Vacation rentals in Pittsfield

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

Location · Value · Nearby

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

Family · Value · Amenities

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.

Family · Location · Hospitality

Spacious 2-Bedroom Downtown Apartment

This newly renovated second-floor apartment is in a very convenient location in the heart of Pittsfield. Close to schools, hospital, businesses, and I-95. Comfortably sleeps 4 guests in 2 tastefully decorated bedrooms. Located above a charming, quiet flower shop. Large windows throughout bringing bright, natural light with river views as the seasons change. Comforts include 1 queen-sized bed, 1 double bed, bedside charging ports, complimentary Wi-Fi, and coffee station. Washer & dryer on site.

Location · Family · Sleep quality

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.

Family · Location · Sleep quality

Acadia Pines Retreat HotTub-10 Min Downtown Bangor

Hot tub. Nature. Total peace. 🌲Acadia Pines Retreat-just 10 minutes from downtown Bangor and close to Acadia National Park. Warm wood ceilings, curated interiors, and cozy moments in the beautiful Maine woods. This retreat features open-concept living space styled with rich textures, soft lighting, and designer touches throughout. Sink into plush seating, enjoy slow mornings with coffee at the stone island, or unwind after exploring surrounded by stillness of forest in your private hot tub.

Value · Family · Decor

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.

Family · Location · Quiet

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.

Location · Family · Cleanliness

The Getaway- A Cozy Lakeside Cabin

Welcome to The Getaway, a charming lakeside rental on Lake Winnecook. Enjoy stunning waterfront views and sunsets from your cozy beachside cabin. With a heat pump to maintain comfortable indoor temperatures, high-speed business-class internet, and Roku TV, you'll have all the comforts of home. Your stay includes a private gas grill, fire pit, and kayaks. Join us at The Lodge and Cabins at Lake Winnecook for the perfect beach vacation in one of our lovely Maine cabins!

Value · Family · Heating

Cozy Waterfront Home With Breathtaking Views!!!

That's right, you're booking for an entire Waterfront home! Our home features a single floor with opened concept and one of a kind waterfront view. Rain or shine, the home offers a spectacular 180 view of nature that is breathtaking! Located in downtown Pittsfield, you are surrounded by all the amenities that you will need! Boating, fishing, hiking, golfing, parks, restaurants, skydiving, brewery, museum, library, farmer market, supermarket and many more to explore!

Location · Value · Sleep quality

Artist’s Loft

Welcome to the artist’s loft! Our thoughtfully designed apartment boasts original works from a local artist, providing a serene escape just minutes from I95. 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, private deck complete with a small fire pit is available in the warmer months. Your getaway awaits!

Location · Family · TV

Peaceful Escape for Work, Travel & Long stays

Welcome to your home away from home in Pittsfield, Maine. Ideal for traveling professionals, remote workers, healthcare staff, and extended stays, this quiet retreat offers reliable Wi-Fi, easy parking, a fully equipped kitchen, and all the comforts of home. Designed for low-friction living and comfort, it's the perfect place to work, relax, and settle in. Enjoy a peaceful small-town setting with modern amenities and long-stay comfort.

Location · Value · Hospitality