Romantic Hotels & Resorts in The Berkshires

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Check availability on The Berkshires Romantic Hotels

Best The Berkshires Romantic Hotels

The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Wonderful place to stay"
The price is AU$230
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (854)
"Consistently a clean room with welcoming staff."
The price is AU$197
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
Brook Farm Inn
Gateways Inn & Restaurant
Relax in this serene bedroom with a large bed, two nightstands, and sheer curtains framing the view.

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (189)
"Very well kept property, nice restaurant and is in a great area"
The price is AU$618
includes taxes & fees
18 Aug - 19 Aug
Gateways Inn & Restaurant
1896 House Country Inn & Motels
Welcome to The 1896 House, a serene retreat managed by Brookside Accommodations.

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (432)
"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"
1896 House Country Inn & Motels
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is AU$755
includes taxes & fees
18 Aug - 19 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Deerhill Inn
Stunning two-story house with a front porch and stone wall, set amidst a lush lawn.

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is AU$322
includes taxes & fees
18 Aug - 19 Aug
Deerhill Inn
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Stairs lead to a deck area with a view.

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
The price is AU$394
includes taxes & fees
1 Sept - 2 Sept
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Manor House Inn
Classic elegance abounds in this traditional space, featuring a grand staircase and ornate grandfather clock.

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
The price is AU$504
includes taxes & fees
13 Aug - 14 Aug
Manor House Inn
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Enjoy cooking in this kitchen with a central island, appliances, and ample counter space.

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

8.2 out of 10, Very good, (11)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
The price is AU$414
includes taxes & fees
17 Aug - 18 Aug
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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.

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a quick 1 night stay, but we would have stayed longer if we had the time! The basic suite was very large. The bed was comfortable, kitchen was well stocked with cutlery, wine glasses, etc. The front desk staff was perfectly polite and welcoming. I will say that it wasn't obvious when I booked that one has to do one's own dishes, take out the trash. Luckily I read reviews in advance (after booking) so it came as no surpise. Also I learned from other reviews that any restaurant is a healthy drive away, and no food is served on-site. So we knew going in to bring some snacks, and plan in time to drive to any restaurant. (This is just a minor convenience and I'm glad I read reviews before arriving so we weren't surprised.) We'd stay here again!"
Miriam 1-night trip
Posted 3 days ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Food was great!"
Emily 1-night trip
Posted 9 days ago
The Red Lion Inn