Holiday houses in Jackson

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Jackson

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top Guest favourite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5.0 out of 5 average rating, 157 reviews

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 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Top Guest favourite
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
5.0 out of 5 average rating, 119 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 favourite
A spacious living area is illustrated, featuring a comfortable blue sofa with decorative pillows. A rustic wood stove is positioned near the center, accompanied by warm natural light streaming through multiple windows. A decorative area rug adds a touch of color to the wooden floor.
Cabin in Searsmont
5.0 out of 5 average rating, 28 reviews

Birch Cottage · Just You & Quantabacook Lake

Kick back and relax in this serene, stylish, and newly renovated space. Birch Cottage is the perfect rustic waterfront getaway--a retreat for couples and solitude seekers. Unwind and escape to this enchanting, woodsy, lakefront property on gorgeous Quantabacook Lake. Cottage is ideal for both romantic couple retreats and peaceful solo excursions. Nestled among tall pines and just feet from shore, this magical haven offers breathtaking views and a tranquil atmosphere for your holiday getaway.

Top Guest favourite
A charming cabin is surrounded by a landscaped garden, featuring a stone border and various plants, including flowers and greenery. The entrance is marked by a yellow door, and seating areas are positioned nearby, creating a tranquil atmosphere in a forested setting.
Tiny home in Monroe
4.97 out of 5 average rating, 36 reviews

The Cabin at Lawson Woods

Reconnect with nature at this unforgettable escape. The cabin is tucked into the forest in Mid Coast Maine offering a cozy retreat for a single looking to get away and unwind or an intimate couple who wants to retreat into the woods to connect. Completely independent of the main home, The cabin at Lawson Woods is a haven for the nature lover or anyone looking to get away from it all. Stay connected with wifi , chill with your favorite series, or take a walk out back to completely unwind.

Top Guest favourite
Vibrant gardens filled with blooming yellow irises and pink flowers are set against a backdrop of lush green trees. A cozy brown house is partially visible, surrounded by the rich greenery of the lawn and flower beds, inviting a serene outdoor environment.
Apartment in Unity
4.98 out of 5 average rating, 101 reviews

The Heron's Nest Cozy apartment in the woods.

If you like to fall asleep to the call of the barred owl, this is the place for you. This newly constructed apartment is nestled in a lovely, quiet 70 acre parcel, surrounded by nature, wildlife, gardens, trees and wetlands. Landlord also lives in detached house on property. 1 bedroom, 1 bath, 2nd floor fully furnished apartment. ~900 sq ft. 1 stall in garage available for use. New construction and appliances. Rinnai heating system. Wi-fi. Come see why, I say there is ‘no place like home.’

Top Guest favourite
A shaded outdoor seating area is positioned under a wooden overhang. Four green chairs and a coffee table create a relaxed atmosphere, complemented by a stack of firewood nearby. The entrance to the cabin features a white door with orange accents, inviting guests inside.
Home in Dixmont
5.0 out of 5 average rating, 35 reviews

Hillside Retreat

Relax and unwind at this peaceful place to stay. This cozy, cabin-themed 2 bedroom home sits on 55 acres of private land less than 30 minutes from the Maine coast. Enjoy viewing wildlife from the large windows while enjoying the warmth of the wood stove or exploring the half-mile mowed trail with hill views. This is a comfortable and centrally located property perfect for those that plan to enjoy both the ocean and central highlands of Maine. Hoping for a restful escape...here it is!

Top Guest favourite
A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.
Tent in Brooks
4.92 out of 5 average rating, 262 reviews

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.

Top Guest favourite
Cabin in Liberty
4.93 out of 5 average rating, 43 reviews

Modern Cabin on Crie Hill

Unwind at this secluded hillside hideaway. Perched above the valley with sweeping ridge views, this newly built cabin blends comfort with privacy. Begin your day soaking in the outdoor tub as morning mist drifts up from the valley below, or gather around the granite fire pit in the evening while grilling under the open sky. Designed with sustainability in mind, the retreat runs on solar power backed by a quiet propane generator to ensure a worry-free stay even on cloudy days.

Top Guest favourite
An outdoor dining area is featured with a sturdy table and chairs, shaded by a large umbrella. A grill is positioned nearby, with an expansive view of lush green hills and a clear blue sky stretching into the distance.
Home in Freedom
4.98 out of 5 average rating, 48 reviews

Halcyon Ridge

Halcyon Ridge is owned by Lynn & Chuck Hadyniak, who live nearby. Lynn & Chuck moved out of New Jersey years ago to get away from the hustle & bustle, & raise a family in peace. They love Freedom for its quiet & natural beauty, & would love to host people at Halcyon Ridge who also want to escape the noise. Stargazers will be delighted: low humidity, expansive view of the southeastern sky, & next to no light pollution, make for wonderful viewing. Rest. Relax. Recharge.

Top Guest favourite
A cozy bedroom features a king-sized bed with a textured blue coverlet and accent pillows. Two windows provide natural light, while decorative lamps sit atop the bed's headboard. A fan is positioned nearby, and a vibrant orange door adds a pop of color.
Home in Brooks
4.98 out of 5 average rating, 151 reviews

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

Top Guest favourite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 451 reviews

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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top Guest favourite
The main living space features a modern kitchen with light wood cabinetry and dark appliances. A dining table sits center, surrounded by chairs. Large windows provide an abundance of natural light, while a cozy seating area invites relaxation. A wood stove is present for warmth during colder months.
Cabin in Jackson
4.99 out of 5 average rating, 209 reviews

Forest Cabin w/ Stunning Wall of Windows

Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

Popular amenities for Jackson holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Waldo County
  5. Jackson