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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for The Berkshires romantic hotels

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (301 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
The price is AED 496
AED 775 total
includes taxes & fees
30 Oct - 31 Oct
Berkshire Village Carriage House - Super Private!!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AED 1,392
AED 2,552 total
includes taxes & fees
16 Nov - 17 Nov
Secluded Family Home in Serene Stockbridge Woods
A kitchen with white cabinets, a wooden dining table, and pendant lights.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,768 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

4. 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, (117 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is AED 496
AED 923 total
includes taxes & fees
5 Nov - 6 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (55 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is AED 393
AED 787 total
includes taxes & fees
4 Nov - 5 Nov
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

6. 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 465
AED 1,055 total
includes taxes & fees
1 Nov - 2 Nov
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A patio with a table and chairs, a grill, and a view of a lake.

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
10.0 out of 10, Exceptional, (75 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 1,722 total
includes taxes & fees
1 Nov - 2 Nov
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

8. 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, (117 reviews)
"enjoyed our week at this property"
United States
cory p.
The price is AED 691
AED 1,440 total
includes taxes & fees
30 Oct - 31 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

9. 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 246
AED 1,154 total
includes taxes & fees
1 Nov - 2 Nov
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A modern kitchen with white cabinets, a large island, and a skylight.

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, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is AED 3,269
AED 5,410 total
includes taxes & fees
30 Oct - 31 Oct
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Rooms were clean, nice beds and new kitchen accessories."
Linda 1-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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