Title: The Berkshires Romantic Holidays 2025/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Romantic Holidays ## Book a Romantic 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 £335 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 Packages with flights are ATOL protected ## How to find a romantic The Berkshires holiday #### How can I find the best The Berkshires vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to The Berkshires. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino. #### Can I book cheap The Berkshires romantic holidays for two? Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to The Berkshires that start from . Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a The Berkshires romantic getaway? The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure. #### What should I look for in a luxury romantic holiday to The Berkshires? Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service. #### Can I book a romantic hot-tub holiday in The Berkshires? What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter. #### How can I find romantic holidays for couples in The Berkshires that are all inclusive? Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available. #### Can I book a romantic trip to The Berkshires with free cancellation and/or flexible dates? Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print. #### Why should I book my The Berkshires romantic holiday with Expedia? At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing. ## Top Romantic The Berkshires Hotels ![Shaker Mill Inn](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Shaker Mill Inn 2 Oak Street, West Stockbridge, MA - 25 min walk from Tanglewood Music Center Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ... 9.6/10 Exceptional! (397 reviews) "Clean, comfortable, and quiet. It was everything that was advertised." Reviewed on 7 Sept 2025 [](https://expedia.co.uk/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd, Williamstown, MA - 35 min drive from Tanglewood Music Center Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,018 reviews) "Clean, spacious, well designed room with everything needed gir a great stay …. And so much more. The balcony was a great place to sit, gave coffee etc. can’t say enough about the beautiful grounds and amenities like indoor and outdoor pool areas, etc! Enjoyed staying at Vacation Village in the Berkshire ..." Reviewed on 24 Sept 2025 [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG One West Street, Pittsfield, MA - 16 min drive from Tanglewood Music Center Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and ... 7.8/10 Good! (881 reviews) Couples like: on-site spa services, bar, winery tours Travellers say... "It has been more than 10 years since parking garage available" Reviewed on 23 Sept 2025 [](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) [See all 1,108 properties in The Berkshires](https://expedia.co.uk/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 holidays 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Romantic Holiday Destinations > - 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[Romantic Holidays in Venice](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179981/Venice) ## More Holiday Ideas [Flights to The Berkshires](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Hotels](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[The Berkshires Holiday Rentals](https://expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[The Berkshires Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[The Berkshires Holidays](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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,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)