Holiday houses in Leonardville

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Top-rated holiday rentals in Leonardville

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Top Guest favourite
The exterior of Chadbourne House is illuminated at night, showcasing its welcoming architecture. A decorative sign identifies the property, surrounded by well-maintained landscaping and soft lighting. The deck is visible on the upper level, adding to the inviting ambiance of the setting.
Guest suite in Eastport
4.99 out of 5 average rating, 119 reviews

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.

Guest favourite
The Periwinkle Cottage is illuminated by charming outdoor lights, framed by lush trees. A Canadian flag flutters beside a sign indicating the cottage name. A scenic view of the water and sunset is visible in the background, with a lighthouse standing nearby.
Cottage in Wilsons Beach
4.85 out of 5 average rating, 55 reviews

PERIWINKLE COTTAGE BY THE SEA-PRIVATE AND COZY

NEW MASTER BEDROOM OVERLOOKING OCEAN AND NEW AND LARGER SCREENED IN PORCH ADDED IN 2023. NOW 3 BR COTTAGE W/LOFT The charming Periwinkle cottage overlooks ocean, great views of sunsets, whales, eagles, seals/boats pass by.2021 Major reno w/ enlarged cottage, new kitchen, bathroom, large deck, loft area added. The screened porch leads to large open deck. Chairs overlooks the water with a small firepit. Cottage sleeps 6 with loveseat in LR making a twin bed. Loft has small bed for kids

Superhost
Tiny home in Eastport
4.82 out of 5 average rating, 129 reviews

Immaculate tiny house,walk to everything Eastport!

This is a new tiny house, walk to everything.The oceans at the bottom of the hill! Quick walk to the public beach access, and everything else Eastport has to offer.You can be anywhere in town in 5 minutes but located on a quiet street.Such a quaint New England town.You will love this place.Cozy, comfy, has everything you need and then some!Full size shower and tub, big where it counts! Well appointed, nice finishes and linens.Great for a quick visit or an extended stay, you'll love it!Historic

Guest favourite
A pair of yellow wicker chairs is positioned on a wooden deck, overlooking a calm bay at sunset. The sky displays soft hues of orange and pink, reflecting on the water. Lush greenery frames the view, enhancing the tranquil setting.
Home in Wilsons Beach
4.89 out of 5 average rating, 35 reviews

Oceanside Oasis

Forget your worries as you relax and watch the spectacular sunsets in the oceanside home. This property overlooks the beautiful bay of Fundy with spectacular views of sunsets. Morning coffee in hand, enjoy the tide come in as fishing boats go out, watch seals play, and listen to the foghorn and seagulls right from the deck. Bike/hiking trails, 2 beautiful lighthouses and Roosevelt Park are all within 8 kms. Small convenience store, restaurant and fishing pier are all within walking distance.

Top Guest favourite
A charming lakeside cottage is framed by lush greenery, showcasing a large deck with seating. Expansive windows reflect the serene waters of the lake, creating a harmonious connection between nature and the retreat.
Cottage in Moores Mills
5 out of 5 average rating, 174 reviews

Love The Cottage/King beds/Hot tub under the stars

Escape to an enchanting cottage retreat, nestled on the shores of Moores Mills lake. Immerse yourself in the serene beauty of nature as you soak in the hot tub and gaze out over the tranquil waters. Everything you need to make beautiful memories! #cozycanadiancottage ✅ Swimming, Kayaking ✅ Fishing, Pedal boating ✅ Arcade Pac-Man, Record Player w/ 45’s ✅ Bonfire pit - free firewood ✅ Outdoor BBQ ✅ Sleeps 6: 2 King, 1 Queen bed ✅ 51 inch Smart Roku TV ✅ Amazon Prime, Roku ✅ Screened inporch

Top Guest favourite
A large, arched window provides a stunning view of the bay, allowing natural light to fill the space. Nearby, a ceiling fan enhances air circulation. Scenic water views are visible, along with trees lining the waterfront.
Place to stay in Eastport
5 out of 5 average rating, 35 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!

Top Guest favourite
A spacious wooden deck offers panoramic views of the surrounding landscape and water. Outdoor seating is provided with a round dining table at the center, surrounded by several chairs. A lounge area with cushioned seating is visible, inviting relaxation in the open air.
Cabin in Lubec
4.98 out of 5 average rating, 51 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

Top Guest favourite
The exterior of a newly renovated suite is visible, featuring a light-colored facade with multiple windows. A modern black fence encloses a private area beside the entrance, which is complemented by a gravel pathway and lush greenery in the surrounding landscape.
Guest suite in St. Andrews
5 out of 5 average rating, 270 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!

Top Guest favourite
An outdoor private electric hot tub is surrounded by wooden fencing and dimly lit by string lights. The setting offers a tranquil atmosphere with pine trees visible, and wooden decking provides access to the tub. Soft blue lighting illuminates the interior water.
Dome in Bayside
4.98 out of 5 average rating, 131 reviews

The River Dome

Escape into nature with a stay in one of our luxury domes. Fully equipped kitchen with cookware, dishes, utensils, etc, as well as coffee and tea. Private bathroom with a toilet, shower, and essential toiletries. Two queen size beds with a loft space. The outdoor area includes a BBQ, private electric hot tub, and patio furniture. Kayaks are available during the summer months, as well as a communal fire pit. **Please note, there is a short walk down a hill to get to the dome**

Top Guest favourite
Home in Fairhaven
5 out of 5 average rating, 21 reviews

Birch Point Retreat

Experience island living with all the comforts of home in this modern cottage finished in 2025. Wake up in your king size bed to a different view every morning as the tide transforms the landscape from the ocean floor to a 30-foot deep harbour. Watch the wildlife put on amazing shows while you relax or bbq on the wraparound deck. Catch the sunset from huge picture windows or soak in the tub after a long day exploring the acres of private land that surround you.

Top Guest favourite
Guesthouse in Pembroke
4.99 out of 5 average rating, 211 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 to the beach and to local trails. Hike, clam, birdwatch, bike, sit and read.... There are several restaurants in or near Pembroke. It is 13 miles to Eastport for whale watching, shopping, restaurants and cafes. Lubec is a 45 minute drive away. Your private entrance by keypad. Your driveway space is yours.

Top Guest favourite
An outdoor hot tub with steps leads to a doorway offering visibility into a well-lit interior space. The tub is illuminated in purple tones, creating a relaxing ambiance. A window and shaded lighting are visible, enhancing the inviting outdoor area.
Home in Eastport
4.95 out of 5 average rating, 194 reviews

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 :)

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