Holiday rentals in Eastport

5 out of 5 average rating, 54 reviews

Historic Bayside Corthell & Gardner Building

The historic Corthell & Gardner building overlooks Passamaquoddy Bay, the island of Campobello and Eastport's working waterfront. The Crow's Nest is an 1150 SF loft, embracing the building's history and designed for comfort. Watch for whales, seabirds, harbor seals and our lobster fleet from the privacy of your own deck. Run downstairs for a craft beer at Horn Run Brewing or a great glass of wine at Phoenix Fine Wines. Perfect for artists, writers and couples looking for a romantic getaway.

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

Guest house 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.

4.99 out of 5 average rating, 88 reviews

Guest suite in Eastport

Studio @ Chadbourne House: Private deck and more!

Modern studio apartment in a historic building in Eastport Maine. 460 sq ft with private deck, king-sized bed, sitting area w/gas stove, galley kitchen, and bathroom. Walk-out second story deck overlooks large side-yard and has table, umbrella, and chairs for outside dining or simply enjoying the day. Private entrance and off-street parking. Well-equipped kitchen w/ refrigerator/freezer, Keurig, kettle, toaster oven, cookware, knives, utensils, dinnerware. Large closet with vacuum and heater.

4.98 out of 5 average rating, 208 reviews

Cottage in Machiasport

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.

Place to stay in Eastport

5 out of 5 average rating, 13 reviews

The Salty Seagull

Enjoy a stylish experience at the Salty Seagull! After 8 months of extensive restoration and preservation efforts, this centrally located, fully furnished NEW 1-bedroom loft is now available. All furnishing and accessories throughout have been recently purchased. Relax by the restored grand window with the most breathtaking views of the bay in Eastport. Watch as whales pass by, or fisherman leave the working waterfront as the sun rises. Walking distance to all downtown galleries and eateries!

4.91 out of 5 average rating, 82 reviews

"Jolly Breeze" New apartment. Deep cleaned!

Updated Granny Suite apartment in quiet location and still walking distance to downtown. Large back deck over looking a private forest on a hill that leads down to the water. (Water view peaking around the trees). One bedroom, quality latex foam queen mattress with added 3" memory foam topper. Double pine futon with thick mattress for additional guests. Garage space for bikes. Washer/dryer. High speed internet, Internet capable large screen TV, DVD player. Wood, stone and slate.

5 out of 5 average rating, 39 reviews

Loft in Eastport

Modern Loft on The Waterfront

Welcome to Eastport, the most eastern city in the United States. And welcome to The Harbor house. I hope you enjoy it as much as we have. Our loft is located on the waterfront, above an old brick storefront. It’s tastefully furnished with a modern twist, with five large windows overlooking the water that also creates a very comfortable atmosphere. As the sun rises over Campobello each morning, it fills the Harbor House with its morning light. Be prepared to want to come again.

4.89 out of 5 average rating, 144 reviews

Flat in Lubec

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.

4.95 out of 5 average rating, 157 reviews

Home in Eastport

Mermaid's Mini Mansion

With peak ocean views as well as the first sunrise in the nation from our location across from Todd's Head, the mini-mansion offers a full kitchen, comfortable bedroom, outdoor 3 person hot tub, washer dryer, yard and ocean breezes. Strolling distance to the pier for a whale watch, the artistic downtown, and the brewery! There is a Weber grill, outdoor seating, bikes to use, books, games, record player and WIFI. We welcome your pets and your children :)

5 out of 5 average rating, 21 reviews

Home in Eastport

Shackford Cove Cottage

New cottage that opened in 2024!! Shackford Cove Cottage is a charming cottage with the best view of Shackford Cove in Eastport! It features a relaxing entertaining space on the first floor and two bedrooms and a bath on the second. It was built as a sardine workers' housing dating to the turn of the last century. Converted to a vacation home thirty years ago, it was just updated to make a comfortable vacation home for your stay.

5 out of 5 average rating, 51 reviews

Loft in Eastport

The Waterfront Loft Eastport

One of the best views on the island! The 2nd floor of this historic, waterfront Eastport building is a rustic loft in the heart of downtown Eastport. Built in 1863, the space has been fully renovated with a modern & industrial vibe. Includes expansive views of Passamaquoddy Bay (including occasional whale, seal, and porpoise sightings!), Campobello Island, working lobster and scallop boats, and historic downtown Eastport.

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Other great holiday rentals in Eastport

Cabin in Eastport

4.71 out of 5 average rating, 24 reviews

Peaceful Oceanfront Cabin

MargaretRating, 5 stars9 months ago

The cabin is great! The scenery is beautiful. We spent most of our time out on the deck watching for seals and enjoying the birds. We only had a few questions about the cabin and John responded quickly and in a friendly fashion. I felt the description of the cabin matched the reality. It was a great place to unwind. We hope to stay there again.

4.87 out of 5 average rating, 121 reviews

Home in Robbinston

Coastal Cottage, Downeast Maine. May-Oct.

DavidRating, 5 stars1 month ago

Stayed while in the area for work. Quiet and met expectations.

5 out of 5 average rating, 10 reviews

Cabin in Eastport

Oceanfront escape with pool access - 2 Bdrm

ChristoRating, 5 stars9 months ago

We booked this space for my parents from South Africa and they had a delightful stay at Eastport. The hospitality from our host,Janet, enhanced our experience. She went out of her way to make us feel at home and we could not wish for a more attentative host. The unit was pristine clean and beautiful and we enjoyed the peaceful surroundings. Janet- thank you for taking care of us in the way you did.

4.95 out of 5 average rating, 61 reviews

Cottage in Wilsons Beach

Whale of a View Oceanfront Cottage! Amazing views!

NancyRating, 5 stars7 months ago

We had a terrific, peaceful and relaxing time at Whale of a View! The house was comfortable, clean and had a wonderful view of the water and we appreciated all the different sitting options. Screened porch, beautiful deck, picnic table and around an outdoor fire pit. Beds and furniture were comfortable, kitchen clean and had all the utensils/appliances that we needed. Campobello Island has a lot of different places to explore, hike, and soak in the beauty.

4.91 out of 5 average rating, 98 reviews

On Eastport Harbor Apartment

AndrewRating, 5 stars12 months ago

Great place, super, clean, great communications and directions, wonderful view, convenient to ALL of Downtown Eastport

Shipping container in Saint Stephen Parish

4.94 out of 5 average rating, 34 reviews

The Hilltop Hideaway | Lake-view w/ hot tub

TerryRating, 5 stars1 week ago

When we first entered the property it was the perfect little hideaway. Peaceful and quiet was what we were looking for and this place gave us all that. Sitting on the dock and making s'mores at the fire pit was so relaxing. Evenings and mornings surrounded by the landscaping hade amazing views. Waking up in a comfortable bed watching the sunrise behind all the glass was another amazing scene. To be honest there were so many amazing things about this rental that I could go on and on. We will definitely be back to enjoy the kayaking on the lake and beautiful atmosphere. Was one of my favorite places to be. Thank you again Gordon for providing such a great getaway.

Tiny home in Eastport

4.83 out of 5 average rating, 107 reviews

Immaculate tiny house,walk to everything Eastport!

JulieRating, 5 stars3 months ago

What a wonderful little house! So easy to access. It's walking distance to the main drag so you can easily get around. It was extremely quiet. Everything was in good order, very clean and tidy. Marybeth had wonderful little personal touches that I really appreciated. Like ramen and Bevita cookies. Some soft drinks in the fridge. Coffee on hand. What a delightful little town and and what perfect space.