Holiday rentals in Charleston

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Top-rated holiday rentals in Charleston

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

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Top guest favourite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.94 out of 5 average rating, 235 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Top guest favourite
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.
Guest house in Corinna
4.96 out of 5 average rating, 26 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 favourite
The A-frame chalet features a green metal roof and a wooden exterior, set amidst lush greenery. A small balcony with flower pots is visible on the upper level, while a vintage vehicle is parked nearby on the grass.
Tiny home in Atkinson
4.95 out of 5 average rating, 158 reviews

Cozy Rural A-Frame in the Middle of Maine.

Get away from it all when you stay under the stars. This chalet is right on the ITS trail, nestled in the middle of a small lightly wooded lot in a rural setting. Enjoy the fire pit, bring your snowmobiles, bikes and trailers. The space is cozy with a 55" TV and small kitchen to prepare your meals. The bedroom is in the loft with catwalk opening up to a balcony. Enjoy access to year round outdoor activities as you are nearby Katahdin Iron Works/Jo Mary region and near Sebec and Schoodic lakes

Superhost
Cabin in Glenburn
4.79 out of 5 average rating, 118 reviews

Acadia Pines Retreat HotTub-10 Min Downtown Bangor

Hot tub. Nature. Total peace. 🌲Acadia Pines Retreat-just 10 minutes from downtown Bangor and close to Acadia National Park. Warm wood ceilings, curated interiors, and cozy moments in the beautiful Maine woods. This retreat features open-concept living space styled with rich textures, soft lighting, and designer touches throughout. Sink into plush seating, enjoy slow mornings with coffee at the stone island, or unwind after exploring surrounded by stillness of forest in your private hot tub.

Top guest favourite
A stylish bedroom features a spacious bed with intricate bedding, complemented by a decorative tapestry and an oil painting on the wall. Soft lighting from bedside lamps adds warmth, while a ceiling fan provides airflow in the inviting atmosphere.
Flat in Old Town
4.95 out of 5 average rating, 118 reviews

The Sovereign Suite - Cozy/Convenient/Home Theater

Relax in this rural yet convenient apartment with easy access to Old Town and just a couple miles from I-95. Find comfort in a stylish bedroom or enjoy a premium home theater experience with a 77inch 4k HDR TV and surround sound. Well stocked kitchen and complimentary coffee and tea is included. New steam washer/dryer are available for your use as well as high-speed Wi-Fi. An office space is available for those that work from home. Quiet area with much wildlife to enjoy around the house!

Top guest favourite
A bright, open space features large windows that allow natural light to fill the area. A wooden desk with two chairs is positioned near the windows, complemented by a small plant. The warm wood beams and floors enhance the inviting atmosphere.
Barn in Corinth
4.99 out of 5 average rating, 69 reviews

The Barn at Forest Hill.

We are about 30 minutes to downtown Bangor and about 1:30 minutes to Acadia, we have had our fair share of guests visiting Acadia. We are in a secluded location sitting on 60+ acres and run on solar power. The barn is an attached structure to our main dwelling. The barn has wood heat, propane wall heaters as backup, and sleeps six people comfortably. Big sky, views with hills and fields. We also welcome snowmobiles, with snowmobiles trails (ITS 83 and 84) passing through our property.

Top guest favourite
A rustic lodge is set amidst vibrant fall foliage, featuring a green metal roof and a welcoming porch. Large rocks and gravel surround the structure, providing a natural feel. Sunsets reflect against the lake visible in the background, enhancing the tranquil atmosphere.
Cabin in Orneville
5 out of 5 average rating, 64 reviews

Lake View Lodge; Rustic Retreat on Boyd Lake Maine

Be a part of history and make it at the same time by staying at this recently renovated home with stunning views of Boyd Lake, Maine. It's perfect for a family/friends retreat or a romantic getaway. Read a book. Explore the lake with your kayaks. Take a day trip to Bar Harbor or Acadia. Come home and relax by the campfire. Listen to the loons while you stargaze from your private dock. Boats, jet skis & ATVs welcome. Start making memories at Lakeview Lodge that will last a lifetime.

Top guest favourite
A wood stove stands prominently in the living area, featuring a brick facade and a stainless chimney. The warm glow of the flames is visible inside the stove, providing a cozy element to the space. The surrounding area has hardwood flooring and wooden walls.
Cabin in Williamsburg
5 out of 5 average rating, 32 reviews

Private Log Home Escape near Trails, Lakes, ATVing

Discover Your Perfect Getaway at Our Charming Ward Cedar Log Home Nestled in Williamsburg Township, our log home offers a peaceful escape from everyday chaos. Enjoy the tranquility of the Maine Wilderness while being just a short drive from town and local amenities. Whether you're into hiking, hunting, fishing, ATVing, snowmobiling, leaf-peeping, or just relaxing by the lakes, this is the place for you. Your private retreat awaits, ready for unforgettable adventures and relaxation.

Top guest favourite
A lakeside cabin is framed by lush green trees, showcasing a wooden dock that extends over calm waters. The structure features large windows and a deck with outdoor seating, providing a serene view of the lake and surrounding nature.
Cabin in Hudson
4.9 out of 5 average rating, 123 reviews

Waterfront| Fire pit| Deck|Kayaks

Come and make lifelong memories at The Eagles Nest on Beautiful Pushaw Lake! Newly renovated loft provides a unique camping like experience for children...or allows Adults to revisit their inner child. -Explore the lake with the one tandem and 2 child kayaks provided -Enjoy Barbecuing with our 4 burner grill on the outside deck just feet from the waters edge -Take a swim or relax with a good novel on the outside Hammock -Many family friendly nearby trails to hike and snowshoe

Guest favourite
A charming green cabin is nestled among trees, featuring a sloped roof and a small porch. Nearby, a propane tank and air conditioning unit are visible. Lush greenery and a simple gravel path surround the structure, creating a serene outdoor atmosphere.
Cabin in Atkinson
4.94 out of 5 average rating, 108 reviews

Upta Camp

Take it easy at this unique and tranquil getaway. Take a hike down one of the trails out back, or swim in the cool clear water of the spring fed pond off the back porch. Cozy up during a storm by the fire with a good book, or wet a line on a clear morning off the back steps and catch supper! It’s all in one comfy cabin property to get away from it all. Only a few miles to Dover-Foxcroft, or Sebec Lake. Far enough away to get away, but close enough to the amenities and sights.

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, 43 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 rustic dining area features a large wooden table surrounded by black chairs. Pendant lights hang from the exposed beam ceiling, illuminating the space. In the background, a fully equipped kitchen is visible, complemented by windows that offer views of the surrounding nature.
Barn in Dover-Foxcroft
4.94 out of 5 average rating, 107 reviews

1890 River Barn

Perched above the Piscataquis River, this historic barn was beautifully renovated into a rustic luxury retreat. Two full stories plus a loft, with relaxing river views on all levels. Gourmet kitchen/dining area with a fireplace & a cozy yet spacious lounge upstairs. Enjoy the garden and patio overlooking the river or unwind in the luxurious copper soaking tub in the loft. Designed for a couple & perfect for romantic getaways, yet comfortable to sleep up to 4 guests.

Popular amenities for Charleston holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Penobscot County
  5. Charleston