Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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

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Top guest favourite
A hot tub is positioned outdoors, featuring bubbling water and comfortable seating along the edges. It is surrounded by open gates, inviting guests to enjoy a relaxing soak. The setting is serene, with a natural landscape visible in the background.
Home in Northport
4.98 out of 5 average rating, 248 reviews

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Top guest favourite
Aerial view of a serene lakeside property surrounded by vibrant autumn foliage. The grassy area is complemented by the water's edge, showcasing a private dock extending into the lake. Various trees in warm colors enhance the natural beauty of the setting.
Home in Stetson
4.94 out of 5 average rating, 235 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

Guest favourite
Apartment in Pittsfield
5 out of 5 average rating, 11 reviews

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.

Top guest favourite
An aerial view of a spacious property surrounded by greenery, featuring a large house and an adjacent building. A swimming pool and a pond are visible in the backyard, integrating seamlessly with the natural landscape.
Guest suite in Pittsfield
4.98 out of 5 average rating, 42 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
Apartment in Pittsfield
5 out of 5 average rating, 25 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.

Top guest favourite
A rustic dining area features a small table with three wooden stools, positioned near a large window. The window offers a view of the water and outdoor space, framed by wooden shutters that complement the warm wooden walls.
Guesthouse in Newport
4.97 out of 5 average rating, 100 reviews

Cozy Bungalow

Only 25 minutes to Bangor medical facilities We added a cozy addition to our garage for guests to share our water front property. Your own private dock and small beach area Plenty of parking for your Utv or snowmobiles The Rail Trail is at the end of our driveway WiFi BBQ grill Washer and dryer Full-size fridge with freezer Picnic table Kayaks There is no stove to cook on inside, I am trying to avoid food smells inside. There is a new gas grill with side burner for outside cooking

Top guest favourite
Cabin in Kingfield
4.99 out of 5 average rating, 134 reviews

Cozy Cabin with Modern Amenities. Pet Friendly!

Kick back and relax in this beautifully renovated home with amenities you didn't know you were missing. Despite its small stature, every square inch is utilized, boasting 4 beds and 1.5 bathrooms, including a huge shower with multiple shower heads and hurricane force water pressure. Located on a quiet street just minutes from the Kingfield village, steps from the snowmobile trail system, and 20 minutes from Sugarloaf. Designed with dogs in mind, complete with a fenced in backyard.

Superhost
Cabin in Glenburn
4.78 out of 5 average rating, 117 reviews

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

Top guest favourite
A private hot tub, designed for four people, is filled with bubbling water and situated just outside a residential home. A door can be seen leading into the house, and colorful outdoor seating is positioned nearby on gravel.
Home in Brooks
4.98 out of 5 average rating, 143 reviews

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

Top guest favourite
Cabin in Jackson
4.99 out of 5 average rating, 204 reviews

Forest Cabin with Wall of Windows

Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

Top guest favourite
A private therapeutic hot tub is situated on a spacious deck, surrounded by lush trees and a serene natural landscape. Nearby, a gas grill is positioned for outdoor cooking, complementing the tranquil ambiance of the outdoor space.
Yurt in Appleton
4.95 out of 5 average rating, 370 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Guest favourite
Apartment in Pittsfield
4.89 out of 5 average rating, 127 reviews

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!

Popular amenities for Pittsfield vacation rentals

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