Romantic Hotels in The Berkshires, MA

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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
$150 nightly
The price is $165 total per night
$165 total
Jun 17 - Jun 18
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A library is also provided.
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
$136 nightly
The price is $152 total per night
$152 total
Jun 14 - Jun 15
Total with taxes and fees
If you are ready for a blissful getaway, you and your special someone are sure to love the garden and in-room fireplaces at this romantic condo. Other amenities ...
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
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If you and your special someone are ready for a getaway, you're sure to love the hot tub and al fresco dining at this boutique inn. You'll also appreciate the ...
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
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If you're in the mood for love, consider a stay at this romantic guest house, featuring a garden and a lobby fireplace. You'll also love the luxury bedding and ...
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
$121 nightly
The price is $135 total per night
$135 total
Jun 22 - Jun 23
Total with taxes and fees
If you're in the mood for love, consider a stay at this romantic hotel, featuring a garden and onsite dining. You'll also love the terrace and bar.
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
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Rekindle the spark in your relationship. Book a romantic getaway at this guest house where you and your special someone are sure to love the hot tub 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 hotels essential information

Accommodation
1,100 hotels
Lowest Price
$135
Highest Price
$165
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

The Red Lion Inn

The Red Lion Inn

4 out of 5
Posted 3 days ago
Travelocity Verified Review
"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."
A verified traveler stayed at The Red Lion Inn
The Red Lion Inn

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