Title: Luxury Vacations in The Berkshires 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Luxury Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Photo courtesy of Berkshire Visitors Bureau Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Plan the perfect luxury The Berkshires vacation with Expedia #### What are some benefits when booking luxury The Berkshires vacations? When you book a luxury The Berkshires vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in The Berkshires? If you're looking for something luxurious in The Berkshires, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from , there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to . After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in The Berkshires. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in The Berkshires? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout The Berkshires. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in The Berkshires. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in The Berkshires? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of The Berkshires or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in The Berkshires. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Luxury Hotels in The Berkshires ![The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood 26 Glendale Road, RR 183, Stockbridge, MA - 12 min drive from Tanglewood Music Center Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ... 9.2/10 Wonderful! (82 reviews) My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ... Reviewed on Oct 12, 2025 [](https://expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![The Orchards Hotel](https://images.trvl-media.com/lodging/1000000/10000/8800/8739/9f24830b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Orchards Hotel 222 Adams Rd, Williamstown, MA - 59 min drive from Tanglewood Music Center Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Colonial Plaza and Linear ... A little dated. Restaurant shut down for renovations, disappointing Reviewed on Mar 9, 2020 [](https://expedia.ca/Williamstown-Hotels-The-Orchards-Hotel.h8739.Hotel-Information) ![Lantern House Motel](https://images.trvl-media.com/lodging/12000000/11540000/11537600/11537599/74a22cf7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lantern House Motel 256 Stockbridge Road, Great Barrington, MA - 24 min drive from Tanglewood Music Center Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ... Avoid staying here if you can. The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ... Reviewed on Nov 22, 2021 [](https://expedia.ca/Great-Barrington-Hotels-Lantern-House-Motel.h11537599.Hotel-Information) [See all 1,105 properties in The Berkshires](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6047665) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Luxury Vacation Destinations > - [Luxury vacations in Portugal](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/147/Portugal) > - [Luxury vacations in India](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Hotels](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[The Berkshires Vacation Rentals](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacations](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAE1klEQVR4Xu3bTW7jOBBAYRq98HKOoKPkaNLRfBQfYZZeBF2T+hGLohUDhUbPIn5vk7ia5KcdI3TS5H+ozYO/EUgpkFIgpUBKgZQCKQVSCqQUSCmQUiClQEqBlAIpBVIKpBRIKZBSIKVASoGUAikFUgqkFEgpkFIgpUBKDchnm1p0urV/5HcMhlUXkdu+6mu0yr+xprfmySAgICDeolMQEJAJWfOTBCK+/UMe+qWfaMjVF+SodzwLBAQERAPJUQ8EJNZaV0fOTzypr7JiYw9kCgSkgYBEIFMgsbZ9vWJLIHFiZNe+yF2/BwFpICARSAMBaX+GWDaKE8f6iRbI4nOQXAkiICAWyOJzkFw5I1ls3/yOlx359HOm9Okufet8FsgUCIgFAiIgT70ncmzxtbb91q7ufj+aWvNkkJPR1Jong5yMptY8GeRkNLXmySAno6k1TwY5GU2teTLIyWhqzZMH5Ltyu34aH2VEXgUC8l0gGQjId4FkPxmxP2Wy7a390lfs+FOma18Rb90xuuvCdf+3h35a9k8RiIB4IB4ISAYiIPOJd0U0c8fi743tURbfOP4Jct8YgYAIiG0EAQGZAomX51yr2+Pl+bf+fpdl27dmjxL1UYvfAot0YwQCAgLigXi6MQIBGZGrDsbtfWTlKv1iq55GQyAgICAgIJudmiPr6cS3RvpVHduth788t35733xNrIpr31bZWbFKAxEQ3QDSQED8rFilgcjbI+In7kg/MX6X2lp8nY26G48yPd0QCIiAgICAgAwdEc3WfhUnbi1ubxtZ6lrXmA+rDFn63AMBiUBA9AvIGAiIHE8UufuJ6cZIu+i1H0i8m1uGWLoxAgEREBDrvq8F2QMB+RxOtLWLj+xCt1Gs0hKxV2wZrv2+sQcCAgICAgLyCsm1ur0dEe2X/yRgI91/eBQrT9wDsZHuB2kgXp64B2Ij3Q/SQLw8ce+nItpFv88TZXD9m72jO/4Hc7g9kAbiW0BAQEBArAGJ9rUid92w+vSmiI7CtUexbFVzpGereiAgEQiILl99CmKBgNgdP66Nqzru+Hbq6qoon24ORED0ABABAXkKRED8xItutxNjZPUT7VHsRdxWdSQe5eqfjoGAgPgCEJCnQEDyRCu2b37tf/jIXp51ZD384HjrbnHHR6uvsX35LQiIBgICsgdigeTamG4tL/RcO7jLMB1/ElhzDAICMkxBQEBAJmQuL3TbHqv0US6xad4Rq46BgIAcAgHJQEBOCjdPXHxkruhPAtHqg3iUuz7dEIgFcgwERAMBsd4aiRMzO1Ev9Bbv07FqlXzF1hObr7ooEhuPgYCA6D+DgNjGYyAgsX0v1m4t/4M5Tow7vp+YG2PUXt7xa34C8UCsu58BAgLigVjvgtiF3trVkU/9PpBH377FSd+kjwICIiAvAwGJQF701oiOLvvig9tXibr5KP2sHggIiP4LCAgIyN5rRHy7ldu1S7xP993WzTdaa45BQECGQEBAQJ6QLBBx92Mfv0TsUUBAIhAQkEMgIDk8IscWnW7+/YdvX3zV+IrdM9dGtnEIBARkD0RAjoGA/L1ASoGUAikFUgqkFEgpkFIgpUBKgZQCKQVSCqQUSCmQUiClQEqBlAIpBVIKpBRIKZBSIKVASoGUAikFUurnIP8B7FvSBTQ0WAgAAAAASUVORK5CYII=)