Lodging Deals in the Berkshires

Ski & Stay Package

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.

Starts Friday, November 30th, 2018

Expires Saturday, March 23rd, 2019

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Stay and Dine Getaway

Special TWO NIGHT STAY in one of our luxurious Barnside suites with ONE FOUR COURSE MEAL FOR TWO and ONE BOTTLE OF WINE! Only $299 Sunday through Thursday or $339 weekends! Includes full candlelight breakfast each morning.
*Taxes and gratuity not included. Cannot be used in combination with other special offers.

Offer valid for stays between January 10th through February 10th, 2019 OR stays between February 20th and April 30th, 2019. Please mention code W20 when booking.

Starts Thursday, January 10th, 2019

Expires Tuesday, April 30th, 2019

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Mid Week Lodging Special

Stay two consecutive weeknights (Sunday-Thursday) at any Berkshire Elegant Country Inn and save 10% or receive free upgrade at check in, based upon availability. Must call inn to book this special.

Starts Monday, October 1st, 2018

Expires Tuesday, April 30th, 2019

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Furry Friends Package

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.

Starts Tuesday, September 25th, 2018

Expires Tuesday, December 31st, 2019

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Shop, Sip & Stay

The Berkshires’ quaint towns are peppered with beautifully curated boutiques, bookstores, gift shops and Lee Premium Outlets. So grab your friends, hit the shops then relax at The Bistro with a cocktail and dinner! Package includes: Discounted room rate with a $25 Dining certificate to The Bistro located in the hotel along with Lee Prime Outlets discount coupons.

Starts Monday, December 31st, 2018

Expires Friday, May 31st, 2019

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Last Minute Getaway Special

Reserve within 24 hours of intended stay and receive 15% off( Sunday-Thursday or 10% off (Friday & Saturday) on available rooms. This offer cannot be combined with other offers. Must call inn to book this special.

Starts Monday, October 1st, 2018

Expires Tuesday, April 30th, 2019

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Early Booking Deal

It’s never too early to start planning your next Berkshire getaway! For a limited time only we’re inviting you to book early and SAVE 15% on room rates. Applies to new bookings only and cannot be combined with any other offers, discounts or group bookings. Restriction dates apply.

Starts Wednesday, January 9th, 2019

Expires Sunday, March 31st, 2019

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Stay & Play in the Berkshires

Make more of your stay in the Berkshires and save 25% off when you stay at Holiday Inn Club Vacations Oak n’ Spruce Resort! Located in the heart of the Berkshires, our resort offers amenities like an 18-hole mini golf course, arcade, indoor/outdoor pools and much more. All of our spacious villas feature separate bedrooms, living rooms with sleeper sofas, and fully-equipped kitchens making your vacation feel more like home. Your next fun-filled vacation is just a click away. Save 25% when you book today!

Starts Wednesday, January 16th, 2019

Expires Tuesday, December 31st, 2019

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Stay & Dine

Stay 2 nights mid-week (Sunday-Thursday) and receive a $50 gift certificate towards a dinner for two at one of our favorite restaurants. Cannot be combined with other offers and must call inn to book this special.

Starts Monday, October 1st, 2018

Expires Tuesday, April 30th, 2019

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