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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Guest favorite

Home in Hartland

4.9 out of 5 average rating, 135 reviews

Lake front! Kayak/SUPs, Beach, Fire Pit, Game Room

-Lakefront Home w/ Flat Sandy Beach & Dock For Swimming & Fishing -Game Room w/ Air Hockey & Arcade Basketball -Large Deck & Patio To Hang w/ Family & Friends -Sit Around The Fire Pit, Enjoy The Brick Pizza Oven, Or BBQ On The Grill -5 Sleeping Areas, Fast Wifi, Sleeps 12 -Two Kayaks, Two Stand Up Paddleboards, A Pedal Boat, & Life Jackets Provided -90 Minutes To Acadia National Park or Portland -High Chair, Pack N' Play, & Linens, Towels, and Soaps Provided -Whole House Heating & A/C

Oct 3 – 10

G$104,179 GYD per night

Guest favorite

Cabin in Skowhegan

4.82 out of 5 average rating, 401 reviews

The Cabin -Skowhegan

This guest house, main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler bed. Loft contains 2 twin beds. There is also a couch that could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large toaster oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/blu ray player, Gas BBQ (May to November 1st.), as well as a picnic table, with benches and an out door fire pit and wood is supplied.

Dec 29 – Jan 5

G$23,257 GYD per night

Guest favorite

Apartment in Pittsfield

4.88 out of 5 average rating, 40 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. A small sleeper sofa is available as well for additional sleeping space. Your getaway awaits! Nearby: Maine Central Institute (.1 mi) Sebasticook Valley Hospital (1.3 mi) Hartland ATV Trail (.2 mi) Newport (8 mi) Unity (14 mi) Skowhegan (22 mi) Waterville (23 mi)

Oct 8 – 15

G$23,457 GYD per night

Guest favorite

Home in Thorndike

4.9 out of 5 average rating, 146 reviews

Rural spacious getaway with access for adventure

Newly-renovated house in the country. Quiet getaway, hunting basecamp, or a base for excursions around mid-coast Maine. Relax in this spacious home after enjoying nearby Unity, with train station and Amish community, or Belfast with its waterfront. Take day trips to Boothbay, Camden, Rockland, Bar Harbor, or Bangor. Or just enjoy nature on the back deck and nearby forest trails. Sleeps four in two formal bedrooms, two more adults on a futon, four/six kids or young adults in a rumpus room.

Nov 16 – 23

G$21,546 GYD per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Jan 17 – 24

G$20,515 GYD per night

Guest favorite

Apartment in Skowhegan

5.0 out of 5 average rating, 17 reviews

Cozy, cute, new, tiny duplex

Enjoy a stylish experience at this centrally-located place. This is one side of a duplex home, renovated from an early 1900’s little brick schoolhouse. It has a tiny home feel. Beautiful, original, historic maple wood floors mixed with a modern style. Gorgeous windows allow in natural lighting. Has a loft bedroom, full kitchen, and washer/dryer combo unit. Everything you need for a private night or weekend away. Walking distance to downtown and near the hospital. Private driveway.

Jun 13 – 20

G$26,818 GYD per night

Superhost

Home in Pittsfield

4.81 out of 5 average rating, 97 reviews

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!

Oct 4 – 11

G$39,338 GYD per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

G$17,153 GYD per night

Guest favorite

Cabin in Palmyra

4.97 out of 5 average rating, 37 reviews

Simple cabin with ample parking

Take it easy at this unique and tranquil getaway. Quick access off Route 2 and just minutes from Interstate 95. One room open concept cabin with a loft. 1 queen size bed in the loft, bunk twin beds down stairs, full bathroom with shower, full kitchen with pots/pans and utensils. Ladder to loft is just that, fairly steep and narrow. The address for this location is not recognized on maps. Directions will be provided. No wifi, no tv. Unplug and enjoy.

Feb 21 – 28

G$26,965 GYD per night

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 192 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

Oct 28 – Nov 4

G$20,515 GYD per night

Guest favorite

Cabin in Canaan

4.95 out of 5 average rating, 129 reviews

Loon Lodge Canaan,ME

30 minutes from I95 Enjoy beautiful Sibley Pond in a 2000+ square foot log home with plenty of space for 8 people! The home has numerous rustic decorations and a spacious open living/dining room with vaulted ceilings. Your family can enjoy the scenery, foliage, wildlife, pond and local snowmobile and atv trails. The property has a new dock and a large front yard perfect for lawn games and spending time with family and loved ones.

Nov 17 – 24

G$34,510 GYD per night

Guest favorite

Home in Unity

4.9 out of 5 average rating, 105 reviews

Unity Farmhouse ~ 4 br Victorian home 420 friendly

Unity Farmhouse is a big beautiful home right on Main Street, with 8 large rooms, two porches & a barn/garage on 1.5+ acres right near the center of the quaint town of Unity. Quick walk to Field of Dreams Park and Unity Pond. Unity is a great place to hike, bike, paddle, swim, skate, sled, & stargaze. Located on Maine's rural highway, Route 202, halfway between Augusta & Bangor. Unity Farmhouse is cannabis-friendly :)

Nov 21 – 26

G$32,624 GYD per night