Title: TOP Luxury Hotels in Ashuwillticook Rail Trail, MA for 2026 - Ashuwillticook Rail Trail Upscale Hotels | Expedia.co.uk [Ashuwillticook Rail Trail Travel Guide](https://expedia.co.uk/Ashuwillticook-Rail-Trail.dx811531152953708544)[Hotels in Ashuwillticook Rail Trail](https://expedia.co.uk/Ashuwillticook-Rail-Trail-Hotels.d811531152953708544.Travel-Guide-Hotels)[Holiday Rentals in Ashuwillticook Rail Trail](https://expedia.co.uk/Ashuwillticook-Rail-Trail-Holiday-Rentals.d811531152953708544.Travel-Guide-HolidayRentals)[Flights to Ashuwillticook Rail Trail](https://expedia.co.uk/Cheap-Flights-To-Ashuwillticook-Rail-Trail.d811531152953708544.Travel-Guide-Flights)[Ashuwillticook Rail Trail Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Ashuwillticook-Rail-Trail.d811531152953708544.Car-Hire-Guide)[Ashuwillticook Rail Trail Holidays](https://expedia.co.uk/Ashuwillticook-Rail-Trail.d811531152953708544.Holidays-City-Breaks) ![The Ashuwillticook Rail Trail](https://images.trvl-media.com/place/811531152953708544/1c2ab733-2998-46b6-94e0-15c0716f2da6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/811531152953708544/1c2ab733-2998-46b6-94e0-15c0716f2da6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Ashuwillticook Rail Trail Luxury Hotels Tonight [3 Feb - 4 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=811531152953708544&startDate=2026-02-03&endDate=2026-02-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [4 Feb - 5 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=811531152953708544&startDate=2026-02-04&endDate=2026-02-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [6 Feb - 8 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=811531152953708544&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [13 Feb - 15 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=811531152953708544&startDate=2026-02-13&endDate=2026-02-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Ashuwillticook Rail Trail luxury hotels ![Front of property – evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/30e56504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (572 reviews) "Great stay. Comfortable hotel and very friendly staff. Restaurant is very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica £152 includes taxes & fees 4 Mar - 5 Mar [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/870ad54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.co.uk/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (291 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny £123 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #10 Queen's Cottage | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.co.uk/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (135 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.co.uk/Lee-Hotels-Devonfield-Inn-BB.h1575232.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) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/88348850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/b5bad44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/c5b973e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) Lee 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £205 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/a1fa9bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/e72452e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/17ba6dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/2cf52cb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Four Chimneys Inn [](https://www.expedia.co.uk/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) Bennington 9.4/10 Exceptional (281 reviews) "This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy [](https://www.expedia.co.uk/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah £274 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/a093eeea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.co.uk/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (355 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn £81 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Library](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/2785b1e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/2c4f0bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/7038eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/84448130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Shire [](https://www.expedia.co.uk/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) Bennington 9.0/10 Wonderful (122 reviews) "A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. would definitely stay here again." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) TROY £162 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.co.uk/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £328 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/f5dca788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby £179 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.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.co.uk/Hotel-Search?startDate=2026-02-17&endDate=2026-02-18®ionId=811531152953708544&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Ashuwillticook Rail Trail Hotel Reviews ![The Little Lion](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef_y.jpg) ### The Little Lion 10/10 Excellent "Great friendly staff" [](https://expedia.co.uk/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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 "Comfy cozy " [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Great staff, beautiful hotel. Would definitely recommend " [](https://expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Nice location and beautiful lobby. " [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. " [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Very satisfied with our stay here. The property is comfortable and quiet, pet friendly and included both a jetted tub and a sauna in the room. The front desk staff was excellent and very friendly. Lots of dining options and shopping close by too. Would definitely stay here again next time we're in town. " [](https://expedia.co.uk/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would love to stay here again. My kids said this is their favorite hotel we have ever stayed at which is high praise since we travel frequently and have stayed in a ton of hotels!" [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [5 Star Hotels in Cheshire ](https://www.expedia.co.uk/5Star-Cheshire-Hotels.s50-0-d6005398.Travel-Guide-Filter-Hotels) - [Adams Hotels ](https://www.expedia.co.uk/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [Hotels near Animagic Museum of Animation ](https://www.expedia.co.uk/Animagic-Museum-Of-Animation-Hotels.0-l553248621560926701-0.Travel-Guide-Filter-Hotels) - [Becket Hotels ](https://www.expedia.co.uk/Becket-Hotels.d6005395.Travel-Guide-Hotels) - [Gay-Friendly Hotels in Cheshire ](https://www.expedia.co.uk/Cheshire-Hotels-Gay-Friendly-Hotel.0-0-d6005398-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Cheshire Hotels ](https://www.expedia.co.uk/Cheshire-Hotels.d6005398.Travel-Guide-Hotels) - [Dalton Hotels ](https://www.expedia.co.uk/Dalton-Hotels.d6911.Travel-Guide-Hotels) - 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