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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for The Berkshires romantic hotels

Terrace/patio

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (288 reviews)
"This place was really great! Better than the photos. Clean and cute and quiet."
United States
Adam J
The price is AED 551
AED 821 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Village Carriage House - Super Private!!
Indoor pool

2. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 507
AED 1,017 total
includes taxes & fees
11 Aug - 12 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

3. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (111 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is AED 496
AED 916 total
includes taxes & fees
9 Aug - 10 Aug
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Outdoor dining

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,031
AED 1,795 total
includes taxes & fees
18 Aug - 19 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Terrace/patio

5. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 466
AED 786 total
includes taxes & fees
18 Aug - 19 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Outdoor pool, a heated pool

6. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 232
AED 1,163 total
includes taxes & fees
6 Aug - 7 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

7. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is AED 698
AED 1,497 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!
Beach

8. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AED 566
AED 1,089 total
includes taxes & fees
10 Aug - 11 Aug
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Coffee/tea maker, fridge, microwave, oven

9. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (110 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is AED 691
AED 1,440 total
includes taxes & fees
6 Aug - 7 Aug
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Coffee/tea maker, fridge, microwave, oven

10. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (14 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AED 3,269
AED 5,410 total
includes taxes & fees
10 Aug - 11 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
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.
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Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"
judy 1-night trip
Posted 3 hours ago
The Red Lion Inn

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