Title: The Best New Ashford, MA Chalets from $894 | Expedia.com [New Ashford Travel Guide](https://expedia.com/New-Ashford.dx183333)[Hotels in New Ashford](https://expedia.com/New-Ashford-Hotels.d183333.Travel-Guide-Hotels)[Vacation Rentals in New Ashford](https://expedia.com/New-Ashford-Vacation-Rentals.d183333.Travel-Guide-VacationRentals)[Car Rentals in New Ashford](https://expedia.com/Car-Rentals-In-New-Ashford.d183333.Car-Rental-Guide)[New Ashford Vacation Packages](https://expedia.com/New-Ashford.d183333.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=183333&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=183333&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=183333&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=183333&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for New Ashford chalets ![Exterior](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/84aaf038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/b9f89b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/062c285e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/w1200h799x0y1-17216d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Cropseyville [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) 10/10 Exceptional (3 reviews) "Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick H. $1,478 nightly $1,641 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/225c30fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ba39107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/c8edb36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ff859ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in Charlemont [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) 10/10 Exceptional (1 review) $800 nightly $894 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-01&endDate=2026-04-02®ionId=183333&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=APART_HOTEL) Cabins [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CABIN) Apartments [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=COTTAGE) Chalets [](https://www.expedia.com/Hotel-Search?destination=New+Ashford%2C+Massachusetts%2C+United+States+of+America®ionId=183333&latLong=42.605084%2C-73.239548&adults=2&startDate=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FNew-Ashford-Chalets.d183333-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNew-Ashford-Chalets.d183333-aaChalets.Travel-Guide-Accommodation) ## Top New Ashford Hotel Reviews ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Clean, quiet, and a great breakfast! The staff was friendly. We enjoyed a fire in our room and the free bottle of wine. " [](https://expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "I always sleep the best here. So quiet and comfortable. Love the lounge area. Bartender really nice. Had a lovely cheese plate. Shower is great. Great value!" [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 8/10 Good "The room is cozy and the kitchen is great. The pool area needs renovation but my kids still love the fact the pool is huge. Only downside is it takes forever to get your $150 deposit refunded:( every time and I leave the room spotless." [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 6/10 Okay "rooms have a weird smell, if the hotel is empty" [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "An ideal place to stay for a trip to The Clark Art Museum. Or Williams College. " [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. " [](https://expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "yes" [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Easy check-in; accommodating staff; clean room. Convenient but also quiet location." [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/3d1e6eef_y.jpg) ### Knotty Pine 10/10 Excellent "Cozy and Comfortable Room and Friendly Service. I am definitely reserving a room here again sometime soon! Awesome family owned business! Highly Recommend to anyone looking for a place to stay while traveling! " [](https://expedia.com/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ## Find out more about New Ashford ## New Ashford Chalets information | Number of reviews | 3 | | ----------------- | --------- | | Accommodation | 3 Chalets | | Lowest Price | $894 | | Highest Price | $1,641 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Brodie Mountain ](https://www.expedia.com/Brodie-Mountain-Hotels.0-l553248621532665538-0.Travel-Guide-Filter-Hotels) - [Hotels near Williamstown Theatre Festival ](https://www.expedia.com/Williamstown-Theatre-Festival-Hotels.0-l553248621532665542-0.Travel-Guide-Filter-Hotels) - [Hotels near Waubeeka Golf Links ](https://www.expedia.com/Waubeeka-Golf-Links-Hotels.0-l553248621561173643-0.Travel-Guide-Filter-Hotels) - [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - 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