Romantic Hotels in The Berkshires, MA

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Featured 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 $110 total per night
$110 total
per night
Apr 9 - Apr 10
Shaker Mill Inn features free WiFi in public areas and a library. There's free parking if you drive.
Breakfast included
Parking included
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
The price is $141 total per night
$141 total
per night
Apr 6 - Apr 7
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
The price is $127 total per night
$127 total
per night
Apr 9 - Apr 10
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and tours or tickets. Additional amenities include a conference center, a 24-hour business center, and a computer station.
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
Guests of Kemble Inn enjoy free WiFi in public areas, a hot tub, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with tours/tickets and luggage storage. Other amenities at this boutique inn include coffee/tea in a common area, a library, and free newspapers.
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Monterey MA
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
The price is $374 total per night
$374 total
per night
Apr 18 - Apr 19
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. Helpful staff is there to provide a safe deposit box at the front desk, as well as offer insight about the area. Additional amenities include a sauna, free WiFi in public areas, and an outdoor tennis court.
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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 hotels essential information

Accommodation
1,124 hotels
Lowest Price
$110
Highest Price
$374
Popular hotels
Shaker Mill Inn, Vacation Village in the Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Dewey, Chestnut Lodge, Kemble Inn, Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Ponds at Foxhollow

Recent Romantic Getaways & Hotels Reviews

Berkshires Untold

Berkshires Untold

5/5 Excellent
"This was the perfect stay in The Berkshires! It is a well decorated, welcoming, clean accommodation that made me feel so sophisticated upon check-in. The lounge area is beautful, and the fireplace is a nice touch. I spent time there at night working on my laptop enjoying the comfortable ambiance. Others also enjoyed the space visiting with each other outside of their rooms. I will stay here again the next time I'm in town, as it's a wonderful value for the area and it's charming, clean, and comfortable. "
A verified traveler stayed at Berkshires Untold
Posted 15 hours ago
Berkshires Untold

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