Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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

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Top guest favourite
A lakeside cottage is nestled among trees, featuring wooden siding with flower boxes beneath the windows. The property slopes down to a clear lake, with light filtering through the surrounding foliage, creating a serene natural environment.
Cottage in Lincoln
5 out of 5 average rating, 96 reviews

The Nest will be your Maine recreational retreat!!

The Nest is our lakeside cottage in the ❤️ of Maine’s recreational playground. You are steps from a crystal clear spring fed lake; we are also situated on ATV and snowmobile trails. Enjoy the calls of the loons & waves lapping at the shore; take in the incredible sunsets over the lake & unwind in front of the fire. We welcome your well behaved pups, please review our house rules for pet details. This is the perfect spot to recharge your batteries. We look forward to seeing you at The Nest!

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.

Top guest favourite
A cozy camp is surrounded by tall trees, showcasing a classic A-frame roof and a porch with seating. The white exterior is complemented by green trim, while areas of orange pine needles cover the ground. The setting reflects a serene, natural atmosphere.
Cottage in Brownville
4.98 out of 5 average rating, 121 reviews

Perfect Lakeside Getaway!

The perfect lakeside getaway spot with beautiful views. It is renovated with an old time cozy camp feel, with modern conveniences. This pet friendly camp is across the street from Schoodic Lake. The cozy camp sleeps 5-6 comfortably with on-site parking for three. The camp is located on ITS 111 trails for snowmobiling and ATVing. Hunting, fishing and hiking destinations include, Baxter State Park, Gulf Hagas, and Katadin Iron Works. Water access at Knights Landing just a short distance away.

Top guest favourite
A hand holds a cup labeled 'Maine' against a backdrop of shimmering water reflecting vibrant autumn foliage. The still water is bordered by large rocks and trees, enhancing the serene atmosphere.
Cabin in Burlington
4.95 out of 5 average rating, 206 reviews

Secluded Waterfront Cabin

Please Message me to ask about possible discounts and length of stay minimums. Secluded four season cabin is located on remote Saponac Lake in Burlington, Maine. Last camp on a private dead end road with clear views of the lake. Perfect location for fishing, kayaking, or just relaxing in a hammock. Fully furnished with A Minisplit Heat Pump/ AC, and Propane "wood stove" well water, and high speed WiFi. Within 30 minutes of Lincoln and 1 hr of Bangor. Both towns have shopping, restaurants,etc.

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

Guest favourite
A welcoming entryway features a rustic door adorned with a wreath. To the side, a cozy wicker chair with a patterned cushion invites visitors. A small window above a decorative shelf allows natural light entry, enhancing the overall charm of the entrance.
Home in East Millinocket
4.92 out of 5 average rating, 24 reviews

Beautiful, remodeled 3 bedroom home

Lots of room for the whole family in this beautifully remodeled 3 bedroom 1 &1/2 bath home with laundry room. Conveniently located in town close to atv and snowmobile trails. Also close to local grocery store restaurants ect. Within miles of Baxter State Park, Appalachian Trail and much much more. Whether your coming to hike, snowmobile, enjoy the fall foliage or just on business you will enjoy this comfortable home. (While this home is private it does have an attached 1 bedroom apartment.)

Top guest favourite
The interior of the custom-built yurt features a high, circular ceiling with a skylight at its center. A modern kitchen with stainless steel appliances is visible, alongside a spacious countertop. A loft area is accessed by a wooden staircase, with wooden beams and walls enhancing the natural aesthetic.
Yurt in Medway
4.95 out of 5 average rating, 171 reviews

Katahdin Riverfront Yurt

Glamping at its best! Beautiful custom built yurt on the banks of the Penobscot river along the Grindstone Scenic Byway. Close to Baxter State Park and majestic Mount Katahdin as well as Katahdin Woods and Waters National Park. Two miles to Penobscot River Trails with miles of groomed cross country skiing and mountain biking. 4 seasons of hiking, biking, fishing, canoeing, kayaking, white water rafting, skiing, and miles and miles of snowmobiling! 1 hour to Bangor 2 hours to Bar Harbor

Top guest favourite
A charming cabin features a wooden deck with seating, surrounded by lush greenery. Tall trees and a serene atmosphere are present. The exterior showcases log construction and several large windows, allowing natural light to enter the interior.
Cabin in Lincoln
4.93 out of 5 average rating, 30 reviews

Peaceful Cabin on Center Pond

Relax any time of year at our peaceful cabin in the Maine woods. Situated on the shore of Center pond, the cabin has been appointed with all the amenities you would hope to find. 2 bedrooms each with a Queen sized bed (1 up-1 down) a loft with 2 twin beds, and 1 & 1/2 baths, the cabin comfortably sleeps 6. Upstairs is accessed by a spiral staircase. The fully furnished kitchen has everything you need to cook a full meal. Relax and sunbathe, swim, paddleboard or kayak the Summer days away.

Top guest favourite
A spacious living area features comfortable seating arrangements with a leather sofa and wooden chairs. Large glass doors provide access to a view of the lake, while a wooden dining table is positioned near the window. Natural light fills the room, highlighting the wood flooring.
Cottage in Lincoln
4.97 out of 5 average rating, 31 reviews

Panoramic view lake cottage

Cottage with 175 feet of waterfront. Enjoy panoramic views of a crystal clear spring-fed lake. Cottage has 1 bedroom/1 bath plus full size futon in living room. Smart TVs in living room and bedroom. Washer & dryer in bathroom. Heat pump/AC. Linens, cable, WiFi, grill, firepit provided. During summer, floating dock, 4 kayaks, canoe & swim platform. At end of quiet dirt road. 4x4 or AWD recommended during winter months but road and driveway are snow plowed. Come rest, relax and recreate.

Guest favourite
A fire pit surrounded by stone offers warmth and light against a darkening sky. A spacious, newly renovated farmhouse with large windows is visible in the background, accentuated by the soft glow of outdoor lighting. Chairs are arranged nearby for seating.
Home in Lincoln
4.89 out of 5 average rating, 27 reviews

Lincoln Park Lakeside

LARGE yard and centrally-located! Your family will be close to everything when you stay at this lake view home. Bring your boat/trailer or water toys for all recreational water sports, fishing and swimming! Boat ramp just steps from house, along with public beach and dock, playground, ping pong table, and basketball court. Walk downtown just a block away to Restaurants and stores. Stroll over to Steaks N Stuff to grab some premium meat to throw on the bbq or just hang out in the yard

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, 63 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.

Superhost
Cabin in Glenburn
4.78 out of 5 average rating, 117 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 Chester holiday rentals

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