Vacation rentals in Chester

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

Location · Family · Check-in

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

Location · Family · Decor

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!

Value · Family · Sleep quality

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.

Location · Family · Access

Family Waterfront Home with Cedar Barrel Sauna

Experience the beauty of Maine at our waterfront home perfect for up to 8 guests. Enjoy stunning water views from the screened porch, kids’ treehouse, and expansive dock. Explore with the provided kayaks, paddleboard, and canoe, unwind in the new cedar barrel sauna, or relax by the fire pit and listen to the loons. Cook on the 36-in. Blackstone grill. Close to Mt. Katahdin and Acadia Nat. Park. Swim, fish, ice skate, snowmobile—there’s something for everyone in this unforgettable setting.

Location · Family · Comfort

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

Family · Location · Walkability

Acadia Pines Cabin w/HotTub 10min2Downtown

Welcome to Acadia Pines Retreat, where the whispering pines and peaceful forest trails set the tone for your perfect Maine escape. Nestled just a short drive from Acadia National Park and the coast, this charming retreat offers the serenity of the woods with the comforts of home. * Peaceful, secluded location *Private hot spa jacuzzi to soak in after a day of hiking *Outdoor seating and stargazing spots 📍 Centrally located for day trips, lobster shacks, and scenic drives

Value · Family · Hiking

Luxurious and very private lake front cottage

This lakefront cabin is about 10 miles from Millinocket Maine and near Baxter State Park. Take it easy at this unique and tranquil getaway. The deck of this amazing property sits out over the beautiful waters of South Twin Lake. Spectacular views await you from both the inside and outside of the camp. This very private property consists of the entire peninsula. There is a large dock that is great for fishing, boating and swimming on the opposite side of the peninsula.

Value · Location · Grill

River front rustic cabin

Relax with an off-grid cabin secluded along the Penobscot river. This cabin has NO electricity,but is generator compatible. Guests may either bring their own generator or hosts have a generator available for rent (contact hosts for details). First tank of gas is free, will have to pay for additional fills. when coming to visit us you will travel a three mile dirt road, after which you will see the cabin nestled in the woods looking at the Penobscot.

Location · Family · Hospitality

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.

Value · Family · Indoor spaces

Grandma’s Cozy Cabin

Relax with the whole family at this cozy rustic cabin, that sits on 45 acres, surrounded by wildlife. If you’re looking to relax with nature this cabin is the place to stay. This cabin provides 2 private rooms each with queen beds, a loft that has a queen and a full beds. The ATV trail runs through the property and a short distance to ITS trails. Sit on the deck and relax and watch nature come to you.

Location · Family · Air conditioning

Field of Dreams Tiny Home

Escape to our charming tiny home near Bangor, a perfect retreat for 2. Enjoy serene field views from a panoramic window, a private hot tub, and a cozy fire pit. Inside, a modern wood-paneled interior with a projector screen for movie nights awaits. This unique stay offers tranquility and modern comfort, just minutes from the city.

Value · Family · Hiking