Book romantic hotels in The Berkshires, MA from CA $144

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Top The Berkshires Romantic Getaways & Hotels

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
The price is CA $207 per night
CA $207
CA $227 total
Nov 15 - Nov 16
includes taxes & fees
Stay at this B&B in West Stockbridge. Enjoy free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II Gifts and Antiques ...
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is CA $115 per night
CA $115
CA $144 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
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Stay at this guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions ...
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
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Book a stay at this boutique inn in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Berkshire Performing ...
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
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Stay at this guesthouse in Lee. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Goose Pond Reservation and Lee Premium Outlets are located ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
The price is CA $150 per night
CA $150
CA $167 total
Dec 11 - Dec 12
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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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.

The Berkshires Romantic Hotels

Is your anniversary quickly approaching? Maybe you’re looking for the perfect honeymoon getaway? Or, has it just been too long since you and yours had some quality alone time away from the hectic schedule of everyday life? Take a steamy trip and stay at one of the most romantic hotels in The Berkshires.

Remember the feeling of first meeting your significant other? You were nervous and excited. It felt like talking to your first crush on the playground. Re-ignite those feelings with an unforgettable stay to one of the The Berkshires romantic hotels. Treat your loved one to a perfect day with breakfast in bed, a day at the spa and then a sultry dinner at a top restaurant in The Berkshires. After dinner, take a moonlit walk through one of the city’s beautiful parks, because nothing says romance like a stroll under the stars. Whether you have been together for a few weeks or 50 years, the romantic hotels in The Berkshires are the perfect weekend getaway for you and your loved one. 

You’ll also be feeling affectionate toward Travelocity when you browse our vast selection of accommodations that cater to couples. We have unbelievable deals on the best romantic hotels in The Berkshires, so you don’t have to worry about breaking the bank for your trip. Book now and let the honeymoon begin.

The Berkshires hotels essential information

Accommodation
1,078 hotels
Lowest Price
CA $144
Highest Price
CA $227
Popular hotels
Shaker Mill Inn, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Dewey, Chestnut Lodge, Kemble Inn

Recent The Berkshires hotel reviews by fellow wanderers

Vacation Village in the Berkshires

Vacation Village in the Berkshires

4 out of 5
Posted 4 hours ago
Travelocity Verified Review
"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."
A verified traveller stayed at Vacation Village in the Berkshires
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

5 out of 5
Posted 20 hours ago
Travelocity Verified Review
"We loved the place & desk staff . Breakfast room staff was curt and dismissive."
A verified traveller stayed at The Red Lion Inn
The Red Lion Inn

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