Guesthouse holiday rentals in Penobscot River

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 800 Mbs fiber 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. We’re very pet friendly!

Location · Family · Biking

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!!!

Family · Value · Comfort

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.

Family · Location · Cleanliness

Private oceanfront cottage- Steps to Penobscot Bay

Coastal, light and airy- this recently renovated cottage/ guest house is perfect for those seeking to explore all that Midcoast Maine has to offer. Each room offers panoramic views of spectacular Penobscot Bay. Watch for sailboats, eagles, seals and other wildlife from the deck, the Adirondack chairs, or from inside the home. Property is uniquely situated at the head of Penobscot Bay and offers stunning views of sunrise and sunset. Great amenities & comfort for guests. Perfect for couples.

Location · Family · Parks

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.

Location · Value · Barbecue

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.

Value · Location · Bathroom

BRAEBURN at The Appleton Retreat

The Appleton Retreat is a short scenic drive to Belfast, Camden, Rockport 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 1/2 hour walk on a wooded trail leads to a large secluded pond. Braeburn feels like a treehouse, with expansive windows, overlooking woods and wildlife. Enjoy grilling on the screened in porch and indulge in your private therapeutic year round hot tub.

Family · Location · Parks

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

Location · Family · Wi-Fi

Chic Farmhouse Cottage, WiFi, Private Beach, A/C

Scrupulously appointed with authentic mid-century classics mixed with farmhouse accents. Total privacy guaranteed, NO hidden cameras, 600 sqft cottage with private, furnished, covered deck and a private fenced-in & furnished garden with a natural stone fire-pit, & ROW to private beach. High speed internet, 500Mbps, cold A/C, small kitchen equipped for basic, minimal cooking. Relax on the Adirondack chairs, grill by the fire pit or dine al fresco in the garden. Parking for 2 cars.

Location · Family · Outdoor spaces

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.

Location · Family · Comfort

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.

Family · Location · Hiking

Sun-filled Hidden Carriage House

Cozy one bedroom carriage house in Bar Harbor, Maine. Located about 10 min by car from downtown, accessible to Island Explorer route. This recently updated upstairs apartment is perfect for your Acadia National Park getaway with off-street parking and a full kitchen for cooking. Kitchen includes full-size refrigerator, microwave, stove and oven. Full bath with on-demand hot water (never have a cold shower!). The bedroom has a dresser, queen bed and closet all for your use.

Location · Value · Quiet