Holiday houses 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, 98 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!

Guest favourite
Children are seen playing along the shoreline of a calm lake, surrounded by lush greenery and a clear sky with scattered clouds. Some children are wading in the water, while others gather near the rocks. The natural setting features various trees reflecting the serene atmosphere.
Home in Lincoln
4.84 out of 5 average rating, 25 reviews

Lakefront Life, Family Friendly

Lakefront Home/Cabin that has an authentic Maine feel. Located on the end of a maintained private dirt road, sitting about 50 ft from the water and nestled in a fairly private cove, this gem is just waiting for you. Enjoy great swimming, fishing, or just lounging on this quiet stocked spring fed lake. all the amenities you need, including washer/dryer. Plenty of parking and a public boat launch close by. Nice swimming area in front of the cabin. 2 BR, one has 2 double beds and the other 1 king.

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, 65 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

Superhost
Cabin in Glenburn
4.8 out of 5 average rating, 122 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.

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.)

Guest favourite
A functional kitchen area features wooden cabinetry and a white stove and refrigerator. A round wooden table with a single chair is positioned nearby, contributing to a cozy atmosphere. Small kitchen appliances are neatly arranged on the countertop, with a sink visible under the cabinets.
Apartment in Medway
4.95 out of 5 average rating, 86 reviews

Elkins Rental

A peaceful place for the family. If you're looking for a quiet out of the way place to stay but still close to all the recreation this area has to offer, this is the place. Baxter state park and Katahdin Woods and waters National Monument close by. ATV trails, Snowsled trails and the Penobscot river all within a couple of miles away . Excellent area for hunting, fishing, hiking, boating and all other 4 season outdoor activities. Plenty of parking area for snowmobile, atv and boats trailers.

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
4.94 out of 5 average rating, 32 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, 28 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

Guest favourite
A private dock extends over calm waters, leading to a serene lake surrounded by lush green trees. The clear blue sky reflects off the water, creating a tranquil setting ideal for relaxation and outdoor activities.
Cabin in Lincoln
4.9 out of 5 average rating, 79 reviews

Private dock, king beds, screened in porch, AC.

Cozy lake front cabin with two king bedrooms + twin bunk room. Heat pump for warmth and/or cooling. Screened in porch overlooking the lake with table for dining or playing games on a rainy day, a lakeside fire pit, private dock, and large deck with grill. Come swim, fish, kayak/canoe, relax, and listen to the loons call! 10min from I-95 and town, restaurants, and grocery store. **Dock is in the water seasonally generally June- mid September.

Guest favourite
A serene lakeside view features a grassy area leading to Cambolasse Pond. A stack of firewood stands neatly beside the water's edge, while a small boat is visible on the calm lake. Lush trees and a clear blue sky complete the peaceful setting.
Cottage in Lincoln
4.78 out of 5 average rating, 80 reviews

Home with Sandy Beach On Cambolasse Pond

Welcome to Lincoln! This Camp is Located on a beautiful 1.3 acre flat lot with ample parking, sandy beach, shallow lake access and the ability to launch your own boat right from shore! Excellent snowmobiling,swimming, boating and fishing. Located on Cambolasse Pond there is not many like this. Private pond, Very peaceful Comes with sheets, pillows, and some towels. I recommend bringing extra towels and any other essentials you may need.

Popular amenities for Chester holiday rentals

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