Family-friendly holiday rentals in Winterport

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

Hidden Gem

This recently renovated home is located in the heart of historic Winterport, Maine. It’s located on a quiet street with views of the Penobscot River. Winterport is an old fashion, quaint town, where everyone is very friendly. The home has three bedrooms and one bath with plenty of room to spread out. This house is so centrally located its only 52 miles to Bar Harbor and Acadia National Park, 21 miles to Belfast and 40 miles to Camden just to name a few of the beautiful coastal towns in Maine.

Tiny House oasis in Beautiful Waldo County. We❤️🐕

We have an adorable rustic & comfy tiny house; warm & cozy, with a big queen bed & AC. LAST MINUTE DISCOUNT September 7th through 11th. Check it out! There is a fridge, tea kettle, toaster oven & stovetop. Try our new outdoor shower building. There's a composting toilet indoors which works well & smells not at all. NO INDOOR PLUMBING but we supply drinking/cooking/washing water & there is a sink that drains. If you have more people & your own camping equipment, look for our other listing.

Tiny House at Wooded Bliss Homestead

On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

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!

The Little House at Lone Spruce

Wake up surrounded by UMaine certified pollinator gardens and goats right outside your window in this sweet, cozy tiny house on our beautiful working farm!This has an outhouse, hot/cold water dispenser, foot pedal sink. NO SHOWER or running water. This is a rustic, comfortable stay. Farm provisions from our fully licensed kitchen/creamery can be purchased as available within seasonal availability 45 min to Acadia, 20 min to Bangor, 25 min to Ellsworth. 7 min to hiking/biking trails

The Downtown Loft Bangor

Not just another AirBnB "hotel"! A historic building, the Loft has been fully renovated with a modern, minimalist vibe. Your private escape in the heart of downtown Bangor. Comfy king bed, luxury bath, chef's kitchen, top -rated king sofa bed, and massive windows that open to an expansive view of Main Street! 0.0 miles to all things Downtown Bangor 0.5 miles to Waterfront Concerts 0.9 miles to Hollywood Slots 1.0 miles to Cross Insurance Center 1.2 miles to Eastern Maine Medical

Waterfront Tipi Glamping // Phoenix Landing

Majestic private waterfront Tipi * on a lake. Quiet nature oasis with hot tub, woodstove, firepit, modern grill, and all the essentials. Ice skate or xc-ski across the frozen lake and watch the bald eagles fly overhead, or relax in the Adirondack chairs in front of the bonfire while you make smores and cook dinner on the grill or over the open fire, then snuggle up inside the tipi while you listen to vintage vinyl and let the owls hoot you to sleep. *Tipi closed March-April.

Penobscot River Views - Two Room Suite!

Two room suite on the first floor of my home with an en-suite private bathroom and views of the Penobscot River/Bay! ***Just under an hour drive to Acadia.*** Convenient access right on Route 1. A short walk to the Sandy Point beach park. Comfortable queen bed and sleep sofa. Two 40” HD TVs with Roku. Mini fridge, microwave, toaster oven and induction burner in room. Almost 400 SF of space! If you need more beds, please see my listing for the room upstairs.