Holiday rentals in Pittsfield

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Top-rated holiday rentals in Pittsfield

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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, 211 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
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5 out of 5 average rating, 121 reviews

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

Top guest favourite
A two-story building is featured, with a spacious balcony providing seating options. Large windows on the upper level allow ample natural light. The ground floor has two garage doors, and the exterior is finished in white siding, set against a backdrop of trees.
Guest suite in Pittsfield
4.97 out of 5 average rating, 34 reviews

Angel Mist Retreat Garage Apartment

Looking to get away from the hustle and bustle. You have found it! Watch for wildlife, while sipping coffee from the balcony of this cozy and stylish walkup apartment located in central Maine just minutes from I-95 between Augusta and Bangor. Ideal location for professionals, couples and parents traveling into Maine who enjoy solitude, but appreciate the comforts of modern amenities. Includes two king beds, stocked kitchen, large dining table, wifi, balcony off livingroom and master bedroom.

Top guest favourite
The exterior of the apartment is shown, featuring a wooden porch with steps leading to a front door. Colorful flower pots adorn the entrance, surrounded by well-maintained greenery and a grassy lawn. The building's siding is light grey, with multiple windows visible.
Flat in Pittsfield
5 out of 5 average rating, 20 reviews

Nice, Quiet & Comfortable Apartment.

3 room apartment. Sleeps up to 6 people with 1 shared spacious bathroom. Located in a quiet and safe neighborhood in Central Maine close to the highway. With everything you need for short or long term stays. Fully equipped kitchen, laundry room, TV, WiFi, parking for up to 4 cars. 1 mile away from Maine Central Intitute campus. Perfect location for snowmobiliers during the winter and tourists during the summer! 1 block away from the hospital and 2 minute drive to the grocery store.

Guest favourite
Cabin in Skowhegan
4.82 out of 5 average rating, 437 reviews

The Cabin -Skowhegan

Main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler. Loft has 2 twin beds. The couch could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large air fry oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/Blue ray player, Gas BBQ (May to November 1st.), as well as a picnic table, out door fire pit. For guest who are traveling by plane, towels are provided, upon request.

Top guest favourite
A view from a shaded patio showcases a round table surrounded by wicker chairs. The lush green lawn extends to the water's edge, where trees provide a natural frame for the serene expanse of the bay, dotted with clouds reflecting in the distance.
Home in Belfast
4.92 out of 5 average rating, 178 reviews

Belfast Ocean Breeze

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

Top guest favourite
A spacious living room features a large sectional sofa adorned with colorful cushions. A decorative area rug rests on hardwood flooring, complementing the light walls and artwork. A lamp emits soft light beside the sofa, while a potted plant adds a touch of greenery.
Home in Waterville
4.86 out of 5 average rating, 214 reviews

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Guest favourite
A dock and boat launch are visible on the waterfront, with a boat secured at the edge. A wooden picnic table is positioned on a deck, providing a space for relaxation and enjoyment of the serene lake view surrounded by trees.
Home in Hartland
4.9 out of 5 average rating, 30 reviews

Waterside Getaway

Come getaway at our waterfront house located in Hartland Maine. This is a perfect spot to unwind and enjoy the peaceful water while relaxing and having fun with your friends and family . A 30 min drive to downtown Waterville where you can find shopping and dining places for the whole family . Enjoy fishing , swimming and more right outside your door . The house also has a boat launch and dock for your boat if you choose to bring one. We hope you enjoy staying at our home.

Top guest favourite
A serene view of Raven Stone Farm showcases a large white building and a barn with a gray roof, surrounded by lush green lawns. Towering trees frame the scene, emphasizing the peaceful rural atmosphere. A gravel drive leads through the property, inviting exploration.
Farm stay in Palmyra
4.91 out of 5 average rating, 43 reviews

Quiet New England Farm

Raven Stone Farm is a quiet and picturesque farm nestled in Maine's beautiful Mid-Coast Region. Established in the early 1800’s, the farm offers Guests the chance to get away to the country in a cozy and comfortable setting, while being centrally located to all that Maine has to offer. Guests will have the camp like private "Barn Bunkhouse" to themselves with views of horses, deer, and wild turkeys. The farm is 2 miles from the town of Newport and Sebasticook Lake.

Guest favourite
The exterior of a log home is displayed, featuring a large green lawn and surrounded by trees. A covered porch with seating and a gas grill is visible. Sliding glass doors open to the rear of the house, providing access to the outdoor space.
Cabin in Canaan
4.93 out of 5 average rating, 163 reviews

Loon Lodge Canaan,ME

Escape to this charming 2,000+ sq. ft log home on Sibley Pond, just 30 mins from I-95. Perfect for up to 8 guests, it features an open living/dining area with vaulted ceilings and rustic décor. Enjoy a new dock, spacious front yard for lawn games, and scenic views. Nearby snowmobile and ATV trails offer year-round adventure. A peaceful retreat for families and friends to relax, explore, and make lasting memories.

Guest favourite
The kitchen features light-colored cabinetry and a large island with seating for four. A spiral staircase is visible, leading to the upper levels. Natural light is provided by windows above the sink and in the dining area, which includes a wooden table and chairs.
Flat in Pittsfield
4.89 out of 5 average rating, 112 reviews

Loft Retreat

Welcome to our enchanting loft retreat! Our thoughtfully designed apartment offers a serene escape with a touch of sophistication. Ascend the spiral staircase to discover a cozy bedroom complete with a work space and reading nook. Hidden up a trap door on the third level are two twin beds for the nimble. A full deck complete with a small fire pit is available in the warmer months. Your getaway awaits!

Top guest favourite
A charming ranch-style home features a front porch surrounded by lush green grass and mature trees. The exterior showcases a vibrant color, while large windows provide ample natural light. A clear blue sky enhances the inviting curb appeal of this comfortable retreat.
Home in Palmyra
5 out of 5 average rating, 66 reviews

The Gathering Place

The Gathering Place is a home away from home. This cozy 3 bedroom, 2 bath ranch on the river has direct ITS trail access. Park the trailer and ride the machines all the way to Greenville or take a slow paddle on the quiet river. Sit on the front porch and watch the world go by, Amish buggies to Maine logging trucks....you will see it all.

Popular amenities for Pittsfield holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Somerset County
  5. Pittsfield