90+ Vacation Rentals & Holiday Homes in Pittsfield |
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Pittsfield Accommodations - Hotels & Rentals

About Pittsfield Vacation Rentals

Discover More than 90 Incredible Getaway Rentals Available in Pittsfield. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Pittsfield.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Pittsfield, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Pittsfield. The Average Size of Places to Stay Near Pittsfield is 765.46 ft², with Prices Averaging US $289 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Pittsfield. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Pittsfield

Type Count
Vacation Homes 34
Cottages 14
Holiday Apartments 11

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Pittsfield with Online Reservations.

Weather in Pittsfield, ME

View the weather forecast for Pittsfield before booking your Pittsfield Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities PittsfieldGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World PittsfieldGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


JW Parks Golf Course
Northern Light Sebasticook Valley Hospital
Unity College
Colby College
Waterville Opera House
Skowhegan State Fairgrounds
Eaton Mountain
Hermon Mountain
Lake Wassookeag
Common Street Arts
Great Moose Lake
Sebasticook Lake
Redington Museum
Margaret Chase Smith Library
Lovejoy Pond
Sandy Pond
Fort Halifax
Inland Family Care
Community Spay and Neutor Mobile Clinic
DCI Clinic Fairfield

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


JW Parks Golf Course 82 Properties
Northern Light Sebasticook Valley Hospital 77 Properties

Frequently Asked Questions About Pittsfield?

What are the top hotels, lake houses & vacation rentals in Pittsfield?

We provide an array of great vacation destinations in Pittsfield. If you are looking to stay in or around the Pittsfield area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Pittsfield:

Which hotel, lake house, or vacation rental in Pittsfield is best for families?

Searching for a family-friendly getaway in Pittsfield? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Pittsfield?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 90 in the Pittsfield area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Pittsfield.


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