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 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
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
4.95 out of 5 average rating, 225 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
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
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

Guest favourite
A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.
Cottage in Hermon
4.91 out of 5 average rating, 141 reviews

Lakefront Cottage on Tracy Pond

Lakefront cottage on 47 acre Tracy pond. The pond has no public access so it is quiet with only my home and another Air BnB on site. You share the backyard with my home. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

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.

Superhost
A rustic red cabin features a sloped metal roof and large windows, inviting natural light inside. A gravel path leads to the front door, which is flanked by a porch area. Surrounding trees, adorned with autumn leaves, provide a colorful backdrop.
Cabin in Millinocket
4.88 out of 5 average rating, 8 reviews

East Smith Pond Camp

This lakefront cabin is about 5 minutes from Millinocket, Maine and near Baxter State Park. The deck outside and four season porch both overlook the beautiful waterfront westerly sunset views of Smith Pond.This waterfront property has a sandy beach , great for swimming ,kayaks and very good fishing with fire pit for relaxing . The inside has two bedrooms, one with a queen bed and the other with a twin bed. There is a loft bedroom accessible with ladder access that also has a full size bed.

Top guest favourite
A single-story duplex in a natural setting is showcased, featuring a light beige exterior. Symmetrical black shutters frame the large front windows. The entry is marked by a set of white double doors, leading to a welcoming atmosphere. Lush green grass surrounds the property.
Home in Enfield
5 out of 5 average rating, 37 reviews

The Hidden Oasis, UNIT A

Whether you're seeking a peaceful retreat or an adventurous getaway, our 2 bed, 1 bath, duplex (side A) Airbnb in Maine offers the perfect haven to create cherished memories making it an ideal accommodation for up to 6 guests. Outside, you can sit and relax and enjoy the pleasant weather on our beautiful outdoor seating area on the patio, complete with a mesmerizing fire pit. Our Airbnb is close to trails, lakes, beaches, hiking spots, fishing spots, shopping, restaurants etc.

Top guest favourite
A serene lakeside scene features a wooden dock extending over calm waters, framed by tall trees. A stone fire pit is situated on the shore, and neatly stacked firewood is visible nearby. The sky transitions to soft pastel colors at sunset, reflecting on the lake.
Cottage in Millinocket
4.92 out of 5 average rating, 170 reviews

Lozier’s Lookout- Lakefront, Millinocket Lake

Lozier’s Lookout is a cozy two-bedroom, lakefront cottage on beautiful Millinocket Lake. Perfect for both adventure and relaxation, guests can enjoy nearby hiking, biking, ATV'ing, and local dining, or stay close to home casting a line off the dock, swimming in the lake, paddling the provided kayaks or canoe, and gathering around the campfire for s’mores. With the charm of a classic cabin and the comforts of home, The Lookout offers a welcoming retreat in every season.

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.

Popular amenities for Chester holiday rentals

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