--- title: "The Best 5 Star Hotels in Pittsfield, MA from $88 | Expedia" description: "Save on luxurious 5★ hotels in Pittsfield: Browse our selection of popular hotels & resorts in the region, providing top-notch amenities. Book an outstanding vacation with Expedia." canonical: "https://www.expedia.com/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels" language: en-US market: US currency: USD prices_as_of: 2026-11-14T21:26:00Z --- Plan your trip - [Pittsfield Travel Guide](https://www.expedia.com/Pittsfield.dx9478) - [Hotels in Pittsfield](https://www.expedia.com/Pittsfield-Hotels.d9478.Travel-Guide-Hotels) - [Flights to Pittsfield](https://www.expedia.com/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights) - [Car Rentals in Pittsfield](https://www.expedia.com/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide) - [Pittsfield Vacation Packages](https://www.expedia.com/Pittsfield.d9478.Destination-Travel-Guides) - [Vacation Rentals in Pittsfield](https://www.expedia.com/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals) # Find 5 Star Hotels in Pittsfield, MA from $88 ![A historic building with a clock, a flag, and a street lamp.](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates [Check prices for these dates, December 14 – 15, 2026](https://www.expedia.com/Hotel-Search?regionId=9478&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&star=50) [View in a map](https://www.expedia.com/Hotel-Search?regionId=9478&stayLength=1&daysInFuture=30&pwaOverlay=map) ## Top Pittsfield Hotel Reviews ### [Hotel On North](https://www.expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![A building entrance with a large planter with purple flowers and a small tree.](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Pittsfield - Review: The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and..., by Steve, February 28, 2016, rated 10/10 Excellent ### [Devonfield Inn B&B](https://www.expedia.com/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lee - Review: The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!, by Anonymous traveler, January 20, 2019, rated 10/10 Excellent ### [Prospect Berkshires](https://www.expedia.com/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Egremont - Review: So fantastic!! The cabins are gorgeous and very well appointed. We are going back!, by Emily, July 7, 2025, rated 10/10 Excellent ### [Inn at Silver Maple Farm](https://www.expedia.com/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) ![A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/f2737e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: East Chatham - Review: This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!, by Michelle, March 7, 2022, rated 10/10 Excellent ### [Element by Marriott Lenox Berkshires](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lenox - Review: Clean and spacious room., by Richard, November 12, 2026, rated 10/10 Excellent ### [Harbour House Inn](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Cheshire - Review: The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended., by Anonymous traveler, June 26, 2017, rated 10/10 Excellent ### [The Inn at Stockbridge](https://www.expedia.com/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Stockbridge - Review: Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌, by Kevin, February 19, 2024, rated 10/10 Excellent ### [Shaker Mill Inn](https://www.expedia.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![A red building with a sign reading "Shaker Mill Inn."](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: West Stockbridge - Review: This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to..., by Joe, February 27, 2022, rated 10/10 Excellent ### [Chambery Inn](https://www.expedia.com/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![A two-story building with a sign reading "Chambéry Inn".](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lee - Review: The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls. Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance., by Elaine, June 22, 2016, rated 10/10 Excellent ### [Brook Farm Inn](https://www.expedia.com/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) ![A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lenox - Review: We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!, by roberta, January 8, 2024, rated 10/10 Excellent ### [Hilton Garden Inn Lenox Pittsfield](https://www.expedia.com/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b3b1ec3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Pittsfield - Review: The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was, by t, January 18, 2016, rated 10/10 Excellent ### [The Yankee Inn](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Two Adirondack chairs facing a river with a forested hill in the background.](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/a4d29137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lenox - Review: We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!, by Colleen, July 17, 2024, rated 10/10 Excellent ### [The Cornell Inn, Lenox & The Berkshires](https://www.expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![A snow-covered outdoor area with a patio, seating, and a covered dining area.](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Lenox - Review: VERY friendly staff and location for area attractions., by Lawrence, February 12, 2023, rated 10/10 Excellent ### [Little Cat Lodge](https://www.expedia.com/Hillsdale-Hotels-Little-Cat-Lodge.h94739508.Hotel-Information) ![A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/b5bb1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Copake Falls - Review: I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay., by Elisabeth, April 6, 2025, rated 10/10 Excellent ### [Maple Terrace Motel](https://www.expedia.com/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![A garden with a swing set, a blue chair, and a flower bed.](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Williamstown - Review: Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates., by Eric, May 2, 2024, rated 10/10 Excellent ## Find out more about Pittsfield You enjoy the finer things in life, both at home and on vacation. Add even more pleasure on your next trip to Pittsfield by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. There's no reason to delay a getaway to Pittsfield any longer. You'll join the multitudes of vacationers who have made Pittsfield so fashionable recently. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. What are you waiting for? Reserve one of our 5-star hotels in Pittsfield and indulge in the finer things in life for a while. ### Book the Best Pittsfield 5-Star Hotels Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Michelin-starred restaurants, concierges, and in-room massages are all at the ready. You're sure to find exactly the accommodation you need. We should also mention, the hotels in this area receive fantastic marks for customer satisfaction, so you know you'll be well cared for during your getaway. How do you want to relax? A concierge to help you make reservations at that outstanding restaurant? A deep-tissue massage to help your cares fall away? High thread-count sheets, delectable chocolate desserts, and even spectacular views...these hotels will leave you amazed. Want to see for yourself? Then check out the many reviews left by previous guests -- you can take their word for it! But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Pittsfield are waiting for you to relax after a busy day. ### Make Your Escape The results are in, and Pittsfield 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Select one of our Pittsfield 5-star hotels today and settle down in the lap of luxury tomorrow. ## Frequently Asked Questions ### How much does it cost to stay in a 5-star hotel in Pittsfield? How much you pay for a 5-star hotel in Pittsfield depends on factors such as when you plan to go and the length of your break. A top tip for scoring the best deal? Use our pricing filters to check out all of the available hotels for your preferred dates. - Search for the lowest price per night from $88 ### What makes a hotel 5 stars in Pittsfield? In Pittsfield, a hotel must provide a certain number of upscale features to be designated 5 stars. These may include saunas and spas, on-site gyms, gourmet restaurants, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their extraordinary service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may also offer additional touches such as a welcome gift. ### Are there any 5-star all-inclusive resorts in Pittsfield? Find an upscale retreat that includes your lodging, meals, drinks and entertainment in Pittsfield with the help of our filter tool. Search for properties rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the purchase price. This way, you'll be ready to maximize all the perks on offer as soon as you arrive. ### Are there any 5-star vacation rentals in Pittsfield? Although there aren't any 5-star vacation rentals in Pittsfield on our site, we have a range of retreats that promise a memorable getaway. Find one that matches your style by checking out our [vacation rentals in Pittsfield](https://www.expedia.com/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals). ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Hotels near Berkshire Museum](https://www.expedia.com/Berkshire-Museum-Hotels.0-l553248621532665288-0.Travel-Guide-Filter-Hotels) - [Hotels near Berkshire Athenaeum](https://www.expedia.com/Berkshire-Athenaeum-Hotels.0-l553248621532665287-0.Travel-Guide-Filter-Hotels) - [Hotels near Colonial Theater](https://www.expedia.com/Colonial-Theater-Hotels.0-l553248621532665289-0.Travel-Guide-Filter-Hotels) - [Hotels near Barrington Stage Company](https://www.expedia.com/Barrington-Stage-Company-Hotels.0-l553248621532665294-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Berkshire County](https://www.expedia.com/Berkshire-County-Cabins.d553248635083901436-aaCabins.Travel-Guide-Accommodation) - 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[Flights from Ontario (ONT) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/ont/psf/ontario-to-pittsfield) - [Flights from Cincinnati (CVG) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/cvg/psf/cincinnati-to-pittsfield) - [Flights from Burlington (BTV) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/btv/psf/burlington-to-pittsfield) - [Flights from New Haven (HVN) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/hvn/psf/new-haven-to-pittsfield) - [Hopscotch Air Nantucket (ACK) to Pittsfield (PSF) flights](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-nantucket-memorial-to-pittsfield-municipal/o2/ack/psf) - [Flights from Reno (RNO) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/rno/psf/reno-to-pittsfield) - [Flights from Tucson (TUS) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/tus/psf/tucson-to-pittsfield) - [Flights from Louisville (SDF) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/sdf/psf/louisville-to-pittsfield) - [Flights from Newburgh (SWF) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/swf/psf/newburgh-to-pittsfield) - [Hopscotch Air Burbank (BUR) to Pittsfield (PSF) flights](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-hollywood-burbank-to-pittsfield-municipal/o2/bur/psf) - [Flights from Barcelona (BCN) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/bcn/psf/barcelona-to-pittsfield) - [Flights from Des Moines (DSM) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/dsm/psf/des-moines-to-pittsfield) - [Flights from El Paso (ELP) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/elp/psf/el-paso-to-pittsfield) - [Flights from Dayton (DAY) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/day/psf/dayton-to-pittsfield) - [Flights from Oakland (OAK) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/oak/psf/oakland-to-pittsfield) - [Flights from Fort Myers (RSW) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/rsw/psf/fort-myers-to-pittsfield) - 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[Flights from St. Petersburg (PIE) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/pie/psf/st-petersburg-to-pittsfield) - [Flights from Kuwait City (KWI) to Pittsfield (PSF)](https://www.expedia.com/lp/flights/kwi/psf/kuwait-city-to-pittsfield) - [Hopscotch Air Lewisburg (LWB) to Pittsfield (PSF) flights](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-greenbrier-valley-to-pittsfield-municipal/o2/lwb/psf) - [Hopscotch Air Williamsport (IPT) to Pittsfield (PSF) flights](https://www.expedia.com/lp/flight-routes/hopscotch-air-from-williamsport-regional-to-pittsfield-municipal/o2/ipt/psf) - [Berkshire Museum](https://www.expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) - [Berkshire Athenaeum](https://www.expedia.com/Berkshire-Athenaeum-Pittsfield.d553248621532665287.Vacation-Attraction) - [Canoe Meadows Wildlife Sanctuary](https://www.expedia.com/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Herman Melville's Arrowhead](https://www.expedia.com/Herman-Melvilles-Arrowhead-Pittsfield.d553248621532665284.Vacation-Attraction) - [Car rental Pittsfield Airport (PSF)](https://www.expedia.com/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ es: https://www.expedia.com/es/5Estrellas-Pittsfield-Hoteles.s50-0-d9478.Guia-Viajes-Filter-Hoteles en-CA: https://www.expedia.ca/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels th-TH: https://www.expedia.co.th/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels ar: https://www.expedia.sa/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels ja-JP: https://www.expedia.co.jp/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels en-IN: https://www.expedia.co.in/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels zh-CN: https://www.expedia.com/cn/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels en-AE: https://www.expedia.ae/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels en-TW: https://www.expedia.com.tw/en/5Star-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels id-ID: https://www.expedia.co.id/Bintang5-Pittsfield-Hotels.s50-0-d9478.Travel-Guide-Filter-Hotels ```