Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
A modern post and beam house is set against a backdrop of trees. The exterior features large glass windows that enhance natural light. A spacious deck with railing is visible, providing an outdoor space for relaxation.
Home in Millinocket
4.98 out of 5 average rating, 116 reviews

Rice Farm Hideaway; A little slice of heaven.

This sweet post & beam house is located near town yet private and tucked away in the woods, cozy & comfortable, pet friendly, close to ATV & snowmobile trails, and Baxter State Park, Katadhin Woods and Water, plus numerous lakes and the beautiful Penobscot River. The house can comfortably sleep up to 6 people. The living area is open and sunny with a big kitchen. There is plenty of parking for recreational trailers. Come enjoy a rewarding climb up Katahdin or grab a book and read on the deck.

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, 113 reviews

Sled/Ice Fish/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.

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, 160 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

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
A historic covered bridge is depicted, nestled in a snowy landscape. Tall trees with bare branches frame the image, while a gentle river flows beneath the bridge, partially frozen. The bright blue sky enhances the serene winter scene.
Flat in Sangerville
4.84 out of 5 average rating, 196 reviews

Rustic Country Apartment on The Moosehead Trail.

We recently acquired the house we live in which has an efficiency apartment in the back. It is cozy and private. The house is old and unique. It was previously a long term rental. We wanted to provide a restful space in the heart of Maine Highlands, the crossroads of Central Maine. We enjoy the scenic area with beautiful lakes rivers, multiuse trail systems and trail head of the 100 mile wilderness of the Appalachian Trail, Moosehead lake, Maine's largest lake, and State Parks.

Superhost
A cozy living area features a dark sofa complemented by plush cushions, flanked by two comfortable armchairs. A low coffee table stands atop a soft area rug, while natural light streams through two windows, providing a bright and inviting atmosphere.
Flat in Millinocket
4.77 out of 5 average rating, 116 reviews

"The Last Hike" Downtown Millinocket

PLEASE READ ALL THE DETAILS OF OUR LISTING. 3rd floor, converted attic "Penthouse" apartment is steps away from Downtown Millinocket and all your outside adventures: fishing, snowmobiling, skiing, white water rafting, biking, etc. Close access to snowmobile trails, 2 minute walk to downtown/Marathon, close to Katahdin and Baxter State Park. Can't promise you will see a rainbow out our window, but on a clear day, when the leaves have fallen off the trees, you can see Katahdin!

Guest favourite
The kitchen features a central island with seating for two, highlighted by a pendant light overhead. Equipped appliances include a microwave, coffee maker, and a stove. Colorful patterned curtains frame the window, adding a touch of charm to the functional space.
Flat in Millinocket
4.92 out of 5 average rating, 417 reviews

Near Downtown Apartment

Two bedroom second floor apartment! Chalkboard wall, (with art and signatures from guests all over the world since 2018 dont forget to sign the wall) two tv’s (master bedroom and LR) with Netflix, Hulu, + access, and high speed internet! Owner occupied building. Street next to downtown, hiking trails, and snowmobile trails! We are not near a lake, no idea why airbnb did that and can not change it. We are near a river that many take kayaks and canoes out onto.

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, 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.

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
4.76 out of 5 average rating, 76 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.

Guest favourite
The cabin's exterior features a rustic wooden facade with large windows framed by greenery. A small front porch with steps leads to the entrance. A gas grill is situated nearby, set against the backdrop of surrounding trees and open grass.
Cabin in Wytopitlock
4.88 out of 5 average rating, 163 reviews

Birch hill camp

Modern cabin w/power, water. 3 bunk beds in one large bedroom,sleeps 6. Outside firepit. Miles of woods via logging roads to explore moose, deer, bird watching, hunting. Fishing for trout bass/perch. Guided hunting, fishing, and canoeing available, ponds and rivers. Canoes maybe available. X skiing and snowshoeing Trail from camp to ITS snowmobile trail 1/2 mile. Bed linen/light blanket provided. Towels not provided

Top guest favourite
A modern kitchen features white cabinetry with ample counter space. Stainless steel appliances are present, including a stove and microwave. A window allows natural light, while decorative elements, such as a wall hanging and greenery, add character to the space.
Home in East Millinocket
4.97 out of 5 average rating, 149 reviews

Spruce Street Retreat

Clean and cozy home in a quiet residential neighborhood, about 30 miles away from Baxter State Park. It's just a few blocks away from the snowmobile and atv trails and only a couple of miles off I-95. I cannot accept pets at this time, including service animals. I have an exemption for this because of my severe allergies to cats and dogs.

Popular amenities for Chester holiday rentals

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