Guesthouse vacation rentals in Penobscot River

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Top-rated guesthouse rentals in Penobscot River

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Guest favorite
A bright and airy living space features cathedral ceilings and large windows overlooking the surrounding woods. A cozy seating area is arranged with two chairs and a small table, complemented by a comfortable sofa. Warm wood floors add to the inviting atmosphere.
Guesthouse in Appleton
4.94 out of 5 average rating, 412 reviews

BRAEBURN at The Appleton Retreat

The Appleton Retreat is a short scenic drive to Belfast, Camden and Rockland. Braeburn at The Appleton Retreat is down a 1/2 mile driveway, on 120 acres of private land, bordered by a 1,300 acre Nature Conservancy reserve. A 25 minute trail leads to a large secluded pond, perfect for a refreshing swim. Braeburn feels like a treehouse, with expansive windows, overlooking woods and wildlife. After a hike, grilling on the porch or dinner out, indulge in your private therapeutic year round hot tub.

Top guest favorite
A rustic cottage is viewed at sunset, with vibrant hues of orange and pink illuminating the sky. A gravel pathway leads to the entrance, framed by green lawns and decorative flower pots. Trees are visible in the background, enhancing the natural setting.
Guesthouse in Orland
5 out of 5 average rating, 125 reviews

The Greenhouse Cottage

We feel that the best way to describe our getaway to be “Rustic Elegance”. When you walk through the door you will instantly feel the warmth of a uniquely styled Adirondack cottage. Located nearby to the Acadia Highway (aka Route 1), we are close by to historic Fort Knox, Castine, and Acadia. Enjoy our attached “Greenhouse” which has been made over into a delightful screenhouse/patio, the country setting, blueberry fields, and the beautiful sunrises and sunsets! Fire pit, horseshoes, more!!!

Guest favorite
A quaint cabin is nestled among lush greenery, featuring a shingled exterior and a red door. Flowering plants adorn the nearby area, and a rustic chair is visible on the grass. Natural light creates a serene atmosphere in this peaceful rural setting.
Guesthouse in Appleton
4.89 out of 5 average rating, 314 reviews

Raven's Crossing - Retreat Cottage

Welcome to Ravens' Crossing , an 1850's farm located in Midcoast Maine in Appleton. With two guest cottages to choose from, you will find yourself in a peaceful, quiet space. Hot tub is working! Breakfast is $40, delivered to your cabin. Shared bath at studio, short walk from cabin; out-house at cabin Whether you choose to receive massage, relax in the sauna, stay in a cottage, you can decide how your retreat desires may be met. Retreat cabin is off-grid. There is a studio apartment for guests

Guest favorite
A cozy blue cottage is set among snow-covered trees, with a welcoming red trim around the door and windows. Three dogs sit in the foreground, showcasing their friendly demeanor, while a small sled leans against the cottage, suggesting winter activities nearby.
Guesthouse in Washington
4.95 out of 5 average rating, 155 reviews

Fox and Bird Retreat on Davis Stream

Our off-the-grid, solar-powered cottage is nestled within our 18 acres in the town of Washington, Maine. The cottage borders a beautiful stream, is surrounded by tall pines and is several hundred feet away from our home, providing a very private and serene experience. Guests can wander or snowshoe on our property, relax in the screen house next to the cottage or hang by the accessible fire pit. We are close to many local lakes and hiking trails and only 30 minutes from Camden & Rockland.

Top guest favorite
A comfortable living space is complemented by large windows offering expansive views of the surrounding countryside. A gas fireplace adds warmth, and a ceiling fan provides airflow. The seating includes a leather chair and a sofa adorned with decorative pillows, set over a soft area rug.
Guesthouse in Winterport
5 out of 5 average rating, 113 reviews

Winterport Evergreen Farm - Guest House

Relax & enjoy a private, peaceful stay at this beautiful Christmas tree farm in Winterport. We offer the perfect spot for nature lovers and couples! Conveniently located 20 minutes from both Bangor and Belfast and 75+/- mins from Acadia National Park. After a day of adventuring on or off the property, unwind around the fire pit or on your deck. This property has woodland trails that cover 200+ acres that includes a pristine farm pond. Couples who love cooking will relish the appointed kitchen

Top guest favorite
A serene sleeping area features a spacious bed adorned with neutral-toned bedding. Two bedside tables are positioned beside the bed, each with a lamp. A wooden bench is placed at the foot of the bed, and a seating area with a chair and small bookshelf is visible in the corner.
Guesthouse in Franklin
5 out of 5 average rating, 109 reviews

The Spot - Water Views

Nestled in a small quiet town right on the banks of Taunton Bay, enjoy peaceful relaxing location and watch the tide roll in and out. Wake up to waterviews from your bed. You have the entire "Spot" to yourself and whatever wildlife happens to show up that day! ***Shoulder Season is upon us and this is a great opportunity to experience Downeast Maine and all of Acadia with less crowds and no vehicle reservations for Cadillac Mt required after October 26th and all of November and December.***

Guest favorite
The interior of the tiny house is shown, featuring a well-equipped kitchen with a two-basin sink and a countertop extending into a cozy seating area. A wooden ladder leads to a loft, and large windows allow natural light to fill the space.
Guesthouse in Surry
4.89 out of 5 average rating, 308 reviews

Tiny Home on Newbury Neck

This efficient tiny house is located on Newbury Neck in between Morgan bay and Union river bay. Queen bed, kitchen, bathroom, washer & dryer. Has everything you need and nothing more. Perfect for a solo stay or for a couple. Close to Acadia National Park, Blue Hill, and quiet beaches. Jack is a licensed boat Captain through the U.S. Coast Guard and offers a discounted sail charter to our guests aboard our 36 ft. Catalina, Luna. Or, hop the lobster boat, Otter, to explore the local islands.

Top guest favorite
A spacious bedroom is illuminated by natural light from two skylights and a large window. A queen-sized bed is positioned with bedside tables featuring lamps on each side. A comfortable chair is placed in the corner, accompanied by a round area rug on the floor.
Guesthouse in Lincolnville
4.98 out of 5 average rating, 198 reviews

Peaceful Suite - Hiking, Beach, Nature

Welcome to the “East Wing”! The complete apartment is new: salt box style with beautiful views of nature (hummingbirds, fireflies, starry skies). The East Wing is first to greet the sun in the morning. Enjoy your coffee on the private deck, or sip wine at night by the fire pit. Close to Tanglewood Rd (4H camp) , Camden Hills State Park trails, and Lincolnville Beach(1 -2 miles). The area is quiet- yet just a few miles away from shopping and restaurants in Camden, Belfast, & Rockland.

Top guest favorite
A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.
Guesthouse in Orland
4.99 out of 5 average rating, 180 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Top guest favorite
A serene landscape captures a vibrant sunset over a tidal bay, with hues of orange, pink, and purple reflected on the water's surface. Silhouettes of distant trees line the shore, framed by rocky terrain in the foreground.
Guesthouse in Penobscot
4.98 out of 5 average rating, 243 reviews

Sea Pearl

This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

Guest favorite
A vibrant sunset paints the sky in shades of pink and purple, reflecting upon the tranquil surface of the lake. Silhouettes of trees frame the scene, while a small dock extends into the water, inviting peaceful moments by the shore.
Guesthouse in Orrington
4.9 out of 5 average rating, 124 reviews

Lake Escape

Lake Escape is located on Brewer Lake in Orrington. From this location, you have a view of the lake and access to the water directly across the street down a hill. The ambiance of loon calls, fresh air, and the sounds of water all make for glorious sleep and relaxing memories. The water is warm and clear for summer swimming! This recently renovated private apartment is 20 min. to Bangor, 50 min. to Acadia National Park, 25 min. to Bucksport (Fort Knox), and 50 min. to Castine.

Guest favorite
A small guest house is set amidst lush greenery, featuring a dark exterior with large windows. A bright green door provides a striking contrast. The surrounding trees and plants contribute to a natural, secluded atmosphere that emphasizes privacy.
Guesthouse in Sedgwick
4.96 out of 5 average rating, 301 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

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