 GYD per night