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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for The Berkshires romantic hotels

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Adam J
AED 496
AED 775 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Village Carriage House - Super Private!!

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
United States
John F.
AED 479
AED 983 total
includes taxes & fees
31 Aug - 1 Sep
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
AED 841
AED 1,781 total
includes taxes & fees
9 Sep - 10 Sep
A roomy remodeled retreat close to MassMoCA

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
AED 496
AED 927 total
includes taxes & fees
8 Sep - 9 Sep
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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
United States
Steve
AED 463
AED 881 total
includes taxes & fees
1 Sep - 2 Sep
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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
United States
Tania J.
AED 182
AED 1,115 total
includes taxes & fees
30 Aug - 31 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

7. 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
United States
Mike
AED 1,146
AED 1,953 total
includes taxes & fees
10 Sep - 11 Sep
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
United States
Adam a.
AED 582
AED 1,355 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!

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
AED 691
AED 1,460 total
includes taxes & fees
9 Sep - 10 Sep
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

10. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
United States
william k.
AED 713
AED 1,789 total
includes taxes & fees
3 Sep - 4 Sep
Summer Escape Near Lakes, Trails & Mt Snow
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Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Room was"
Christopher 1-night trip
Posted 7 hours ago
The Cornell Inn, Lenox & The Berkshires

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