
Holiday houses in Jackson
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Top-rated holiday rentals in Jackson
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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!

Cute Midcoast Cottage w Hot Tub
Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Cozy Cottage on the Penobscot — Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Wall of Windows - Super Clean & Solar-powered
This newly constructed 850 sq ft cabin features a wall of windows and is located on a 30 acre forest. It is perfect for those seeking a peaceful and cozy space to relax and breathe deeper while experiencing the brilliance of Mid-Coast Maine. Wake up to the gentle morning sun cresting over the trees, linger at night under the magic and mystery of a star-filled sky, and witness what all four seasons have to offer. Belfast and Unity are close w/ Bangor, Camden, Rockland, & Acadia - easy day trips.

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.

Quiet cottage on the bay
Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Belfast Harbor Loft
Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Cozy Belfast Home Away from Home
This house is walking distance from downtown Belfast, Belfast Rail Trail, and Belfast Harbor. It's a romantic nest for two or a crash pad for up to six. Live comfortably while gaining easy access to all the cool adventures Mid-Coast Maine offers. Please note this is an older house with a basement sump pump. It is eco-friendly - I don't use pesticides. You may see harmless house spiders. It is NOT a good fit for those with severe dust or mold allergies, or with severe cat allergies.

Little Apple Cabin on 5 acres, amazing stargazing!
Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.
Popular amenities for Jackson holiday rentals
Other great holiday rentals in Jackson

The Colby House - Built in 2025!

Carriage House at Bald Hill Cove

Owls Nest at Eight Acres

The Cabin at Lawson Woods

The Swan Lake House - Lakefront-Private Beach

Top of the World

Loon Cove Cottage

Wildwood Acadia Salt House: 55 minutes from Acadia
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- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Belgrade Lakes Golf Club
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Sand Beach
- Bear Island Beach
- Lighthouse Beach
- The Camden Snow Bowl
- Eaton Mountain Ski Resort
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Farnsworth Art Museum
- Rockland Breakwater Light
- Narrow Place Beach
- Islesboro Town Beach
- North Point Beach
- Three Island Beach
- Driftwood Beach
- Pebble Beach
- Billys Shore




