Waterfront holiday rentals in Chester

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chester

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

1 of 1 pages1 / 1

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

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

4.94 out of 5 average rating, 243 reviews

Guest favourite

A charming lakefront home showcases large windows and a spacious deck. The exterior features a mix of green siding and natural stone pathways, with a fire pit surrounded by seating. Nearby, seasonal foliage adds vibrant color to the serene landscape.

Home in Otis

Tranquil lakefront retreat for nature lovers

Lakefront home with gorgeous views of Springy Pond. Experience the best of Maine living! Enjoy four-season comfort in this home away from home! Idyllic Maine summers, breathtaking fall foliage, or a range of winter activities await. This beautiful house boasts private lake access and spacious grounds, making it a perfect location all year round. You can relax by the fire, or unwind in the hot tub as you create wonderful memories with friends and family. Nightly price includes service charges.

4.95 out of 5 average rating, 107 reviews

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

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!

5.0 out of 5 average rating, 107 reviews

Top guest favourite

Cottage in Millinocket

Lozier’s Lakefront, Fish, Swim, Campfire, repeat

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

4.92 out of 5 average rating, 189 reviews

Top guest favourite

A wooden dock extends out over tranquil waters, flanked by lush greenery. The water's surface reflects the calm sky, creating a serene atmosphere. Steps lead down from the dock to the gently lapping water, inviting relaxation and aquatic activities.

Cottage in Glenburn

Your own private getaway on Pushaw Lake!

Welcome to Pushaw Lake! You’ll find all the comforts of home here! :-) Come for the weekend! Save 20% for a week, or 30% for a month stay! :-) Jump in the lake or go on an adventure in a kayak or canoe this summer! Bring snowmobiles, snowshoes, skis, or go ice-fishing this winter! :-) Relax... Read a book and listen to the Loons, or sit around the fire pit and say goodbye to stress! :-) You’re less than 20 minutes from Bangor International Airport, Downtown Bangor, and UMO! :-)

4.95 out of 5 average rating, 260 reviews

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

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.

4.97 out of 5 average rating, 118 reviews

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

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.

4.94 out of 5 average rating, 222 reviews

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

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

4.95 out of 5 average rating, 180 reviews

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

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.

4.95 out of 5 average rating, 43 reviews

Guest favourite

A serene sunset over Schoodic Lake is captured through the silhouettes of trees. The sky displays warm hues of orange and pink, reflecting on the calm water surface, creating a peaceful scene. The horizon fades into a darker shade, enhancing the tranquility of the lake.

Guest house in Brownville

A Little Piece of Heaven

Our place is good for couples, solo adventurers, business travelers, and families (with kids). 3 night minimum. Cottage is located at 32 Lake Avenue, Brownville, Maine 04414. Turn right at A.E. Roberson's convenience store in Brownville, Maine onto Church Street. Follow Church Street for 4.7 miles and turn right onto Schoodic Lake Road. Follow Schoodic Lake Road for Approx. 4 miles. Bear right after crossing the railroad tracks and 32 Lake Ave. will be on your left at our mail box.

4.83 out of 5 average rating, 153 reviews

Guest favourite

A cozy living area features a combination of antique and modern furnishings. A blue armchair and maroon rocking chair are positioned beside a wooden desk. A flat-screen TV sits on a stand, facing a bookshelf filled with movies and books. Natural light filters through a window.

Home in Millinocket

Cottage Rental on Millinocket Stream - FAST Wi-Fi!

Welcome to our cozy, vintage home! A nearby walk offers access to shops, art galleries, restaurants, and playgrounds. The area offers many hiking opportunities, too, including the Appalachian Trail, Baxter Park, and Mt. Katahdin. Kayaking, fishing, and bird-watching available right from the yard, and swimming, moose tours, rafting, hunting, and snowmobiling are also nearby! The host, a state-registered Master Guide, is able to issue hunting/fishing licenses on-site (see "Other" heading).

4.73 out of 5 average rating, 321 reviews

Guest favourite

Cottage in Dover-Foxcroft

Charming, Year Round Lake Front Camp

We grew up spending our summers on Sebec Lake, and there's a reason the state motto is 'The Way Life Should Be'. This camp is lake front property, with outdoor seating, dining and swimming steps from the back door. The spacious layout of the camp provides the perfect family friendly escape any time of the year! In the winter there is plenty of ice fishing and snowmobile trails in the area, so it's the perfect place to share time with family and friends year-round!

4.96 out of 5 average rating, 100 reviews