A person snowboarding down a snowy slope.

Find Romantic Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 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.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
AED 496
AED 775 total
includes taxes & fees
19 Oct - 20 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.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
A house with a covered porch and a well-maintained garden.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A bedroom with a large bed, a chair, a radiator, and a bookshelf.
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.
A cozy room with a wooden bench, a small table, and a chair.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
AED 841
AED 1,781 total
includes taxes & fees
19 Oct - 20 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.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A staircase with a stone wall on one side and a wooden handrail on the other.
A cozy living room with a stone wall, a fireplace, and a chandelier.

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 551
AED 994 total
includes taxes & fees
2 Nov - 3 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.

5. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 465
AED 1,051 total
includes taxes & fees
19 Oct - 20 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A patio with a table and chairs, a grill, and a view of a lake.
A room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
A two-story house with a garage, a driveway, and a river in the background.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.

6. 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 1,031
AED 1,795 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.

7. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A wooden deck with a grill, a table, and chairs.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.
A two-story house with a front porch, a small garden, and a mailbox.

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
United States
Anita T.
AED 691
AED 1,452 total
includes taxes & fees
20 Oct - 21 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.
A two-story building with a steeply pitched roof, a front door, and a staircase leading to a deck.
A compact living space with a brown leather sofa, a dining table with chairs, a kitchen area, and a fireplace.
A bunk bed room with a patterned rug, a window, and a bedside table.

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
United States
Tania J.
AED 203
AED 1,135 total
includes taxes & fees
19 Oct - 20 Oct
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.
A two-story house with a gravel driveway leading to a garage.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.

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
United States
stephen r.
AED 3,269
AED 5,410 total
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 21 hours ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

Explore a world of travel with Expedia