Vacation rentals in Chester

4.94 out of 5 average rating, 179 reviews

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.

4.96 out of 5 average rating, 25 reviews

Place to stay in Lincoln

#1 Schlafman's Hollow Solar Cabins

Our cute off-grid 12x10 cabins are in a quiet woodland setting in Lincoln, Maine! 2 Adults per cabin maximum / NO kids. Not Mobility friendly. We include queen bed and bedding, towels, USB ports, 500 watt inverter, mosquito nets, communal areas include firepit, outdoor kitchen, event Outhouse with RV flush toilet and Little Buddy propane Heaters (May & Oct only). We ask that you provide drinking water, pack out your trash & bring your own firewood. Dog Park, Gift shops & Frisbie golf close!

4.76 out of 5 average rating, 37 reviews

Family Friendly lakefront cottage

Right on the water! You will be close to everything when you stay at this centrally-located cozy cottage directly on Mattanawcook Lake with breathtaking views, steps away from boat ramp, dock, and park, including beach, basketball courts and playground. One block away to Downtown Lincoln with restaurants and shopping. Relax on the porch or fish from the private dock (seasonal) /yard. Enjoy family time by the firepit. There is also a rowboat available for use. Off rt 95 / 45 mins from Bangor

5 out of 5 average rating, 76 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!

5 out of 5 average rating, 12 reviews

Tiny home in Howland

The Howland Hideout

Welcome to The Howland Hideout! This unique tiny home is the perfect getaway spot for all seasons, 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.

4.91 out of 5 average rating, 183 reviews

Cabin in Millinocket

Lakefront Log Cabin in Maine Woods

Welcome to Cole's Moosehorn Cabins & "The Way It Was"! Unplug & reconnect at this historic lakefront log cabin. Located on Northwest Pond, part of Seboies Lake, in T4R9, Maine just south of Millinocket. The cabin is rustic yet clean & comfortable. Take a paddle on our complementary canoes/kayaks & bask in views of the Chairback mountain range & Katahdin. Look for moose, enjoy the loons, stargaze & swim on this nearly private pond. cabin comes with everything you need and nothing you don't.

4.92 out of 5 average rating, 25 reviews

Home in Lincoln

19 Lake

Relax, Recharge, and Reconnect at 19 Lake on Mattanawcook! This freshly renovated rustic lake house sleeps 8 and offers the perfect mix of comfort, charm, and convenience. Centrally located in Lincoln, it’s just a short walk to restaurants, shops, and trails—while giving you private lakefront access, peaceful views, and cozy spaces to gather, cook, and unwind. Enjoy your morning coffee on the dock, afternoons by the water or under the maple tree, and evenings around the firepit under the stars.

5 out of 5 average rating, 24 reviews

Panoramic view lake cottage

Cottage with its own 175 feet of waterfront with panoramic views of a crystal clear spring-fed lake. Cottage has one bedroom/one bath plus full size futon in living room. Smart TVs in living room and bedroom. Washer and dryer in bathroom. AC. Linens, cable, WiFi, grill, 4 kayaks, 1canoe, and firepit provided. Floating dock and swim platform out in deeper water off shore. Located at end of quiet dirt road. Owner lives next door. Come to find your ideal mix of rest, relaxation and recreation.

4.98 out of 5 average rating, 85 reviews

Cottage in Brownville

Perfect Weekend Getaway at Schoodic Lake

The perfect weekend 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.

4.95 out of 5 average rating, 131 reviews

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

4.94 out of 5 average rating, 64 reviews

Apartment in Medway

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.

5 out of 5 average rating, 27 reviews

Guesthouse in Enfield

2 Bedroom Apartment on Cold Stream Pond

2 bedroom, 1 bath apartment over garage. Full kitchen. Access to Cold Stream Pond for both summer and winter recreation. Kayaks and some other items able to be enjoyed by guests. Sit back and listen to the distant waves of the water, the loons & wildlife, and the rustling leaves. Spend time in the summer along the shore front and on the lake, watch the breathtaking colors of fall, or experience winter wonderland on one of Maine’s most popular lakes for summer and winter recreation.

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Other great vacation rentals in Chester

Apartment in Medway

4.81 out of 5 average rating, 16 reviews

North Maine Apartment #2

JosephRating, 5 stars2 months ago

Great place for the price! The food at the cafe beneath is perfect for a quick meal before or after hiking.

5 out of 5 average rating, 41 reviews

Cabin in Sherman

Cedar Haven Mission LLC

WilliamRating, 5 stars6 days ago

Peggy and Wayne were gracious hosts- very friendly, communicative, and helpful. The space was immaculately clean, the cleanest Airbnb I've ever stayed in. They have thought of EVERYTHING you could possibly want/need in the space. Everything was so organized and neatly labeled. I would 10 out of 10 recommend this place! We had fun exploring the area's parks on bike, canoe, and hikes, all of which can be found in the helpful guide book Peggy put together. Thank you so much for having us!

4.76 out of 5 average rating, 62 reviews

Home with Sandy Beach On Cambolasse Pond

JayRating, 5 stars1 month ago

Tyler's place was AWESOME!! It was clean, cozy and quiet!!

4.94 out of 5 average rating, 67 reviews

Guest suite in Patten

The Loft: private studio suite on shared property

Mary CatherineRating, 5 stars5 days ago

Great place to stay whether it be for the night or a few days! Plenty to do in the area. Christopher was very friendly and responsive. Place was spotless. I would recommend staying here to any friend!

4.88 out of 5 average rating, 153 reviews

Cabin in Wytopitlock

Birch hill camp

AmyRating, 5 stars5 days ago

We stayed here for the weekend and it was perfect . Cabin is very comfortable and relaxing. Absolutely loved everything about it and will definitely stay here again.

4.96 out of 5 average rating, 51 reviews

Cabin in Weston

Beautiful Log Cabin near East Grand Lake, Maine

LynnetteRating, 5 stars1 week ago

Beautiful cabin. Great experience.