Vacation rentals in Leonardville

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Top-rated vacation rentals in Leonardville

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of the contemporary waterfront home features a blue-grey facade and an array of large windows. A deck with seating overlooks the landscaped yard adorned with greenery and flowers, providing a welcoming entrance to the property. The surrounding trees enhance the natural atmosphere.
Home in Chamcook
4.99 out of 5 average rating, 104 reviews

The Shorebird - ocean views & beach - St Andrews

Enjoy panoramic ocean views from a contemporary waterfront home. Wake up with the sunrise over Passamaquoddy Bay (Bay of Fundy). Spend the day beach combing or just sitting on the deck and watching the tide. At night, get cozy with Netflix in our upstairs entertainment area or have an outdoor fire & star gaze. Drive 10 min to St. Andrews/35 min to New River Beach. Perfect for multiple couples, families, working remote, holiday gatherings or girls getaway (+ divers’ and bird watchers’ delight!).

Top guest favorite
The exterior of a modern two-story studio apartment is shown, featuring a private deck with a striped umbrella. Stairs lead up to the deck from the ground level, and the building is adorned with multiple windows and light gray siding.
Guest suite in Eastport
4.99 out of 5 average rating, 114 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 favorite
A white and wood-shingled cottage is displayed, featuring a clear sign that reads '1 EAGLE STREET.' The background reveals scenic ocean views, enhancing the peaceful setting with calm waters and distant pilings visible.
Home in Eastport
4.89 out of 5 average rating, 73 reviews

Eagles Bluff Cottage

Experience the natural beauty of Maine at Eagles Bluff Cottage, a fully furnished 2 bedroom 1 bath cottage with breathtaking ocean views in Eastport. Relax in the beautifully decorated living room, cook in the fully equipped kitchen, and sleep soundly in the comfortable bedrooms with fresh linens. The modern bathroom has all the amenities you need. Enjoy the peaceful and quiet surroundings from the patio. Book your stay today and experience the magic of Eastport! The home is dog friendly only!

Guest favorite
A view from a deck overlooking Holmes Bay, showcasing a grassy landscape with colorful foliage. A modern mini-home resembling a boat is positioned nearby, contrasting with the natural surroundings. The sky is bright with scattered clouds, enhancing the scenic ambiance.
Cottage in Machiasport
4.98 out of 5 average rating, 228 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.

Top guest favorite
The Carriage House is shown from outside, featuring a shingle facade and a double garage. A Canadian flag is raised beside the driveway, while a gravel path leads to the house surrounded by trees. A clear blue sky completes the serene setting.
Cottage in L'Etete
5 out of 5 average rating, 92 reviews

The Carriage House - Tranquility & Stunning View

Situated directly on the coastline of Passamaquoddy Bay, nestled within 28 acres, the Carriage House offers a unique opportunity for beach walks, relaxation, solace and stunning sunsets. You will have spectacular views of the Bay and across to St. Andrews and Ministers Island. Walk to our private beach and explore the beautiful coastline and experience dramatic Fundy tides (Up to 21ft between high/low water), or relax on the large deck watching bald eagles glide by. A birders paradise.

Top guest favorite
A private entrance is highlighted by a vibrant turquoise door, featuring a small window above the door handle. An outdoor patio area includes a bistro table with two chairs and a BBQ grill, surrounded by a modern black fence that enhances privacy.
Guest suite in St. Andrews
5 out of 5 average rating, 265 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!

Guest favorite
A rustic cabin features a bright red exterior with white accents, a front door adorned with nautical decor, and steps leading up to a covered porch. A rocking chair is positioned on the porch, offering a spot to relax. The surrounding landscape includes grassy areas and trees.
Place to stay in St. Stephen
4.97 out of 5 average rating, 188 reviews

Cozy Rustic Cabin w/Hot Tub

Our rustic cabin is the perfect space for those who want to enjoy a cozy, nature inspired getaway with quick access to St. Stephen, St. Andrews and the U.S border. Unwind in the bubbling hot tub after a day of exploring and then enjoy the beauty of a crackling fire, or cozy up inside and indulge in a movie marathon. "Our charming cabin accommodates up to 4 guests, with one queen-sized bed and a double pull-out sofa. We warmly welcome you to unwind and relax in our rustic, cozy cabin.

Top guest favorite
A geodesic dome is nestled among tall trees, surrounded by a natural landscape of pine needles and earth. A wooden deck extends from the dome, offering a seamless connection to the tranquil forest setting. The secluded environment creates a sense of privacy.
Dome in Bayside
4.98 out of 5 average rating, 120 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**

Guest favorite
A cozy living area features a brown sofa draped with a white blanket, accompanied by a wooden chair and a rocking chair. A small white coffee table is positioned in front, and light enters through two large windows, illuminating the hardwood floors adorned with an area rug.
Apartment in Lubec
4.88 out of 5 average rating, 171 reviews

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.

Top guest favorite
An aerial view captures a secluded property surrounded by water, with lush greenery framing the landscape. The winding road leads to the home, positioned on a small peninsula. Various tidal flats and islands are visible in the expansive blue water.
Home in Fairhaven
5 out of 5 average rating, 13 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.

Guest favorite
A sunlit sunroom features a cozy blue couch and two colorful chairs with striped cushions. A vibrant circular rug adds a lively touch to the space. A small green table holds various magazines, while large windows allow natural light to fill the room.
Home in Eastport
4.95 out of 5 average rating, 175 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 :)

Top guest favorite
Cottage in St. Andrews
4.98 out of 5 average rating, 168 reviews

Gull's Landing Guest Cottage

We are located in the heart of downtown St. Andrews, and free parking is provided for you. No need to drive anywhere! Everything is within walking distance. Whatever you are looking for, we have! Restaurants, pubs, pharmacy, grocery store, liquor store, boutiques, hardware store, recreational activities, whale watching, kayaking, bike tours, ghost tours, museums, kids activities, etc. The list goes on and on! Hope to see you this soon!

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