Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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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, 202 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.

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 out of 5 average rating, 140 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 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, 116 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 cabin interior showcases a welcoming open layout with wooden walls and a cozy atmosphere. Comfortable seating is provided by leather sofas and a recliner. A wooden coffee table sits in the center, and the kitchen area, visible in the background, features wood cabinets and modern appliances.
Cabin in Enfield
4.97 out of 5 average rating, 116 reviews

28 Holiday Lane Beach Front Cabin

4-Season Cabin next to Morgan's Beach on beautiful Cold Stream Pond rented year round. This is the perfect location for a family vacation or business/working people who travel and have temporary assignments lasting one week to several months. Cabins are fully furnished and include: heat, hot water, electricity, Direct TV, WiFi, trash removal, driveway and roadway plowing. Cabins are 10 minutes to Penobscot Valley Hospital in Lincoln and 40 minutes to EMMC in Bangor. Weekly & Monthly Rates.

Guest favourite
A modern kitchen features rustic wooden accents and stone backsplash. Stainless steel appliances are arranged beside contemporary cabinetry. Two pendant lights illuminate the bar area, which has a slate countertop and three metal stools. Natural light enters through a window above the sink.
Flat in Millinocket
4.95 out of 5 average rating, 115 reviews

ABOL PLACE, home base to the Katahdin Region!

Centrally located in downtown Millinocket, ABOL Place is a relaxing and beautifully appointed home base for all of your Katahdin adventures! Whether it be hiking Baxter State Park, The Appalachian Trail, Gulf Hagas, Fly Fishing the West Branch, White Water Rafting, visiting the Woods and Waters National Monument, Mountain Biking, Boating or Cross Country Skiing at our world class cross country ski trails, ABOL PLACE is the perfect spot for friends to relax and recap the adventures of the day!

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, 162 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, 29 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 fire pit surrounded by four chairs is positioned by the tranquil waters of Molasses Pond. The scene is framed by a grove of trees, with a dramatic sky stretching overhead, reflecting the calmness of the lake.
Home in Eastbrook
4.99 out of 5 average rating, 153 reviews

The Maine Getaway - Lakefront with Beach

If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

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
4.88 out of 5 average rating, 25 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
Tiny home in Bangor
4.86 out of 5 average rating, 159 reviews

Field of Dreams Tiny Home

Cozy Tiny Home with Stunning Views Escape the hustle and bustle in this charming tiny home with serene field views. Enjoy the tranquility of nature while still being conveniently located just minutes from Bangor's airport and town center. Relax and unwind in the private Jacuzzi with stunning views of the endless field or gather around the fire pit for a cozy evening under the stars. The projector screen offers endless entertainment options, perfect for movie nights or gaming.

Guest favourite
Cabin in Lincoln
4.9 out of 5 average rating, 77 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.

Top guest favourite
Cottage in Millinocket
4.95 out of 5 average rating, 208 reviews

Stowaway Cottage Lakefront Fire Pit Sunset Escape

Stowaway is a lakefront cottage on Ambajejus Lake, just minutes from Baxter State Park, Mount Katahdin, the Katahdin Woods & Waters Monument, and Millinocket. Sleeping up to 10 in 2 bedrooms and 2 lofts, it blends home comforts with classic Maine 'camp' charm. Amenities include a swimming area, paddle boat, four kayaks, fire pit, picnic area, gas grill, full kitchen, Wi-Fi, cable TV, and AC—a perfect location for families or small reunions.

Popular amenities for Chester holiday rentals

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