Guesthouse vacation rentals in Penobscot County

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Top-rated guesthouse rentals in Penobscot County

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Top guest favorite
The cottage door welcomes visitors with a polished wooden sign that reads 'THE COTTAGE.' Sunlight filters through the glass panel, revealing glimpses of the kitchen interior, where natural light brightens the space and highlights green plants on the windowsill.
Guesthouse in Corinna
5 out of 5 average rating, 17 reviews

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

Guest favorite
A two-story guest house is surrounded by lush greenery, featuring a simple exterior with horizontal siding. Large windows allow for natural light, while two garage doors are visible at ground level. The gravel area in front offers space for parking.
Guesthouse in Piscataquis County
4.86 out of 5 average rating, 36 reviews

Desirable guest house in Brownville ME. Sleeps 8.

Memories to be made at our desirable 3 bedroom four season guest house. Just a minute walk to Schoodic Lake, where the swimming and fishing are spectacular. Enjoy the sunrise from the lakeside windows or catch a glimpse of Mount Katahdin from the dock. Access snowmobile and Atv trails from the property. Fully equipped kitchen. Washer and dryer. Includes linens. Large parking area. Outside bbq grill and fire pit. Games and books to use. Short drive to Gulf Hagas and Baxter State Park. Great WiFi

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 private deck features two white Adirondack chairs positioned on a patterned outdoor rug. A potted plant adds greenery, while a sail-like shade offers protection from sunlight. Large windows provide an inviting view of the surrounding trees and nature.
Guesthouse in Winterport
5 out of 5 average rating, 20 reviews

Carriage House at Bald Hill Cove

Maine, the way life should be! A perfect relaxing getaway and rejuvenating escape from the hustle and bustle. Welcome to our tranquil retreat nestled against the backdrop of Bald Hill Cove. Carriage House offers serene river views, a wooded fire-pond, and occasional wildlife in the nearby apple orchard. Days begin with the symphony of birdsong and end with star filled night skies. Private entry, parking, and waterfront facing deck included. Come experience the magic of rural living!

Top guest favorite
A charming cabin is set against a backdrop of a clear blue sky, surrounded by a vast expanse of snow-covered land. Trees line the horizon, framing the peaceful winter scene. A frozen pond can be seen in the foreground, reflecting the winter landscape.
Guesthouse in Patten
5 out of 5 average rating, 27 reviews

Black Bear Pond Cabins

Wake up to the most beautiful sunrises! This wonderful North Woods cabin envelopes you in pine paneling and has a porch overlooking a trout pond and almost 500 acres of a private estate on the highest hilltop around. Play where the animals do - moose, bear, beaver, and eagles all call this home. Hike fields and woods or visit our private 10-acre pond. Catch a glimpse of our resident white crow. Watch the sunset over Katahdin. Close to Baxter State Park, Katahdin Woods and Waterways Nat'l Park

A serene sunset over Schoodic Lake is captured through the silhouettes of trees. The sky displays warm hues of orange and pink, reflecting on the calm water surface, creating a peaceful scene. The horizon fades into a darker shade, enhancing the tranquility of the lake.
Guesthouse in Brownville
4.82 out of 5 average rating, 145 reviews

A Little Piece of Heaven

Our place is good for couples, solo adventurers, business travelers, and families (with kids). 3 night minimum. Cottage is located at 32 Lake Avenue, Brownville, Maine 04414. Turn right at A.E. Roberson's convenience store in Brownville, Maine onto Church Street. Follow Church Street for 4.7 miles and turn right onto Schoodic Lake Road. Follow Schoodic Lake Road for Approx. 4 miles. Bear right after crossing the railroad tracks and 32 Lake Ave. will be on your left at our mail box.

Top guest favorite
A single-story house featuring a warm, natural exterior with wooden siding and a red accent. A welcoming porch, with red chairs, overlooks a landscaped area with large stones. The surrounding vegetation includes tall trees, contributing to a serene outdoor environment.
Guesthouse in Newport
4.97 out of 5 average rating, 99 reviews

Cozy Bungalow

Only 25 minutes to Bangor medical facilities We added a cozy addition to our garage for guests to share our water front property. Your own private dock and small beach area Plenty of parking for your Utv or snowmobiles The Rail Trail is at the end of our driveway WiFi BBQ grill Washer and dryer Full-size fridge with freezer Picnic table Kayaks There is no stove to cook on inside, I am trying to avoid food smells inside. There is a new gas grill with side burner for outside cooking

Guest favorite
A warm living area is featured with wooden ceilings and a neutral carpet. Two comfortable sofas are positioned around a cozy space. A laundry unit is visible, with a kitchen area in the background. Large windows offer views of the outdoors.
Guesthouse in Enfield
5 out of 5 average rating, 33 reviews

2 Bedroom Apartment on Cold Stream Pond

2 bedroom, 1 bath apartment over garage. Full kitchen. Access to Cold Stream Pond for both summer and winter recreation. Kayaks and some other items able to be enjoyed by guests. Sit back and listen to the distant waves of the water, the loons & wildlife, and the rustling leaves. Spend time in the summer along the shore front and on the lake, watch the breathtaking colors of fall, or experience winter wonderland on one of Maine’s most popular lakes for summer and winter recreation.

Superhost
Guesthouse in Sangerville
New place to stay

Stylish Guest Loft – Cozy & Quiet Stay

Kick back and relax in this calm, stylish space. Welcome to your private retreat above the garage — a brand-new, open-concept studio finished with tongue-and-groove pine. Perfect for one or two guests, it features a cozy queen bed, futon, and a bathroom with a stand-up shower. Accessed by stairs, this peaceful hideaway in Sangerville is ideal for couples or solo travelers seeking a quiet escape. We look forward to hosting you! Plenty of parking. Room for a trailer. Big yard.

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.

Top guest favorite
Guesthouse in Brownville
5 out of 5 average rating, 9 reviews

Hike Katahdin Bunkhouse.

A great place to stay with lots to do within 20 miles. We’re actually in Ebeemee twp. The bunkhouse is super cozy and private. There is hiking, swimming, kayaking, canoeing nearby. We also have great snowmobile trails which can be accessed from our back yard. We are near Baxter state park, Mt. Katahdin, Gulf Hagas, Pleasant River and JoMary lake. Acadia national park is a day drive, and well worth it. I would suggest a three night stay if you want to visit Acadia.

Guest favorite
The loft area features warm wooden walls with two mounted moose heads, highlighting rustic charm. A wooden railing surrounds the loft, providing a view of the living area below. Natural light is softly illuminated by recessed lighting along the ceiling.
Guesthouse in Sangerville
4.94 out of 5 average rating, 53 reviews

Richardson's Rental Dover-Foxcroft Maine

Brand new construction. This unit is located behind the main house. The cabin has one bedroom, one full bath, open kitchen/living area/dining, half loft and radiant heat. Direct access to snowmobile/atv trail system. 50 minutes from Bangor, 50 minutes from Greenville. 90ish minutes from Bar Harbor/Acadia National Park. Sebec Lake is just minutes away. This is a unique get a way for those that want to explore or sit by the campfire and relax. Directly on ITS 85.

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