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, 236 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.

Top guest favourite
A tiny home features a covered porch with wooden screens, surrounded by green grass and trees. A red firepit structure sits on a stone base nearby, enhancing the outdoor space. A gravel driveway leads up to the home, suggesting ample parking.
Tiny home in Howland
5 out of 5 average rating, 62 reviews

The Howland Hideout

Welcome to The Howland Hideout | Cozy Private Maine Retreat for Couples, Solos & Small Families. Filled with the necessary amenities for a comfortable stay and boasting handcrafted touches throughout, you won’t find many places quite like this! Could be a great fit for traveling nurses as there are multiple hospitals nearby. This family friendly location has a large parking area with plenty of room for vehicles/trailers and the patio/backyard are a great place to relax and enjoy the outdoors.

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

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, 70 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 bright living space features a comfortable seating area with a tan leather sofa and two armchairs. Large windows provide natural light and a view of the greenery outside. A dining table with chairs and a kitchen area are visible, enhancing the open layout.
Home in Old Town
4.99 out of 5 average rating, 68 reviews

River Apt by UMaine

Enjoy easy access to all the best Maine has to offer from this perfectly located home base on the Stillwater river. Walk to the UMaine campus, just .5 miles away. Walk, bike, or cross-country ski miles of beautiful trails right outside your door. Have coffee on the dock or get out on the water in one of our many paddle crafts. Enjoy restaurants, bars and cafés in Orono or Old Town. We are very close to 95, making it easy to day trip to Acadia National Park, Camden, or Baxter State Park.

Top guest favourite
A serene lakeside view captures a charming house framed by vibrant autumn foliage. The scene includes a private dock extending into the calm water, surrounded by trees in hues of orange, red, and yellow, under a colorful sky at sunset.
Home in Orenville
4.98 out of 5 average rating, 59 reviews

Absolutely Shore; Boyd Lake Bliss, Maine

Come appreciate the beauty of Boyd Lake, Maine. Whether it is boating, swimming off the dock, relaxing with a good book, swimming, kayaking, or reconnecting with friends and family, this house will make any vacation memorable. Take day trips to some of Maine’s most treasured gems, like Bar Harbor and Acadia National Park. At night, cozy up by the gas fireplace inside or start a campfire outside while you listen to the Loons sing. Come and make “S’more” memories here at Absolutely Shore!

Guest favourite
A cozy living area features two brown leather sofas with decorative pillows, positioned around a central coffee table. Natural light filters in through the windows, and potted plants add a touch of greenery. A neutral rug anchors the seating arrangement.
Flat in Bangor
4.91 out of 5 average rating, 22 reviews

Cozy 1BR Apt Near City Center

Charming 1BR Unit Bangor Oasis! Enjoy comfort and convenience in our cozy one-bedroom apartment, perfectly located near hospitals, Bangor Airport, shopping centers, and restaurants. Features include a fully equipped kitchen, in-unit washer/dryer, off-street private parking, and streaming services on a smart TV. Nestled in a quiet neighborhood, it’s your ideal retreat. Explore cultural spots, parks, and trails all within easy reach. Book your stay and experience the best of Bangor!

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, 124 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
A charming two-story home features a light exterior with black shutters. A well-maintained lawn slopes gently in the foreground. Two small steps lead to the front door, flanked by decorative items. Large windows offer ample natural light, while nearby greenery enhances the overall appeal.
Home in Dexter
4.88 out of 5 average rating, 50 reviews

The Belle Air

Bring the whole family to this great place with lots of room for fun. Views of Wassookeag Lake. Walking distance to the public beach and boat landing. Close to ITS 85 trails for ATV's. Walking distance to downtown and Main street shops. Enjoy a sunset on the back porch and a sunrise from the enclosed front porch. Local public golf course less than one mile away. Come relax close to parks restaurants and the great outdoors! 20 minutes from Newport and 1 hour from Greenville.

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

Acadia Pines Cabin w/HotTub 10min2Downtown

Welcome to Acadia Pines Retreat, where the whispering pines and peaceful forest trails set the tone for your perfect Maine escape. Nestled just a short drive from Acadia National Park and the coast, this charming retreat offers the serenity of the woods with the comforts of home. * Peaceful, secluded location *Private hot spa jacuzzi to soak in after a day of hiking *Outdoor seating and stargazing spots 📍 Centrally located for day trips, lobster shacks, and scenic drives

Popular amenities for Charleston holiday rentals

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