Lodging Deals in the Berkshires

Enjoy the pristine snow of Jiminy Peak by day and the hip vibe of Hotel on North by night with this Ski and Stay Package! Package includes overnight accommodations, 1 full daytime lift ticket at Jiminy Peak Ski Resort per adult per night and 10% off food purchases at Eat on North. Rates from $234 plus tax, based on double occupancy.

Embrace America’s most beloved artist when you visit The Red Lion Inn. Walk the streets of his native Stockbridge. Take an up-close look at the man and his work with passes to the renowned Norman Rockwell Museum. Includes choice of accommodation, a $50 dining credit per room per night, valid toward food and drink purchases at any Red Lion Inn restaurant, and two tickets to the Norman Rockwell Museum, per night. Rates from $200 plus tax per night.

Enjoy our straight-up best rates in our Best Available at Check-in rooms when you book you 2-night or more stay, checking in Monday, Tuesday, or Wednesday only. These special rates do not include breakfast.

Plan your next getaway with Wyndham® Extra Holidays and save! Call 1-800-989-6901 and mention code AFFIL to book your next trip now! Book and travel by December 31, 2018. A two-night minimum stay is required. Offer based on availability and subject to change. Valid for new reservations only. Not valid with other promotional offers. Blackout dates and other restrictions may apply.

Save up to 25% off your stay in the Berkshires! This relaxing resort features spacious 2 bedroom villas with complete with living rooms and fully-equipped kitchens close to all outdoor and cultural attractions. Book now through January 7th with travel dates now through March 31, 2019. Restrictions apply.

Unwind from the stress of daily life and rejuvenate with a getaway to the Inn at Stockbridge. Our on-call massage therapists ensure your spa experience is unforgettable.

Whether you’re planning a surprise Berkshires getaway for your special someone, celebrating an anniversary or seeking a romantic weekend just for two, the Inn at Stockbridge offers an enchanting setting where lifelong memories are made.

Take a break from busy and run away to romance. Hotel on North is the perfect romantic getaway in the heart of Berkshires. Package includes overnight accommodations and a $50 Dining Credit for Eat on North plus a bottle of wine. Rates from $194 plus tax.

When you just need to be pampered, stress no more….come to the Inn at Stockbridge and stay in our luxurious suites, enjoy two home-cooked breakfasts, and two relaxing massages for $650 + tax. Two nights minimum required, subject to availability, excludes holidays, special event weekends and Summer (July and August) and Fall (October). You must call to book this special package!

Enjoy the acclaimed and exquisite culinary creations at our fine dining restaurant, Table Six with a luxurious two or more night stay at our beautiful property. Available year round on Tuesday through Sunday night arrivals.

Available year round this package combines special reduced rates on a two or more-night stay, with complimentary $50 bar credit, a $50 gift certificate for local shopping and two adult admission tickets ($40 value) to world class Berkshire attractions.

Available Sundays year-round, this package is designed to make the most of a wonderful Sunday, from brunch or dinner, to museums, to a restful evening.

This holiday season, buy a Red Lion Inn Gift Card for someone on your list and you will receive a gift as well! Purchase a gift card for $250 or more and receive your own $25 card in return. For a $500 or more purchase, receive $50. Red Lion Inn Gift Cards are redeemable anywhere in the Inn, from The Gift Shop to any one of our dining rooms or for over-night accommodations in the Main Inn or Guest Houses. Purchase must be made by December 15, 2018.

Our vintage motel has been transformed into a hip and homey modern motor lodge. Nestled at the base of Monument Mountain and tucked between Stockbridge and Great Barrington, Briarcliff Motel offers a totally fresh lodging experience in The Berkshires. In celebration, we are offering guests an advance purchase discount of 15% for any booking made at least 7 days in advance!

Come and spend some quality time with your special someone! This package available in our Superior (101, 204) and Deluxe (201, 202, 207) King Rooms for a two or more-night stay, year-round.

Eat & Stay on North wraps up the perfect getaway with one big fat bow for you. Enjoy a one-night stay with an $80 dining voucher at Eat on North, where you’ll find authentic, honest, delicious food. After a breakfast each morning explore the bounty of the Berkshires from the center of it all at Hotel on North. Rates from $209 per night.

Briarcliff loves Dogs. Our Furry Friends Package includes the nightly pet fee for a simple worry-free booking. All well-behaved dogs are welcome, with no breed or weight restrictions. Let us know your pup’s name and we’ll welcome them warmly at the Briarcliff Motel.

Now you can dine in style and stay in a 250-year-old hotel. This special package includes choice of accommodations and a $100 dining credit per room per night, valid toward food and drink purchases at any Red Lion Inn restaurant. That’s enough to satisfy even the most discriminating appetite. Rates from $210 and up.

Attend a Kripalu program and stay with us — take $20 off any room, anytime.