Places to stay in Pittsfield

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Pittsfield

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Belfast

4.94 out of 5 average rating, 251 reviews

Gothic Victorian Carriage House Apartment

JosephRating, 5 stars5 days ago

Amazing place!! So many cool details throughout the space. Very inviting and loved the vibe. We really enjoyed all the thought clearly put into making this space so great. Really loved the bourbon welcoming tray, very cool. Would absolutely book the space again. My wife and I were able to walk to local restaurants and really enjoy town as well.

Top guest favorite

Guesthouse in Stockton Springs

5 out of 5 average rating, 29 reviews

The Cottage at Birch Hill

JenniferRating, 5 stars5 months ago

Hands down one of the best places I have ever been. Linda and Jay were so warm and welcoming. Homemade cookies, breakfast items, tea, coffee and snacks. Everything we could ever need. The home is beautifully decorated and immaculate! Linda and Jay were very proactive and thoughtful! They even left information books about the area, gave us some recommendations and answered all our questions. I wish we could have stayed longer! It was truly magical!

Guest favorite

Cabin in Kingfield

4.92 out of 5 average rating, 12 reviews

A place to be Twisted Branches Kingfield,Me

JohnRating, 5 stars1 week ago

If you need a little weekend getaway for yourself or you and your SO, this is your place. Tucked back in the woods is this cute little cabin you get all to yourself. Very peaceful and quiet. Cabin was cozy, charmful and practical. Highly recommend a trip if you are wanted to stay at a place close by Sugarloaf to get a few ski runs in. Great experience. Cheap accommodation. Highly recommend.

Top guest favorite

Treehouse in Brooks

5 out of 5 average rating, 13 reviews

Lakeview Tree-house

KatieRating, 5 stars5 months ago

Wow, this treehouse was just amazing! Toni was an excellent host and really made our stay special. The lake was beautiful and the treehouse was so cozy. Even in mid October this was a great trip. The lobster pound and Acadia National Park are must see’s along with the Belfast farmers market. Our friends will be hearing about this place!

Top guest favorite

Guesthouse in Islesboro

4.96 out of 5 average rating, 24 reviews

Milk House

AmyRating, 5 stars1 month ago

What a cute little bungalow. A one room wonder. Milk House was easy to get to and had a couple walks to ocean views. Right on the main road but very quiet. We were prepared for the limited kitchen & were able to make 3 fabulous dinners. Get ready to unwind & unplug.

Guest favorite

Apartment in Belfast

4.9 out of 5 average rating, 39 reviews

Hilltop Hideaway

CarolineRating, 5 stars1 month ago

The hosts were helpful when I needed assistance because they responded right away. The location was conveniently located because it was walking distance to downtown shops and activities. The unit was clean and free of clutter without a bad odor. The house itself was old and had a damp smell, but not their unit. It had a washer and dryer downstairs for all guests, which benefited me.

Vacation rentals for every style

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Hotels

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Unique stays

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Homes

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Popular amenities for Pittsfield places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Pittsfield's top sights

Bud's Shop 'n Save6 locals recommend

Vittles6 locals recommend

PopOnOvers5 locals recommend

J W Parks Golf Course5 locals recommend

Fogg Brook Resort - Golf Course5 locals recommend

Reny's Department Store4 locals recommend

Other great vacation rentals in Pittsfield

Top guest favorite

Cottage in Belgrade

5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago

This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!

Superhost

Home in Newcastle

4.91 out of 5 average rating, 32 reviews

Spring into the season eating lobsters w/friends

MarceloRating, 5 stars6 months ago

Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place

Top guest favorite

Cabin in Shirley Mills

5 out of 5 average rating, 30 reviews

Cabin 2 with bunk beds

GabeRating, 5 stars1 month ago

Absolutely beautiful and Julie is a lovely host! You have your own cabin, over looking a beautiful view with mountains. Julie told us how her husband built the cabins, and you can feel how much love was put into them. Definitely coming back!

Superhost

Home in Hartland

5 out of 5 average rating, 3 reviews

The Great Moose in Stunning Maine Swim, Fish & Ka

KevinRating, 5 stars7 months ago

My kids and I had an amazing time during our Labor Day weekend stay. The neighbors were so friendly and nice. The house was beautiful and had everything we needed. A market nearby for quick things. Beautiful area, access to water was great. We even got to enjoy the Harmony Free Fair and fireworks! Great weekend thank you!

Guest favorite

Cabin in Moscow

4.95 out of 5 average rating, 92 reviews

Cabins/Sporting camps-great location

EricRating, 5 stars6 months ago

This is a gem of a place. Very close to where we wanted to bird hunt. Access to ATV trails (be respectful and drive slow on access/shared roads). All that you need is in this place. We stayed in Cabin #1. As she mentioned just bring a towel and toiletries. We ate out all the time. Breakfast and lunch at Bingham General Store. Dinner at Patrick’s Pub one night, next night at Kennebec River Brewing. We’ll be back for sure.

Guest favorite

Cabin in Eustis

4.89 out of 5 average rating, 165 reviews

Brivera in the Mountains-20 min to Sugarloaf!

AlexandraRating, 5 stars1 week ago

Great place to stay! Everything was perfect for my group and felt very spacious. Great cabin to stay for a group Sugarloaf trip. Pro tip: Like the host describes, in the winter months be sure to drive an all wheel drive car. The driveway is uphill.

Guest favorite

Cabin in Belgrade

5 out of 5 average rating, 7 reviews

Great Pond Getaway|Lakefront|Dock|Sunset Views

ElizabethRating, 5 stars6 months ago

Wonderful weekend stay w our adult children. Kitchen had everything we needed to make dinner. Views of the lake were stunning. We all enjoyed a swim and paddle in the kayaks.

Superhost